Water Mill, NY Vacation Rentals

Explore 160 vacation rentals, homes, and villas in Water Mill, NY for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $115 per night and featuring up to 8 bedrooms and 11 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

160 Vacation Rentals in Water Mill

Quaint Water Mill Cottage

Water Mill, NY, US
2 Bedrooms 6 Guests
Sep 11 - 13
$397 night

Quaint Water Mill Cottage Beautiful cottage on meticulously maintained lawn, surrounded by perennials, large deck, and minutes to beaches plus shops and eateries in Water Mill 2BR/2BA - light-filled spaces, stylish dcor, antiques, French doors, serene surroundings, and spacious bedrooms You are warmly invited to a remarkable retreat here at Water Mill Cottage. Checking off every Hamptons wishlist, this home exudes tranquility, serenity and warmth. Nestled in nature, prepare to unwind and take in the beautiful landscape and serene surroundings on this next vacation. Cultivate forever memories with your loved ones and enjoy access to a wealth of amenities. Filled with charm, discover light-filled spaces blended with antiques that add to the allure of this charming home. Whether youre preparing small bites or a grand six-course meal, your well-equipped kitchen is ready for you. Mix up your favorite Summer cocktails or have a wine night to compliment your delicious meals. Comfortably accommodating up to six guests, two airy bedroom suites adorn this home including the Primary prepared with a comfy King bed and ensuite bath. The second bedroom offers queen bed with deck access. Each room is prepared with fresh linens, plush towels and premium bath essentials. Enjoy full scale entertainment or relaxation from your expansive backyard bathed in natures beauty. Prep the grill for some amazing BBQ during your stay or enjoy picnics from the beautiful lawn. Surrounded by picturesque perennials, while the lawn is perfect for outdoor activities, its also a great place to relax. When youre ready to explore, enjoy living just moments to Parrish Art Museum, Duckwalk Vineyards, Shou Sugi Ban Wellness Resort & Spa plus Hanks Pumpkin Patch & Apple Orchard. Grab a bike and head over to the nearby beaches as well including Flying Point and Coopers Beach then dinner at one of many fine dining options along Montauk Highway. Experience an unmatched and stellar way to vacation in Water Mill. This property has a max occupancy of 6 Bedrooms Primary Bedroom: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet, Balcony/Deck Additional sleeping space: One Sleep Sofa, First Floor/Main Floor Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Jack & Jill, Shower/Tub Combo TVs Primary Bedroom: Streaming Bedroom 2: Streaming Outdoors Deck/Patio, Lounge Chairs (2 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Beach Chairs (4 Chairs), Beach Umbrella, Cooler, Fence Around The Yard, Kayak/Canoe, Outdoor Shower (Hot + Cold Water) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Nespresso, Pot), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Cable TV, Smart TV, Speaker System (Bluetooth Speaker), Private Entrance, Parking (4 Cars In Driveway), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Iron/Ironing Board, Laptop-Friendly Workspace, Pots and Pans Special Features Pretty perennial gardens, lawn for playing games, secluded and quiet, fenced in backyard. Walking distance to Parrish Art Museum, Duckwalk Vineyards, Shou Sugi Ban Wellness Resort & Spa and Hanks Pumpkin Patch & Apple Orchard Location Nearby Beaches: Flying Point Beach, Water Mill, Cooper’s Beach, Southampton Nearby Grocery Stores: Citarella Gourmet Market, Provisions Natural Foods, King Kullen, Stop & Shop Nearby Restaurants and Bars: Bistro Ete, Suki Zuki, Lunch Lobster Roll, 75 Main, Union Burger Bar, Bobby Vans, Almond, Pierre’s, Sant Ambroeus Other FAQ’s Backyard Fenced In: Yes Estimated Square Footage: 1,215 0.4 Acres. Children and pets on property at own risk. Suitability: Primary renter must be at least 25 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $75.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Water Mill Towd Terrific

Water Mill, NY, US
6 Bedrooms 16 Guests
Sep 11 - 18
$2,693 night

Please note that a reservation for this property needs to be approved before it is confirmed. Water Mill Towd Terrific Beautiful home with private pool, hot tub, gym, pool table, ping pong, fire pit and more! 6BR/7.5BA: Close to town, spacious living, minutes to Southampton Village and Sag Harbor Escape to the Hamptons all season round and enjoy a rejuvenating stay at Water Mill Towd Terrific. Idyllically located, you are just minutes from town and the beautiful sands of local beaches. Perfect for large families or friend groups, you are sure to feel right at home and away from the monotony of daily life. This enchanting, storybook home with fabulous outdoor space boasts beautiful, grand spaces and an impressive floor plan with effortless flow. Rest assured, there are activities and stylish rooms for every mood including a spacious Great room with a fireplace, wine cellar, game room with billiards, movie theater, and cozy separate rooms for your moments of solitude. Prepare your favorite meals or hire a private chef to entertain from the beautiful Chefs kitchen featuring a large bar top and center island. Six serene bedrooms encompass this home including two Primary suites, each with a walk-in closet, balcony and ensuite bath. The luxe primary bath is a personal spa moment featuring a deep soaking tub and walk-in shower. The finished lower level offers additional open space including the sixth bedroom suite. Spanning over one lush acre of land, the outdoor area is filled with both entertainment and relaxation options including a rooftop terrace, large Gunite pool, spa, patio area as well as a deep front porch. Host gatherings for friends easily from the outdoor kitchen. Relax one evening under the stars with a picnic or sip cocktails as you lounge by the pool. The opportunities for enjoying the last days of summer are endless. When youre ready to venture out to enjoy the classic Hamptons, you are just minutes from Southampton Village, Southampton, and Sag Harbor plus some of the most pristine beaches on the East coast. Indulge in the best of local seafood but also take in the farmers markets and small town charm. Welcome home! This property has a max occupancy of 16 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, Closet Bedroom 2: One Queen Bed, Lower Level, Air Conditioning, TV, Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, TV, Walk-in Closet, Balcony/Deck Bedroom 4: Two Bunk Beds, 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet, Balcony/Deck Bedroom 5: One Bunk Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet Bedroom 6: One Double/Full Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet Additional Sleeping Space 1: One Twin Single Bed, 3rd Floor, Air Conditioning, Privacy Additional Sleeping Space 2: One Double/Full Bed, Air Conditioning, Privacy Bathrooms Bathroom 1: Full Bath, Lower Level, Shower Bathroom 2: Half Bath, First Floor/Main Floor Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 4: Full Bath, First Floor/Main Floor, Handicap Accessible, Shower Bathroom 5: Full Bath, 2nd Floor, Ensuite, Handicap Accessible, Shower, Tub Bathroom 6: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 7: Full Bath, 2nd Floor, Ensuite, Handicap Accessible, Shower/Tub Combo Bathroom 8: Full Bath, 2nd Floor, Ensuite, Handicap Accessible, Shower TVs Bedroom 2 Bedroom 3 Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (8 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Wood-Burning), Outdoor Shower (Hot + Cold Water), Balcony, Beach Chairs (4 Chairs), Beach Umbrella, Beach Toys, Cooler, Fence Around The Yard, Private Pool (Outdoor, Heated, Saltwater), Hot Tub Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Coffee (Pot, Keurig), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Pack 'n Play/Travel Crib, Gym/Fitness Room (Elliptical, Treadmill, Stationary Bike, Weight Training Equipment, Stretching / Yoga Mat), Game Room, Ping Pong Table, Pool Table, Private Entrance, Parking (6 Cars In Driveway), Garage (2 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Dryer, Laptop-Friendly Workspace, Pots and Pans Location Nearby Beaches: Flying Point Nearby Grocery Stores: Southampton Water Mill Other Location Information: Good location for avoiding traffic Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 6,800 Suitability: Not handicap accessible. Not suitable for unrelated guests. Primary renter must be at least 35 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $140.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Water Mill Retreat

Water Mill, NY, US
4 Bedrooms 10 Guests
Sep 15 - 18
$671 night

Water Mill Retreat Elegant Coastal Escape with Expansive Yard, Heated Pool, and Outdoor Kitchen in the Heart of Water Mill 4BR/4.5BA: Private heated pool, outdoor kitchen and dining, luxurious indoor-outdoor living, chef's kitchen Nestled in the heart of Water Mill, this charming and elegant Hamptons retreat offers a luxurious and timeless escape for the discerning traveler. Perfectly situated just minutes from world-renowned beaches, farm-to-table restaurants, acclaimed wineries, and quaint village shops, the home seamlessly blends classic East End style with modern amenities. Surrounded by lush, manicured landscaping and designed for effortless indoor-outdoor living, this property promises an experience that is as serene and stylish as it is unforgettable. From the moment guests arrive, they are welcomed into a refined sanctuary that feels more like a private resort than a rental home. Step outside and discover the true heart of the estatea sprawling, fenced-in backyard oasis that offers complete privacy and tranquility. The grounds are a verdant haven, ideal for sun-drenched afternoons and magical summer evenings. At the center lies a stunning private heated pool, bordered by multiple sundecks adorned with luxurious chaise loungers. Guests can spend their days unwinding on outdoor sofas around the fire table, sipping morning coffee beneath the shade, or enjoying evening cocktails as the sun sets. The outdoor kitchencomplete with a charcoal BBQ, wood-fired pizza oven, and mini fridgemakes alfresco dining and entertaining effortless. Whether hosting a garden soire or enjoying a quiet moment with a book, every corner of the outdoor space is designed for both relaxation and connection. With ample on-site parking and a seamless connection between the home and its outdoor living spaces, the property delivers an unparalleled resort-style experience. Not to mention the pristine outdoor private shower available to rinse off after day in the sand and sun. Inside, the home welcomes guests with the quintessential charm of Hamptons architecturebright, breezy spaces with sophisticated finishes and elegant furnishings throughout. The traditional layout begins with a formal living room that exudes classic comfort, complete with a plush sectional, cozy fireplace, and oversized bay windows that bathe the room in natural light and offer sweeping views of the backyard. Glass doors open directly to a main level patio with outdoor table and chairs and gas BBQ, a beautifully designed area that sets the perfect stage for evening aperitifs or nightcaps. The adjacent dining room is equally refined, featuring a large table that comfortably seats eight, ideal for lingering over leisurely meals with friends and family. The heart of the homethe gourmet kitchenis a chefs dream. Outfitted with top-of-the-line appliances, a spacious island, and every essential needed for entertaining, its a space designed for both function and beauty. From morning coffee to multi-course dinners, the kitchens thoughtful layout and modern elegance elevate every culinary moment. Flowing easily from the kitchen and living room, the indoor spaces open gracefully to the outdoor entertaining areas, creating a seamless harmony between inside and out. The finished lower level offers an additional layer of comfort and versatility. Guests can unwind in a second living space complete with two couches, flat-screen TV, fireplace, and additional sleeping space with a queen sleeper sofa. The double glass doors open to provide direct access to the backyard and pool, while a full bathroom with a walk-in shower and a convenient laundry area, plus additional refrigerator, freezer and commercial ice maker, ensure that every need is met. Accommodations throughout the home are thoughtfully appointed and stylishly designed to ensure the ultimate in rest and relaxation. The second-level primary suite is a private haven, featuring a king bed, its own fireplace, a chic sitting area, and a make-up vanity. The spa-like ensuite bathroom is a retreat in itself, offering double sinks, a jacuzzi tub, and a luxurious walk-in showerthe perfect way to unwind after a day of Hamptons adventures. Two additional guest bedrooms are located on the upper level, both offering serene dcor and access to a shared jack-and-jill bathroom with tasteful finishes. On the first floor, an additional guest suite with a queen bed and a private ensuite bathroom, also with an enclosed shower and jacuzzi tub, is ideal for those seeking single-level comfort and privacy. The lower level also features a sleek full bathroom with additional sleeping area, while a stylish powder room on the main floor adds a touch of convenience for entertaining. Beyond the home, the best of the Hamptons is at your fingertips. The nearby towns of Bridgehampton and Southampton are just minutes away and offer a curated mix of luxury boutiques, art galleries, and gourmet dining. Spend a leisurely afternoon exploring local vineyards, sampling award-winning wines, or browse nearby antique shops and high-end home dcor stores. The areas pristine beachessome of the most coveted on the East Coastare within a short drive and offer sweeping ocean views, soft sand, and refreshing sea breezes. Whether guests are looking to catch a morning surf, enjoy an evening beach stroll, or indulge in fresh lobster rolls with their toes in the sand, the shoreline is always close. For a cultural touch, visit local art institutions like the Parrish Art Museum or take in a performance at the nearby performing arts centers. Ideal for family getaways, couples retreats, or small groups of friends, this Water Mill estate offers more than just a place to stayit offers a full lifestyle experience. With its timeless Hamptons charm, beautifully curated spaces, and seamless access to both relaxation and recreation, this is more than a homeits a destination in itself. *Please note that for any bookings that exceed 7 nights, the cost of propane for the pool heating is not included. A propane deposit will be collected at the time of booking and the guest will be charged based on usage at the conclusion of the rental period. This property has a max occupancy of 10 Bedrooms Bedroom 1 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Guest: One King Bed, 2nd Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 3 - Guest: One Queen Bed, 2nd Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, TV, Closet Bedroom 4 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Lower Level Sleeping Area: One Sleep Sofa, Lower Level, Air Conditioning, Ensuite Bathroom, TV, Privacy Bathrooms Bathroom 1 - Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Powder Room: Half Bath, First Floor/Main Floor Bathroom 2 - Jack and Jill: Full Bath, 2nd Floor, Ensuite, Jack & Jill, Shower Bathroom 3 - Primary Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4 - Lower Level: Full Bath, Lower Level, Shower TVs Bedroom 1 - Guest: Streaming Bedroom 2 - Guest: Streaming Bedroom 3 - Guest Bedroom 4 - Primary: Streaming Lower Level Sleeping Area Outdoors & Pool/Spas Deck/Patio (Uncovered), Grill (Gas, Charcoal), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fire Pit (Gas), Outdoor Shower (Hot + Cold Water), Beach Chairs, Beach Umbrella, Cooler, Fence Around The Pool, Fence Around The Yard, Private Pool (Heated, Outdoor, Freshwater) Amenities Bed Linens, Usable Fireplace (Wood-Burning, Gas-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Essentials, Smart TV, Laptop-Friendly Workspace, Wine Fridge, Iron/Ironing Board, Blender, Speaker System (Bluetooth Speaker), Parking Special Features Incredible central location in Water Mill. Minutes to Southampton Village, Bridgehampton and Sag Harbor. Location Nearby Beaches: Flying Point Beach W. Scott Cameron Beach Ocean Road Beach Nearby Grocery Stores: Citarella, Stop and Shop, Red Farm Market, Seven Ponds Farm Stand, Halsey Farm & Nursery, Clam Man Seakfood, Peconic Meats Nearby Restaurants and Bars: Duck Walk Hamptons Goldberg’s Bagels Calissa Bistro Ete Other Location Information: Parish Art Museum Water Mill Museum Southampton Art Society Guild Hall Stephen Talkhouse (live music) Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 3,000 A pool fence can be provided for an additional $600, including installation and removal. Rental Registration: 250557. Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: One dog of 30 lbs or less is permitted for an additional $100.00 per booking. Dogs over 30 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $125.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $25.00 per person per night may be required. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Deer Ridge Dream

Water Mill, NY, US
5 Bedrooms 12 Guests
Sep 15 - 19
$824 night

Please note that a reservation for this property needs to be approved before it is confirmed. Deer Ridge Dream Private setting with treetop views, resort style pool and jacuzzi, fully equipped gym, and the perfect escape for groups close to Bridgehampton, Southampton, and Sag Harbor. 5BR/4BA: Enjoy the fireplace, large deck, heated pool, jacuzzi, secondary living room, double washer and dryer, private gym, and spacious indoor and outdoor dining areas. Deer Ridge Dream sits on a beautiful and peaceful private block, offering guests a true retreat from the bustle of daily life. Perfectly situated close to Bridgehampton, Southampton, and Sag Harbor, this stunning five bedroom, four bathroom escape welcomes groups and families looking to reconnect, relax, and unwind. Its open floor plan creates the ideal backdrop for gatheringwhether enjoying slow mornings surrounded by treetop views or settling in after a day exploring the charming nearby villages. This is the kind of home travelers return to year after year: warm, thoughtfully designed, and crafted for memorable stays. Stepping onto the property, guests immediately feel the sense of total privacy that defines Deer Ridge Dream. Surrounded by lush greenery and elevated natural landscapes, the home offers an outdoor setting that feels worlds away. A large deck invites lounging and long conversations, while the resort style heated pool and soothing jacuzzi create a spa-like atmosphere perfect for both relaxation and fun. Whether groups are sunbathing, grilling, sharing meals outdoors, or taking an evening dip beneath the stars, the exterior spaces are designed to encourage connection and effortless enjoyment. Treetop views wrap around the home, offering a rare blend of nature, seclusion, and luxuryan ideal environment for unforgettable gatherings. Inside, the open layout instantly welcomes guests with a sense of space, flow, and calm. Sunlight pours through oversized windows, filling each room with a gentle warmth throughout the day. The main living area blends seamlessly into the dining room and gourmet kitchen, making it easy for everyone to stay connected no matter where they choose to relax. The kitchen is fully outfitted with top tier appliances, a high end coffee maker, ample prep space, and everything needed for preparing meals or hosting dinners at home. Whether cooking together, enjoying takeout from a favorite local spot, or hiring a private chef, guests will find the kitchen both stylish and functional. Additional conveniences such as strong WiFi, central air conditioning, and a double washer and dryer ensure comfort throughout every stay. With multiple living spacesincluding a cozy secondary living room with fireplaceguests can gather together or spread out as they wish, allowing the home to perfectly support both group time and personal relaxation. The five beautifully appointed bedrooms offer serene sanctuaries for rest. Each room is thoughtfully furnished with soft lighting, comfortable mattresses, and fresh hotel-quality linens to ensure a restorative nights sleep. The four bathrooms are equipped with clean modern fixtures, plush towels, and all the essentials guests might need throughout their stay. Whether preparing for a day of adventure or winding down in the evening, every bedroom and bathroom is designed to create a sense of comfort and ease. The homes private gym provides an added luxury for guests looking to maintain their wellness routine, making it possible to work out without ever leaving the property. As the day comes to a close, guests can enjoy the beauty of the Hamptons just minutes away. Deer Ridge Dream is ideally located near world-class restaurants, charming shops, celebrated art galleries, and scenic golf courses. Some of the most breathtaking beaches in the region are only a short drive away, offering endless opportunities for sun, sand, and shoreline strolls. Whether travelers crave relaxation, exploration, or a bit of both, this home serves as the perfect home base for experiencing everything the area has to offer. Warm, inviting, and perfectly tailored for groups, Deer Ridge Dream delivers a luxurious private escape with all the comforts of homean experience designed to be savored, remembered, and repeated. This property has a max occupancy of 12 Bedrooms Master Bedroom: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Cable TV, Closet, Balcony/Deck Bedroom 2: One Queen Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Closet, Balcony/Deck Bedroom 3: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, Streaming TV, Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Closet, Balcony/Deck Bedroom 5: One Queen Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Streaming TV, Closet Bathrooms Master Bathroom: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 3: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 4: Full Bath, First Floor/Main Floor, Shower, Tub TVs Master Bedroom: Cable Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 4: Streaming Bedroom 5: Streaming Outdoors & Pool/Spas Beach Chairs (4 Chairs), Lounge Chairs (5 Chairs), Deck/Patio, Balcony, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fence Around The Pool, Outdoor Shower, Private Pool (Outdoor, Heated), Hot Tub Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning (Central Air), Heating, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Usable Fireplace (Wood-Burning), Internet (Wifi), Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Blender, Speaker System (Stereo), Television (Den), Private Entrance, Parking (5 Cars In Driveway), Garage (1 Cars In Garage), Living Room, Kitchen, Carbon Monoxide Detector, Smoke Detector, Essentials, Hot Water, Refrigerator, Gym/Fitness Room (Treadmill), Cable TV, Ice Maker, Laptop-Friendly Workspace, Pots and Pans, Stove, Oven, Dishwasher Special Features Right in the middle of the Hamptons, so not too long a drive to all towns. 5 mins drive to Water Mill town Center. 12 mins drive to Southampton and Bridgehampton town center. 20 mins drive to Sag Harbor town center. Location Nearby Beaches: Flying Point Beach Cooper’s Beach Foster Memorial (Long Beach) Mecox Beach Sagg Main Beach W. Scott Cameron Beach Nearby Grocery Stores: King Cullen (Bridgehampton Commons) Stop & Shop (Southampton) Stop & Shop (East Hampton) Porcos Country Deli & Pizza Close to multiple farm stands Citrella (Southampton) Citrella (Bridgehampton) Clamman Seafood Market Peconic Prime Meats Schmidt’s Market & Produce Schiavoni’s Market Provisions Health Food Store Nearby Restaurants and Bars: Suki Zuki Coast Grill Bell & Anchor 75 Main St. Ambroes Tutto Il Giorno American Pie Pizza Scoop Du Jour Aldo’s La Hacienda Mexican Grill Calissa Sabrosa Pierre’s Almond Bobby Van’s Elaia Esiatorio Yama Q Jean-Georges Topping Rose House Grindstone Coffee & Donuts Il Capuccino Sen Japanese Sushi Wollfer Kitchen Dopo La Spiaggia Le Biloquet Beacon Other Location Information: Close to Tennis and Golf Parish Art Museum Close to wine and vineyards (Duck Walk Vineyard 5 mins away) Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: No Estimated Square Footage: 3,500 Suitability: Not handicap accessible. Primary renter must be at least 25 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $75.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Available Year Round Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Water Mill Wooded Escape

Water Mill, NY, US
4 Bedrooms 8 Guests
Sep 12 - 14
$1,344 night

Water Mill Wooded Escape Designer Gut Renovated Farmhouse on over 1 Acre, Numerous Spacious Living Areas with Modern Amenities, Scenic Backyard with Gunite Pool, Hot Tub, and Gas Fire Pit 4BR/5.5BA with living room, chef’s kitchen, island fireplace, grill, pool and pool house, hot tub, fire pit, outdoor shower, fitness room, sauna, basketball court Experience luxurious indoor-outdoor living at this modern designer farmhouse surrounded by nature in Water Mill. The 5,700 square-foot stylish and cozy interior is full of natural light and bright living spaces. As you drive up to the house, you will notice the sizable front porch, an ideal place to bask in the crisp Hamptons air. Relax in the cheerful living room surrounded by windows and sliding glass doors in front of the gas fireplace. Whip up a hearty brunch in the chef’s kitchen with a Wolf wine fridge, top-of-the-line stainless steel appliances, and a sizable quartz island. On the island with three chairs, sip a fresh cup of home-brewed coffee or cappuccino with the morning paper. Share a meal at the chic six-person dining table overlooking the backyard. Play pleasant music in the background, inside and outside, using the Sonos speaker system. Congregate in the den areas with plush furniture and flat-screen TVs. The private, scenic backyard with bluestone patios is ideal for entertaining and unwinding with friends and family. Fire up meat and veggies on the gas grill to enjoy al fresco on the comfortable patio furniture, including a table and plush couches. Soak up the sun with a cool drink poolside from the four lounge chairs. Take a refreshing dip and float around the heated, freshwater gunite pool. On cooler nights, decompress in the hot tub and tell stories around the gas fire pit. Work up a sweat in the fitness room containing a treadmill, Tonal system or weight training equipment or on the home’s basketball court before hitting the infrared sauna. Afterward, use the outdoor shower with hot and cold water. The sleek, custom-designed 900-square-foot pool house provides additional living and entertaining space with a TV and full bathroom. When you’re ready to explore, you are minutes from restaurants, shops, and activities for the whole family in Watermill, Bridgehampton, and Sag Harbor. At the end of a sun-soaked day, get a good night’s sleep in the four spacious bedrooms, each with a full ensuite bathroom. The primary suite features a gas fireplace and a balcony, ideal for sipping your morning coffee or enjoying a nightcap before sleep. Water Mill Wooded Escape is an unforgettable Hamptons retreat. This property has a max occupancy of 8 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Walk-in Closet, Balcony/Deck Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Walk-in Closet Bedroom 4: Two Double/Full Beds, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, TV, Closet Bathrooms Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4: Full Bath, Lower Level, Ensuite, Jack & Jill, Shower Bathroom 5: Half Bath, First Floor/Main Floor Bathroom 6 - Pool House: Full Bath, Pool House First Floor/Main Floor, Shower TVs Bedroom 1 Bedroom 2 Bedroom 3 Bedroom 4 Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Basketball Court, Fire Pit, Outdoor Shower (Hot + Cold Water), Balcony, Fence Around The Yard, Private Pool (Outdoor, Heated, Freshwater), Hot Tub Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Gas), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room, Additional Structure (Pool House, guest house, detached garage)), Smart TV, Sauna, Gym/Fitness Room (Treadmill, Weight Training Equipment), Private Entrance, Parking (8 Cars In Driveway), Electric Vehicle Charger, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Wine Fridge, Coffee (Other), Speaker System (Sonos) Other FAQ’s Estimated Square Footage: 4,250 Suitability: Not suitable for unrelated guests and persons with disabilities. Primary renter must be at least 30 years old. Pet Policy: One hypoallergenic/non-shedding dog permitted. Non hypoallergenic/shedding dogs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). An additional security deposit of $500.00 per dog will be required. Utility Disclaimer: Normal usage of the following utilities is included in the total reservation amount: Pool Heating (if applicable), Pool/Hot-Tub Maintenance (if applicable), Heating Oil/Propane/Natural Gas, Electricity, Cable/TV/Internet/Phone, Garbage Removal, Landscaping/Lawn Maintenance, and EV Car Charging If the cost of utilities exceeds $135.00/night, guest will be responsible for the difference. Cleanings during a guest’s stay and pay-per-view orders are not included in the cost of utilities. Cleaning Disclaimer: All reservations longer than one week must be professionally cleaned once per week, the cost of which is borne by the guest. For clarity purposes, the cost of in-stay cleanings are separate and above the fees collected at the time of booking. Additional Persons: No additional persons beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. StayProtected Insurance: Property damage insurance is procured for your reservation for this property. It is supplemental to, not a replacement to, any security deposit collected. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.

Tuckahoe Woods Wonder

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 13 - 15
$732 night

Tuckahoe Woods Wonder Beautiful Southampton Home Minutes from Beaches, Nature Preserve, Golf Courses, Town Shopping and Restaurants 4BR/3BA: heated pool, gas fire place, gas fire pit, sonos speakers, Nespresso coffee, expansive outdoor space, work-from-home set-up Escape to the Hamptons and stay in this beautiful Southampton home, Tuckahoe Woods Wonder. Perfect for families, this spacious home features four bedrooms and three bathrooms, providing plenty of room for everyone to relax and unwind. Situated on a beautiful private block, this home is the perfect retreat for those looking to escape from the hustle and bustle of daily life. As you step inside, you’ll immediately feel at home in this warm and welcoming space. The open layout allows for plenty of natural light to filter through the home, creating an airy and bright ambiance. The living spaces are perfectly designed for comfortable family living, with an easy flow from the living to the dining room and kitchen. The island kitchen features top-of-the-line appliances, making meal preparation a breeze. After dinner, gather around the living room fireplace and watch your favorite movies on the big screen TV. With easy access to the back patio, this home truly has it all. Outside, you’ll find a myriad of amenities to enjoy. Total privacy is yours to enjoy, as the expansive patio is surrounded by lush greenery. Dine al fresco at the outdoor dining table, fire up the gas BBQ for a delicious summer feast, or relax in one of the multiple sitting areas, perfect for sipping cocktails with friends and family. As the sun sets, gather around the gas fire pit and enjoy the warmth of the fire as you share stories and make memories with your loved ones. Retreat to one of the four beautifully appointed bedrooms, each offering fresh linens and all the essential amenities you need to feel right at home. With three bathrooms, everyone in your group will have plenty of space and privacy to get ready for the day ahead. Whether you’re traveling with family or friends, this home provides a perfect respite from the hustle and bustle of daily life. When you’re ready to explore the area, you’ll find plenty to see and do. Southampton is renowned for its beautiful beaches, where you can spend hours lounging in the sun or taking a refreshing dip in the ocean. In town, you’ll find an array of charming shops, art galleries, and restaurants to explore, providing a true taste of the Hamptons lifestyle. Just minutes away, you’ll find the picturesque towns of Sag Harbor and Water Mill, each offering their own unique charm and character. For nature enthusiasts, the Tuckahoe Woods nature preserve is just a short drive away, offering miles of scenic trails to explore. This property does have external security cameras. There are no cameras on the interior and the exterior cameras do not point towards the house. This property has a max occupancy of 8 Bedrooms Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 2: One Bunk Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Primary Bedroom 3 primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet, Balcony/Deck Bathrooms Bathroom 1: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 2: Full Bath, First Floor/Main Floor, Shower/Tub Combo Master bathroom Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower TVs Bedroom 2: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs), Grill (Gas), Fire Pit (Gas), Beach Chairs (8 Chairs), Cooler, Fence Around The Yard, Beach Umbrella, Private Pool (Outdoor, Heated, Freshwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Main Living Room, Den), Smart TV, Speaker System (Sonos), Private Entrance, Parking, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Electric Vehicle Charger Location Nearby Beaches: Coopers Beach, Cryder Beach, Halsey Neck Beach, Little Plains Beach Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 2,600 Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $135.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Oceanstone | Villa w/ Beach Access

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 26 - 29
$1,478 night

Welcome to Oceanstone, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Introducing Oceanstone, an exquisite Southampton retreat just moments from the ocean. This five-bedroom, six-bathroom (5 full, 2 half baths) estate spans 5,680 square feet across three levels, offering refined elegance at every turn. Inside, high-end finishes and thoughtful details define the space—an inviting living room with a fireplace, a chef’s kitchen with top-tier appliances, and a formal dining area featuring a second fireplace. Lined with French doors, the dining space opens onto a covered back porch, creating a seamless indoor-outdoor living experience. Upstairs, the primary suite offers a private balcony and spa-like bath, while additional en-suite bedrooms provide comfort and privacy. The third level features a versatile space, ideal as a home office, study, or media room, all with inspiring views. Outside, a pristine heated gunite pool is the centerpiece of the landscaped backyard, creating the perfect setting for sun-soaked days and evening gatherings. Enjoy seamless access to the nearby beach, with just a short and enjoyable walk away from this residence. Whether you’re here to unwind or entertain, this beautifully designed residence delivers an unparalleled blend of luxury and serenity in the heart of Southampton. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are allowed with approval and a one time $150 charge. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. We are looking for considerate guests who appreciate the calm, exclusive character of the neighborhood and will treat the home with care and respect. Full house guidelines will be shared in the welcome pack upon check-in. Please note that both fireplaces on the ground floor are for decorative purposes only and cannot be used. The pool is open seasonally. It is professionally cleaned and chemically balanced weekly; however, as an open-air pool, natural debris between service visits is normal. A skimmer net is provided for your convenience, and our team is always happy to assist if needed. Pool heating is available for an additional $75/night and temperature is kept at 75°F under normal operating and weather conditions. Outdoor pool temperatures may vary based on weather, usage, and other external factors. While we make every effort to ensure the heater is functioning properly, pool heating cannot be guaranteed at a specific temperature at all times. In the unlikely event the heater is unavailable due to a mechanical or service issue, pool heating fees will be refunded. Utilities, including pool heating, are billed separately for stays over 14 nights. The home is just a short walk from the beach. For guests who wish to drive, parking passes are available for $50 per day. As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property. From October–April, the bathroom above the garage is closed to protect plumbing from freezing. All other bathrooms remain fully available. Security deposit Stays up to 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

Bullhead Bay Beauty

Southampton, NY, US
3 Bedrooms 6 Guests
Sep 11 - 13
$641 night

Bullhead Bay Beauty Southampton Bullhead Bay Private Home, Fenced in Yard, Great for Families 3BR/2BA: Private Southampton Serene Escape, Patio, Fire Pit, Steam Room, Quiet Enjoyment Tucked along a beautiful and private block near Southamptons Bullhead Bay, this serene 3-bedroom, 2-bath retreat offers families and small groups a peaceful escape from the rhythm of daily life. With an inviting open floorplan and sleeps up to 6, the home is designed to make every moment feel relaxed and effortless. Sunlight pours through expansive windows, illuminating spaces meant for gathering, unwinding, and reconnecting. Its the kind of home where mornings begin slowly with coffee on the patio and evenings end around the fire pit beneath a canopy of starsan ideal setting for families seeking tranquility without sacrificing comfort or convenience. Outside, the propertys thoughtful design emphasizes privacy and simple pleasures. A fully fenced-in yard provides a secure, secluded outdoor sanctuary where children can play freely and adults can savor the quiet. Mature landscaping frames the home, offering a sense of calm the moment guests step onto the grounds. The patio invites lingering afternoons, whether lounging with a good book or enjoying a leisurely lunch prepared on the grill. As the day cools, the fire pit becomes a natural gathering placeperfect for roasting marshmallows, storytelling, or simply enjoying the crisp Southampton air. Total privacy and peaceful surroundings make the exterior feel like a private resort tucked away from the world. Stepping inside, guests are welcomed into a bright, open layout that flows effortlessly from room to room. The living area, with its comfortable seating and sun-filled atmosphere, sets the tone for relaxed living. It seamlessly transitions into the dining space, creating an easy environment for shared meals and family conversations. Adjacent lies the gourmet kitchen, thoughtfully equipped with top-of-the-line appliances, ample countertop space, and a coffee maker ready for early mornings or afternoon pick-me-ups. Large windows bring in abundant natural light, enhancing the homes welcoming energy. Modern conveniencesincluding reliable Wi-Fi, central AC, and a washer and dryerensure that comfort is never compromised. Every corner of the home has been designed for ease, warmth, and effortless enjoyment. The three bedrooms continue the homes theme of serenity and comfort. Each room features fresh linens, soft bedding, and calming dcor that invites restful nights and peaceful mornings. Whether its a primary suite offering a quiet escape or charming guest bedrooms ideal for families with children, every sleeping space is designed with relaxation in mind. The two bathrooms are modern, well-appointed, and stocked with plush towels and all the essentials needed for a seamless stay. A steam room adds a luxurious touch, offering a spa-like experience right at homeperfect for unwinding after a beach day or a morning jog along the bay. Despite its tucked-away tranquility, the home places guests close to the best of Southamptons vibrant coastal lifestyle. Renowned restaurants, boutique shops, and local art galleries are just minutes away, inviting exploration and discovery. Several golf courses provide opportunities for leisurely tee times, while nearby beaches promise sun-soaked days on the sand, gentle waves, and unforgettable sunsets. Whether guests seek family-friendly adventures, peaceful nature walks, or simply a quiet place to reconnect, this private Southampton Bullhead Bay escape offers an experience that feels both restorative and refineda sanctuary where every stay becomes a cherished memory. This property has a max occupancy of 6 Bedrooms Bedroom 1 - Primary: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Bedroom 3: One Double/Full Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2 - Hallway: Full Bath, First Floor/Main Floor, Shower TVs Bedroom 1 - Primary: Streaming Bedroom 2: Streaming Outdoors Grill (Gas), Patio Furniture (Chairs), Fence Around The Yard, Fire Pit (Wood-Burning), Deck/Patio Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Nespresso, Keurig), Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Den), Smart TV, Speaker System (Bluetooth Speaker), Steam Room, Private Entrance, Parking, Garage (Attached), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Privacy (Mostly Private) Location Nearby Beaches: Cooper’s Beach Flying Point Beach Halsey Neck Beach Cryder Beach Little Plains Beach Nearby Grocery Stores: Hank’s Farmstand Southampton Farmer’s Market Citarella Stop & Shop Nearby Restaurants and Bars: AM Southampton Southampton Social Club Claude’s Restaurant The Plaza Caf Southampton Social Club Union Cantina Union Burger Bar Sant Ambroeus 75 Main Tutto il Giorno Le Chef Other Location Information: Agawam Lake Park Shinnecock Hills Golf Club Other FAQ’s Backyard Fenced In: Yes Estimated Square Footage: 1,400 Suitability: Not handicap accessible. Not suitable for multiple families. Primary renter must be at least 30 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Stately Home with Jetted Tubs & Alfresco Dining; by Shops & Dining

Bridgehampton, NY, US
3 Bedrooms 7 Guests
Oct 9 - 11
$623 night

Please note that a reservation for this property needs to be approved before it is confirmed. Ocean Road Escape Beautifully Restored Barn, Open First Floor Plan, Historic Charm and Updates Furnishings, Close to Town and Ocean Beaches 4BR/3BA, Set on 1.5 Acres South of Highway & Across from Nature Preserve Old and new seamlessly converge at Ocean Road Escape, a four-bed, three-bath vacation home thats sure to delight up to eight guests. Located less than one mile from town on a one-and-a-half acre lot, the house is within walking distance of Bridgehampton antiques shops, art galleries, and upscale dining. Soaring ceilings and original wood beams characterize the beautifully renovated barn, where sunlight pours through generous floor-to-ceiling windows. Gather in the spacious living area with flat-screen TV, prepare a favorite recipe in the classic farmhouse kitchen, and enjoy home-cooked meals in the stately dining area. Drift to sleep in four comfortable bedrooms with queen-size beds, and wake each morning to refresh in three full bathrooms, including a marble master bath with luxurious jetted tub. The vast and secluded grounds were made for outdoor entertaining. Fire up the grill on the expansive blue-stone terrace, and dine al fresco beneath the shade of a patio umbrella. Go for a swim in the heated gunite pool, or recline in a poolside lounger with a captivating summer read. Famed Hampton beaches are a short drive away, while a 25-acre nature preserve is just across the street. *Pets are prohibited unless our express approval is provided *Pool use is at travelers own risk This property has a max occupancy of 7 Bedrooms Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Cable TV, Closet Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Closet Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Open Area Privacy Bathrooms Bathroom #1: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom #2: Full Bath, 2nd Floor, Shower Bathroom #3: Full Bath, 2nd Floor, Shower/Tub Combo TVs Bedroom 1: Cable Outdoors & Pool/Spas Deck/Patio (Uncovered), Grill (Gas), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Private Pool (Heated, Outdoor) Amenities Air Conditioning, Dryer, Heating, Internet (Wifi), Bed Linens, Washer, Hair Dryer, Living Room, Parking, Bath Towels, Essentials, Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Stove, Oven, Dishwasher, Microwave, Coffee (Pot, Nespresso), Toaster, Dishes and Silverware, Pots and Pans, Television (Main Living Room, Kitchen), Cable TV, Laptop-Friendly Workspace, Pots and Pans Suitability: Not handicap accessible. Primary renter must be at least 25 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

North Sea Gem

Southampton, NY, US
4 Bedrooms 12 Guests
Sep 14 - 17
$671 night

North Sea Gem Cozy Southampton Home with Private Pool, Outdoor Dining, Perfect for Families 4BR/3BA: private heated pool, outdoor dining and BBQ, multiple sitting areas, outdoor shower, total privacy, work-from-home space Nestled in the heart of the Hamptons, this cozy home in Southampton offers the perfect escape from the hustle and bustle of everyday life. Just minutes away from the charming villages of Southampton, Water Mill, and Sag Harbor, this delightful retreat boasts an open floor plan designed to enhance both relaxation and family togetherness. With four comfortable bedrooms and three well-appointed bathrooms, this home can comfortably accommodate up to six guests. The interior is spacious and bright, featuring multiple sitting and dining areas that invite you to unwind and savor each moment. Whether youre planning a family getaway or a reunion with friends, this property provides the ideal setting for making lasting memories. Located on a beautiful private block, the home offers an expansive patio complete with a BBQ and outdoor dining area, perfect for enjoying meals al fresco amidst the serene surroundings. The exterior amenities of this Southampton gem are truly exceptional, providing total privacy and a host of options for outdoor enjoyment. The private heated pool is a standout feature, offering a luxurious spot for swimming and sunbathing. Surrounding the pool is an expansive patio, where youll find a large dining table ideal for family meals or evening gatherings. Multiple sitting areas are strategically placed throughout the patio, making them perfect for sipping cocktails and engaging in leisurely conversations. The BBQ area is well-equipped for grilling up your favorite dishes, adding to the delightful outdoor living experience. There is plenty of free parking available, ensuring convenience for all guests. The expansive yard offers ample space for outdoor activities, while the outdoor shower adds a touch of practicality and luxury, allowing you to rinse off after a day at the beach or by the pool. Step inside this inviting home, and youll immediately be captivated by its open layout and abundance of natural light. The living spaces flow effortlessly from one area to the next, creating a harmonious environment that encourages relaxation and connection. High-speed WiFi ensures you stay connected no matter the amount of devices. Central air conditioning keeps the home cool and comfortable, no matter the season. The living room, with its plush seating and cozy atmosphere, leads seamlessly into the dining room and the gourmet kitchen. The kitchen is a chefs delight, featuring top-of-the-line appliances and a coffee maker to start your mornings right. For those who need to balance work with leisure, a dedicated work-from-home space is available. Throughout the home, multiple sitting and dining areas provide ample options for lounging, dining, and entertaining. The bedrooms in this Southampton retreat are designed with comfort and tranquility in mind. Each room is outfitted with fresh linens and all the essentials you need for a restful stay. The master bedroom features a luxurious bed and ample storage space, while the additional bedrooms offer cozy accommodations for guests. The bathrooms are modern and well-appointed, stocked with plush towels and high-quality toiletries to enhance your stay. This charming Southampton home is ideally located close to an array of attractions. The nearby villages of Southampton, Water Mill, Bridgehampton, and Sag Harbor offer a wealth of dining options, from casual eateries to fine dining restaurants. Explore art galleries showcasing local and international talent, or browse the unique shops and boutiques for that perfect souvenir. Golf enthusiasts will appreciate the proximity to several top-rated golf courses, while beach lovers can easily access some of the Hamptons most beautiful beaches. Whether youre seeking relaxation or adventure, this delightful home serves as the perfect base for exploring all that the Hamptons have to offer. This property has a max occupancy of 12 Bedrooms Primary Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Closet Bedroom 4: One Queen Bed, Lower Level, Air Conditioning, TV Common Room: One Sleep Sofa, First Floor/Main Floor, Air Conditioning Lower Level Common Room: One Sleep Sofa, Lower Level, TV Bathrooms Primary Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower Bathroom 3: Full Bath, Lower Level, Shower TVs Primary Bedroom 1: Streaming Bedroom 4 Lower Level Common Room Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas, Charcoal), Outdoor Shower (Hot + Cold Water), Fire Pit (Wood-Burning, Gas), Bicycle, Beach Chairs, Cooler, Kayak/Canoe, Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Ice Maker, Coffee (Pot), Toaster, Private Entrance, Parking, Smoke Detector, Essentials, Hair Dryer, Usable Fireplace (Wood-Burning), Television (Main Living Room), Smart TV, Speaker System (Stereo), Carbon Monoxide Detector, Fire Extinguisher Special Features Neighborhood villa Neighborhood marina with 3 kayaks for use Location Nearby Beaches: Cooper’s Beach Flying Point Beach Halsey Neck Beach Cryder Beach Little Plains Beach Nearby Grocery Stores: Hank’s Farmstand Southampton Farmer’s Market Citarella Stop & Shop Nearby Restaurants and Bars: AM Southampton Southampton Social Club Claude’s Restaurant The Plaza Caf Southampton Social Club Union Cantina Union Burger Bar Sant Ambroeus 75 Main Tutto il Giorno Le Chef Other Location Information: Agawam Lake Park Shinnecock Hills Golf Club Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 2,500 Rental Registration: 241868 expires on 11/26/2026. Suitability: Not handicap accessible. Primary renter must be at least 28 years old. Pet Policy: One dog of 50 lbs or less is permitted for an additional $150.00 per booking. Dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. Guest shall be responsible for the costs associated with excessive usage of utilities during the term of the Reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Old Trail Tranquility

Water Mill, NY, US
5 Bedrooms 12 Guests
Sep 11 - 14
$956 night

Old Trail Tranquility Beautiful Contemporary Water Mill Home Centrally Located with Private Pool 5BR + office/4BA: centrally located, private pool, spa, gas BBQ, outdoor dining area, multiple sitting areas, outdoor shower, finished lower level Nestled on a serene private block in the heart of the Hamptons, this contemporary 5-bedroom Water Mill home offers the perfect escape from daily life. Centrally located between the charming hamlets of Water Mill, Sag Harbor, and Southampton, this thoughtfully appointed sanctuary accommodates families and groups in style, offering an additional sleeping space within a quiet home office. As you step inside, you are welcomed by an open layout that basks in an abundance of natural light, creating an atmosphere of tranquility and relaxation. The open living spaces, consisting of the living room, dining room, and kitchen, are seamlessly interconnected, promoting easy socializing and entertainment. Every corner of the home has been designed with your comfort in mind. The fully equipped kitchen boasts top-of-the-line appliances, offering a culinary playground for cooking enthusiasts. Adjacent to the kitchen, the stylish living room features a cozy fireplace and a big-screen TV, perfect for a family movie night or a lazy Sunday afternoon. A wall of windows and glass doors offers a glimpse of the paradise that awaits outside while allowing easy access to the back deck. Descend to the finished lower level, where you’ll discover a spacious media area, perfect for hosting game nights or simply unwinding. The adjacent home office offers an ideal space for those who need to catch up on work, plus it doubles as an extra sleeping area, perfect for overnight guests or family members seeking a quiet retreat. Step outside to your personal oasis where nature, comfort, and privacy converge. An expansive deck, complete with a dining table and gas BBQ, invites you to alfresco dinners under the stars. Multiple sitting areas dispersed throughout the property offer cozy corners for sipping cocktails or curling up with a good book. At the heart of this outdoor retreat, a shimmering pool and hot tub await, providing a refreshing escape on hot summer days, while an outdoor shower adds a touch of luxury. Inside, the five comfortable bedrooms have been designed with restful nights in mind. Each is dressed with fresh, high-quality linens and features tasteful dcor that reflects the home’s serene surroundings. On the second floor, you’ll find the Master suite offering the ultimate in privacy, with an ensuite bath with a large shower, and a soaking tub. The master bedroom opens onto an outdoor deck, a perfect place to enjoy your morning coffee. The remaining four bathrooms are stocked with all the essentials you need, promising a hassle-free stay. Its unbeatable location places this home just a short drive from some of the Hamptons’ most beautiful beaches, providing endless opportunities for sunbathing, swimming, or taking leisurely seaside strolls. Moreover, its central position between Southampton and Watermill offers easy access to a plethora of world-class restaurants, trendy shopping spots, esteemed art galleries, and top-tier golf courses. In essence, this beautiful Water Mill property is more than just a vacation rental; it’s your home away from home in the Hamptons, offering an unforgettable experience that beautifully combines the tranquility of a secluded retreat with the convenience of a central location. Come, experience it for yourself. This property has a max occupancy of 12 Bedrooms Primary Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet, Balcony/Deck Guest Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Guest Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Guest Bedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Standard Closet Guest Bedroom 5: One Queen Bed, Lower Level, Air Conditioning, Closet Office: One Sleep Sofa, Lower Level, Air Conditioning, TV, Standard Closet, Privacy Bathrooms Primary Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, Tub 1st Floor Shared Bathroom 2: Full Bath, First Floor/Main Floor, Shower Guest Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Lower Level Hallway Bathroom 4: Full Bath, Lower Level, Shower/Tub Combo TVs Primary Bedroom 1 Office Outdoors & Pool/Spas Balcony, Deck/Patio (Uncovered), Grill (Gas), Beach Chairs (3 Chairs), Outdoor Shower (Hot + Cold Water), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Cooler, Swing Set, Hot Tub (Freestanding Hot Tub), Private Pool (Heated, Outdoor, Saltwater) Amenities Bed Linens, Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Game Room, Garage, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Nespresso, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Blender, Speaker System (Bluetooth Speaker, Sonos), Television (Main Living Room, Den, Office), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Essentials, Smart TV, Ice Maker, Laptop-Friendly Workspace Suitability: Not handicap accessible. Primary renter must be at least 27 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Hot Tub is available year-round. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Southampton Paradise

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 11 - 18
$1,520 night

Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Paradise Chic Southampton Getaway with Heated Pool & Seamless Indoor-Outdoor Living 4BR/3BA: Private heated pool, plush chaise loungers, outdoor sofa, al-fresco dining & gas BBQ Tucked away on a quiet street in Southampton, this chic and stylish single-story home is the ultimate retreat for travelers seeking comfort, sophistication, and effortless indoor-outdoor living. With four spacious bedrooms and three full bathrooms, this bright and airy residence comfortably accommodates up to eight guests, making it perfect for families, couples, or groups of friends looking to escape the everyday and indulge in a quintessential Hamptons beach vacation. Thoughtfully designed with curated modern furnishings and an open-concept layout, the home exudes relaxed elegance from the moment you arrive. Step into the private backyard and discover a secluded resort-style oasis, surrounded by lush greenery and mature landscaping that offers both beauty and privacy. The fenced-in yard is a true highlight of the property, featuring a sparkling heated pool, expansive sundeck lined with plush chaise loungers, and multiple serene seating areas ideal for soaking up the sun or savoring a cocktail at golden hour. The wooden deck is outfitted with a dining table, stylish chairs, and a plush outdoor sofaperfect for al fresco dinners and late-night conversations under the stars. A top-of-the-line gas BBQ invites guests to grill up fresh finds from nearby farm stands, and ample off-street parking adds ease to every arrival and departure. Inside, the home is bathed in natural light thanks to the large sliding glass doors that open directly onto the deck, creating a seamless flow between the indoor and outdoor living spaces. The soaring ceilings with exposed wood beams lend warmth and character to the interiors, while the open layout encourages connectionwhether you’re preparing meals in the chefs kitchen, sharing a leisurely breakfast around the dining table, or unwinding in the spacious living room. Modern finishes, tasteful dcor, and high-end amenities elevate every detail. The kitchen comes fully stocked with top-tier appliances, cookware, dishes, and everything needed to entertain or dine at home. In the living area, guests can enjoy a cozy fireplace, stylish furnishings, a flat-screen TV, and tranquil views of the backyard. The sleeping quarters are equally inviting. All four bedrooms are situated on the main level, thoughtfully arranged for ease and comfort. The serene primary suite features a plush king-sized bed, direct access to the backyard, and a spa-inspired en suite bathroom complete with a walk-in shower and contemporary finishes. A second guest suite offers a comfortable queen bed and private en suite bath with a walk-in shower, ideal for visitors seeking a bit more privacy. The remaining two guest roomsone outfitted with two twin beds, the other with a queenshare a beautifully appointed hall bathroom with a tub/shower combination. Each bedroom is designed with comfort in mind, offering fresh linens, modern furnishings, and all the essentials for a restful nights sleep. This thoughtfully curated home is equipped with everything guests need for a seamless stay: air conditioning, high-speed WiFi, washer and dryer, a dedicated workspace for remote work, and all the modern conveniences to ensure your stay is as effortless as it is memorable. When its time to explore, youre just minutes away from the best of Southampton. Spend the day at nearby Coopers Beach or Gin Lane Beach, both known for their wide stretches of sand and rolling dunes. Southamptons charming village center is just a short drive or bike ride away, where youll find boutique shops, designer stores, gourmet markets, and renowned restaurants serving everything from casual seafood to upscale fare. Art lovers can browse the local galleries or visit the Parrish Art Museum for a taste of culture. Outdoor enthusiasts will enjoy nearby parks and nature preserves, while wine lovers can spend the afternoon exploring local wineries and tasting rooms just a short drive from town. The area is also home to several seasonal farm stands, perfect for picking up fresh produce, baked goods, and flowers to enjoy back at the house. Whether you’re lounging poolside with a book, hosting a sunset dinner on the deck, or strolling the beaches at sunrise, this Southampton escape promises a luxurious, relaxing, and unforgettable Hamptons experience. This property has a max occupancy of 8 Bedrooms Bedroom 1 - Primary: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Twin Beds: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, Streaming TV Bedroom 3 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Bedroom 4 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2 - Guest: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 3 - Bedroom 4 Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower TVs Bedroom 1 - Primary: Streaming Bedroom 2 - Twin Beds: Streaming Bedroom 3 - Guest: Streaming Bedroom 4 - Guest: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Grill (Gas), Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Private Pool (Heated, Outdoor, Freshwater) Amenities Bed Linens, Usable Fireplace (Gas-Burning), Air Conditioning (Central Air), Heating, Internet (Wifi), Hair Dryer, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Nespresso, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Smart TV, Laptop-Friendly Workspace, Washer, Dryer, Essentials Location Nearby Beaches: Cooper’s Beach Flying Point Beach Halsey Neck Beach Cryder Beach Little Plains Beach Nearby Grocery Stores: Hank’s Farmstand Southampton Farmer’s Market Citarella Stop & Shop Nearby Restaurants and Bars: AM Southampton Southampton Social Club Claude’s Restaurant The Plaza Caf Southampton Social Club Union Cantina Union Burger Bar Sant Ambroeus 75 Main Tutto il Giorno Le Chef Other Location Information: Agawam Lake Park Shinnecock Hills Golf Club Suitability: Primary renter must be at least 30 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $70.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

The Southampton Grand

Southampton, NY, US
6 Bedrooms 12 Guests
Sep 15 - 17
$3,172 night

Please note that a reservation for this property needs to be approved before it is confirmed. The Southampton Grand Luxurious Southampton Retreat with Private Pool and Pool House, Great for Families 6BR/7.5BA: Private heated pool, pool house, fenced in yard, outdoor dining, gas BBQ, and firepit Nestled on a quiet street in the heart of Southampton, this elegant six-bedroom, seven-and-a-half-bathroom home offers the perfect escape from the hustle of daily life. Centrally located near Southampton’s vibrant town center, pristine beaches, and renowned dining establishments, the property is designed to provide an exceptional blend of comfort, privacy, and luxury. Thoughtfully designed with sophisticated travelers in mind, this home offers a warm and inviting atmosphere, making it ideal for families and groups seeking a high-end retreat. Upon arrival, guests are welcomed by a beautifully manicured, fenced-in yard that ensures privacy and seclusion. The centerpiece of the outdoor space is the private, heated pool, perfect for refreshing morning swims or lounging in the afternoon sun. The adjacent pool house adds to the charm, featuring a stylish living area and a full bathroom, creating a comfortable extension of the main home. The sun deck is outfitted with multiple sitting areas, ideal for morning coffee or evening cocktails. Al fresco dining is a breeze with the gas BBQ and outdoor dining table, while the built-in fire pit creates a cozy setting for gathering under the stars. Multiple seating areas throughout the outdoor space offer options for both relaxation and conversation, ensuring every guest finds their perfect spot. With plenty of free parking, hosting friends and family is effortless. Inside, the homes traditional layout offers a seamless blend of elegance and comfort. The formal living room features a plush sofa, a large flat-screen TV, and a fireplace that serves as a cozy focal point for cool evenings. Adjacent to the living room, the formal dining room provides ample space for hosting memorable meals. The large, luxurious central kitchen is a chefs dream, fully equipped with top-of-the-line appliances, a coffee maker, and all the cooking essentials needed to prepare gourmet meals. The expansive island with seating makes it easy to gather while cooking or enjoying drinks. Coffered ceilings add a refined touch to the kitchens design, while sliding doors open directly to the pool, creating a fluid connection between indoor and outdoor living spaces. A fully finished basement offers additional living space, perfect for movie nights or a quiet retreat. For those needing to stay connected, a dedicated work-from-home space and high-speed Wi-Fi are available. The sleeping accommodations are thoughtfully arranged to provide privacy and comfort for every guest. The primary suite, located on the second floor, is a luxurious retreat with a king-sized bed, a private balcony overlooking the property, and a spacious ensuite bathroom with a soaking tub, walk-in shower, and dual vanities. Five of the six bedrooms feature ensuite bathrooms, ensuring that every guest enjoys a private and comfortable stay. A first-floor guest room with an ensuite bath provides easy access and convenience. The second floor includes three additional guest rooms, each tastefully decorated and furnished with premium bedding and fresh linens. An additional guest room with an ensuite bath is located in the basement, offering extra privacy and comfort. With seven and a half bathrooms, every guest has ample space to refresh and unwind. The home is located just minutes from a range of local attractions. Southamptons charming village center is home to an array of upscale boutiques, art galleries, and local markets. A variety of renowned restaurants offer everything from fresh seafood to gourmet cuisine, making dining out an experience in itself. The propertys proximity to Southamptons iconic beaches ensures that a day by the ocean is always within reach. Spend the afternoon exploring nearby wineries or playing a round of golf at one of the areas prestigious courses. For those seeking culture, the Parrish Art Museum and other local galleries provide a glimpse into the vibrant artistic community of the Hamptons. This Southampton retreat combines the best of luxury, comfort, and convenience, offering guests an exceptional vacation experience. Whether youre lounging by the pool, gathering around the fire pit, or exploring the vibrant local scene, this home promises a relaxing and unforgettable escape. This property has a max occupancy of 12 Bedrooms Bedroom 1 - First Floor Guest: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Second Floor Guest: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Standard Closet Bedroom 3 - Second Floor Guest: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV Bedroom 4 - Second Floor Guest: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 5 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 6 - Basement Guest: One King Bed, Lower Level, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bathrooms Bathroom 1 - First Floor Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower First Floor Powder Room: Half Bath, First Floor/Main Floor Bathroom 2 - Guest Ensuite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4 - Second Floor Hallway: Full Bath, 2nd Floor, Shower Bathroom 3 - Guest Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 5 - Primary Ensuite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 6 - Basement Ensuite: Full Bath, Lower Level, Ensuite, Shower Bathroom 7 - Pool House Bathroom: Full Bath, Pool House First Floor/Main Floor, Shower TVs Bedroom 1 - First Floor Guest: Streaming Bedroom 2 - Second Floor Guest Bedroom 3 - Second Floor Guest: Streaming Bedroom 4 - Second Floor Guest: Streaming Bedroom 5 - Primary: Streaming Bedroom 6 - Basement Guest: Streaming Outdoors & Pool/Spas Balcony, Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Grill (Gas), Fire Pit (Gas), Private Pool (Heated, Outdoor, Freshwater) Amenities Bed Linens, Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Garage, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Blender, Television (Main Living Room, Additional Structure (Pool House, guest house, detached garage)), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Smart TV, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Essentials Location Nearby Beaches: Cooper’s Beach Flying Point Beach Halsey Neck Beach Cryder Beach Little Plains Beach Nearby Grocery Stores: Hank’s Farmstand Southampton Farmer’s Market Citarella Stop & Shop Nearby Restaurants and Bars: AM Southampton Southampton Social Club Claude’s Restaurant The Plaza Caf Southampton Social Club Union Cantina Union Burger Bar Sant Ambroeus 75 Main Tutto il Giorno Le Chef Other Location Information: Agawam Lake Park Shinnecock Hills Golf Club Other FAQ’s Pool Fenced In: No Backyard Fenced In: No Estimated Square Footage: 5,000 Suitability: Primary renter must be at least 30 years old. Pet Policy: One dog of 50 lbs or less is permitted for an additional $250.00 per booking. Dogs over 50 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: A refundable cash security deposit of $5,000 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Four-Acre Estate with Pool, Hot Tub, Games, Tennis & Gym; by Beach

Sagaponack, NY, US
7 Bedrooms 10 Guests
Sep 15 - 23
$4,224 night

Sagaponack Compound On Four Acres, In the Heart of Sagaponack, Gourmet Eat-In Kitchen, Tennis Court, Orchard, Near Sagg Main Beach 7BR/8BA w/Gourmet Kitchen, Family Room, Pool, Spa, Tennis Court, Pool House, Patio Escape to a stay of luxury and nourishment of the soul at this custom built compound on four acres of land, overlooking 25 acres of agricultural reserve in the heart of Sagaponack. While everything one would need for an unforgettable getaway is available at the home, the Sagg Main beach is just over a mile away. Inside the main house, guests, in particular those who love to cook, will be in awe of the large, open gourmet eat-in kitchen with island and plenty of seating for a big breakfast or hang out over a cup of coffee. Whip up a family-style meal to share in the formal dining room. Take a load off in the family room, including a fireplace and TV, and stay entertained in the homes media room and library. Additional space to spend quality time with one another includes the den with desk and couch. The tremendous back of the house offers plenty of space for relaxing, bonding with friends and family, and playing. Before floating around in the 60 foot pool and spa, partake in a friendly game of tennis on the homes private court. Grill some steaks on the back patio with grill. A separate pool house contains a kitchenette and additional living space. Let nature in with the specimen gardens, open lawns, orchard and stunning Hamptons views. Seven bedrooms, including a master bedroom and eight baths complete this grand estate. Please note that the Pool House will not be available October-April. This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 2: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, TV, Walk-in Closet, Balcony/Deck Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 4: One Double/Full Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Walk-in Closet Bedroom 5: One Double/Full Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet Bedroom 6: One Double/Full Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom Bedroom 7: Two Bunk Beds, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, TV Additional Sleeping Space 1: One Double/Full Bed, Pool House 2nd Floor, Privacy Additional Sleeping Space 2: One King Bed, Pool House 2nd Floor, Privacy Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 6: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 7: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 8: Half Bath, First Floor/Main Floor Bathroom 9: Half Bath, First Floor/Main Floor Bathroom 10: Full Bath, Pool House First Floor/Main Floor, Shower Bathroom 11: Full Bath, Pool House 2nd Floor, Shower TVs Bedroom 2 Bedroom 7 Outdoors & Pool/Spas Beach Chairs (2 Chairs), Outdoor Shower, Lounge Chairs (6 Chairs), Deck/Patio, Balcony, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Private), Tennis Equipment (Rackets), Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning (Central Air), Heating, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Usable Fireplace (Wood-Burning), Internet (Wifi), Microwave, Coffee (Nespresso, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Gym/Fitness Room (Elliptical, Weight Training Equipment), Game Room, Ping Pong Table, Speaker System (Sonos), Television, Private Entrance, Steam Room, Parking (4 Cars In Driveway), Living Room, Kitchen, Carbon Monoxide Detector, Smoke Detector, Essentials, Hot Water, Refrigerator, Oven, Wine Fridge, Cable TV, Smart TV, Laptop-Friendly Workspace, Pots and Pans, Stove, Ice Maker, Dishwasher Other FAQ’s Estimated Square Footage: 9,900 Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $200.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: A refundable cash security deposit of $10,000 is required for this property. Information with respect to the payment and administration of the security deposit is governed by a separate Security Deposit Agreement between owner and guest, that shall be signed by both parties prior to check-in. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Stately, Upscale Home with Stunning Pool Deck & Amazing View

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 11 - 14
$875 night

Little Peconic Bayview Southampton Luxury Estate with Pool, Sunset Bay Views & Resort-Style Backyard 5BD/5BA: Private heated pool, luxurious gazebo, expansive sundeck, primary suite with balcony, grand designer interiors, and chef's kitchen Tucked behind a gated entrance and framed by lush, mature landscaping, and at one of the highest elevations in Southampton, this luxurious estate invites guests into a serene world of refined elegance and resort-style comfort. Perfectly situated just minutes from the heart of town, this spacious five-bedroom, five-bathroom home comfortably accommodates up to ten guests and offers the perfect retreat for families or groups looking to unwind, reconnect, and savor the beauty of the Hamptons. From the moment you arrive, the sweeping sunset views over Little Peconic Bay and the sense of total privacy make it clear: youve arrived somewhere truly special. Step outside and discover a backyard that rivals the most exclusive resorts. Enveloped by vibrant greenery, the expansive outdoor space is designed for both relaxation and entertainment. A private, heated pool sits at the center, surrounded by a generous sundeck lined with plush chaise loungersperfect for lazy afternoons in the sun or an evening swim under the stars. The covered gazebo, complete with overhead fans, lighting, and plush lounge seating, offers an ideal space for afternoon cocktails or a quiet moment with a book. Adjacent to this, an alfresco dining area invites open-air meals beneath the sky, with a gas BBQ at the ready for summer grilling. Multiple outdoor seating areas provide cozy corners for coffee at sunrise or a glass of ros at dusk. With ample on-site parking and total seclusion, this outdoor oasis sets the tone for an unforgettable stay. Inside, the home is a masterclass in modern Hamptons luxury. Grand in scale and rich in natural light, the main level features soaring double-height ceilings and floor-to-ceiling windows and sliding doors that blur the lines between indoor and outdoor living. The open-concept layout allows guests to move effortlessly from the spacious living roomcomplete with designer furnishings and serene viewsto the formal dining area that comfortably seats eight. At the heart of the home is a large chefs kitchen, equipped with top-of-the-line appliances, generous counter space, and a large island that serves as both a prep area and gathering spot. Whether you’re planning a casual breakfast or an elegant dinner party, the space offers everything needed to entertain with ease and style. Each of the five bedrooms is designed with comfort and tranquility in mind. On the second floor, the Primary Suite offers a private sanctuary, featuring a king-size bed, a spa-like ensuite bathroom with a walk-in shower and soaking tub, and a private balcony that overlooks the pool and bayan idyllic place to begin or end each day. On the main floor, two additional guest bedrooms provide convenient, private accommodations: one with a king bed and ensuite bathroom with a walk-in shower, and another with a queen bed, sliding doors that lead directly to the pool area, and an ensuite bath with a tub/shower combination. Upstairs, two more guest roomsone with a queen bed and the other with two twin bedsshare a Jack and Jill bathroom with a walk-in shower. For larger groups or those seeking additional privacy, the lower level includes a bonus sleeping area with its own full bathroom featuring a walk-in shower. Throughout the home, guests will find fresh linens, hotel-quality bedding, and all the essentials needed for a seamless and restful stay. Beyond the gates of this private estate, guests are just a short drive from the very best of Southampton. Spend the day browsing the boutique shops, art galleries, and cafes that line Main Street, or enjoy a decadent meal at one of the areas renowned restaurants. Ocean beaches and bayfront parks are easily accessible for sunbathing, swimming, or a scenic walk along the shore. From cultural attractions like the Southampton Arts Center to local farmers markets, golf courses, and wellness spas, everything that makes the Hamptons such a desirable destination is within easy reach. Whether you’re gathering with family for a week by the sea or reconnecting with friends for a summer celebration, this luxurious estate offers the space, privacy, and elevated experience you seek. Elegant yet relaxed, spacious yet warm, it’s the perfect setting for making timeless memories in one of the Hamptons most iconic locations. This property has a max occupancy of 10 Bedrooms Bedroom 1 - Guest: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet, Balcony/Deck Bedroom 2 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Balcony/Deck Bedroom 3 - Guest: One Queen Bed, 2nd Floor, Air Conditioning, Closet Bedroom 4 - Guest: Two Twin Single Beds, 2nd Floor, Air Conditioning, Closet Bedroom 5 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Walk-in Closet, Balcony/Deck Additional Sleeping Space: One King Bed, Lower Level, Air Conditioning, Ensuite Bathroom, Privacy Bathrooms Bathroom 1 - Guest Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 3: Full Bath, 2nd Floor, Jack & Jill, Shower/Tub Combo Bathroom 4 - Primary: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5 - Lower Level: Full Bath, Lower Level, Shower TVs Bedroom 1 - Guest Bedroom 5 - Primary Outdoors & Pool/Spas Beach Chairs, Beach Umbrella, Lounge Chairs (4 Chairs), Deck/Patio, Balcony, Patio Furniture (Table, Chairs, Umbrella), Bicycle (1 Adult Bikes), Grill (Charcoal), Cooler, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Air Conditioning, Heating, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Internet (Wifi), Microwave, Coffee (Nespresso, Other), Dishes and Silverware, Pots and Pans, Toaster, Speaker System (Bluetooth Speaker, Sonos, Stereo), Television, Private Entrance, Parking (8 Cars In Driveway), Garage (2 Cars In Garage), Living Room, Kitchen, Smoke Detector, Essentials, Carbon Monoxide Detector, Hot Water, Refrigerator, Blender, Stove, Oven, Dishwasher, Laptop-Friendly Workspace, Pots and Pans Special Features The residence is perched at one of the highest elevations in Southampton, which gives the property amazing sunset bay / water views. High Cathedral ceilings. Open floor plan. Gazebo Brick patio Location Nearby Beaches: Flying Point Beach Sagg Main Beach Coopers Beach Cryder Beach Nearby Grocery Stores: King Kullen Cromer Citarella North Sea Farm Halsey Farm & Nursery Nearby Restaurants and Bars: Tutto il Giorno Bilbouquet Pierre Sant’Ambreaus Pellegrino Almond Walfer Estate Vineyard Other Location Information: Close to the Marina Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 4,700 Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Peconic Hills Modern

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 11 - 14
$1,484 night

Peconic Hills Modern Brand New Southampton Home with Modern Design, Private Heated Pool, Open Floor Plan, Perfect for Families 5BR/5.5BA: private heated pool, outdoor dining and gas BBQ, brand new, modern design, work-from-home space, multiple sitting areas Step into a world of contemporary luxury with this brand new construction in Southampton. Boasting a modern design that complements its serene surroundings, this exquisite property is just minutes away from Southampton, Sag Harbor, and Water Mill. With five bedrooms and five-and-a-half bathrooms, this home can comfortably accommodate up to 10 guests, making it an ideal retreat for families or large groups seeking an escape from daily life. Positioned on a beautifully private block, the house shines with multiple sitting and dining areas, all designed with space and brightness in mind. The outdoor amenities of this estate are designed to offer total privacy and relaxation. An expansive yard surrounds a patio equipped with outdoor dining facilities and a gas BBQ, perfect for enjoying meals under the open sky. Steps away, a brand new heated pool invites guests to unwind, while various sitting areas provide a perfect setting for evening cocktails. The convenience of plenty of free parking adds to the ease and comfort of your stay. Inside, the home greets you with an open layout bathed in natural light, creating a warm and inviting atmosphere. The central air conditioning and complimentary WiFi ensure comfort and connectivity throughout your stay. The living areas flow effortlessly from a cozy living room with a fireplace to a dining room and onto a gourmet island kitchen equipped with a coffee maker and top-of-the-line appliances. For those who need to balance leisure with work, a dedicated workspace is thoughtfully included. The finished lower level features an additional media area, offering extra space for entertainment and relaxation. Each bedroom in this splendid home is a private oasis, complete with fresh linens and all the essential amenities to ensure a restful night’s sleep. The bathrooms are equally luxurious, stocked with necessities that cater to your every need and comfort. This remarkable property is conveniently located close to the cultural hubs of Sag Harbor, Southampton, and Water Mill, with North Sea Beach just a short drive away. Whether you’re looking to explore the local galleries, enjoy fine dining, or simply relax by the sea, this Southampton retreat offers the perfect base for a memorable vacation. Experience the blend of modern luxury and inviting charm in this exceptional Southampton home. This property has a max occupancy of 10 Bedrooms Primary Bedroom 1: One King Bed, 3rd Floor, Air Conditioning, Full Ensuite Bathroom, Cable Streaming TV, Standard Closet, Balcony/Deck Bedroom 2: One King Bed, 3rd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 3: One Queen Bed, 3rd Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 4: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 5: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bathrooms Powder Room 1: Half Bath, First Floor/Main Floor Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Handicap Accessible, Jack & Jill, Shower Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4: Full Bath, 3rd Floor, Ensuite, Jack & Jill, Shower/Tub Combo Primary Bathroom 5: Full Bath, 3rd Floor, Ensuite, Shower Bathroom 6: Full Bath, 3rd Floor, Ensuite, Shower TVs Primary Bedroom 1: Cable and Streaming Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 4: Streaming Bedroom 5: Streaming Outdoors & Pool/Spas Deck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fence Around The Yard, Fence Around The Pool, Fire Pit (Gas), Private Pool (Outdoor, Heated, Saltwater) Amenities Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Television (Main Living Room, Kitchen), Speaker System (Bluetooth Speaker), Parking, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Bed Linens, Bath Towels, Pool/Beach Towels, Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Essentials, Iron/Ironing Board, Coffee (Pot), Cable TV, Smart TV, Private Entrance, Hair Dryer, Privacy (Mostly Private) Special Features Private community- Southampton Acres. Short distance to Peconic Bay and Deeded private Beach Rights. House sits on 1 full acre. Location Nearby Beaches: Private beach access and right of way just 5 mins from house. Nearby Grocery Stores: Porcos General Store Cromers General Store Nearby Restaurants and Bars: Pellegrinos Dowlings Bell and Anchor Cappelletti Restaurant & Take Out Captain Jacks On The coast Boa Thai Asian Fusion Other Location Information: Just 10 minutes away from the beautiful Southampton Village and 10 minutes away from the beautiful village of Sag Harbor. Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 4,400 Suitability: Not handicap accessible. Primary renter must be at least 35 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $135.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Peconic Hills Hideaway

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 16 - 18
$610 night

Peconic Hills Hideaway Newly Renovated Southampton Oasis with Private Pool, Indoor-Outdoor Living, & Chic Interiors 4BR/3BA: Heated pool, expansive sundeck, open floor plan, modern kitchen, den with TV, private 1-acre yard, ideal for families or groups Tucked away on a quiet street in Southampton, this newly renovated four-bedroom, three-bathroom modern retreat offers the perfect blend of coastal elegance and effortless comfort. Ideal for families or small groups, the home is nestled on a full acre of private, fenced-in landan idyllic setting for those looking to unwind and savor the relaxed pace of life in the Hamptons. The interior is light, bright, and impeccably styled, with curated modern furnishings that add an air of sophistication to every space. And with its prime central location, you’re just minutes from Southampton Village’s charming shops, gourmet restaurants, and world-renowned beachesyet the peaceful, secluded atmosphere of this home makes it feel worlds away from it all. The exterior spaces are designed to elevate your outdoor living experience. Begin your days sipping coffee from the cozy outdoor sofa on the back deck, surrounded by mature trees that create a true sense of privacy. The expansive wooden sundeck wraps around a beautiful private heated pool, complete with chaise loungers for soaking in the sun. An inviting outdoor dining area, gas BBQ, and outdoor pizza oven set the stage for unforgettable al fresco evenings, whether you’re crafting homemade pizzas with the family or gathering for leisurely dinners under the stars. An outdoor shower with both hot and cold water makes it easy to transition from beach days to backyard entertaining. Whether youre planning a weekend of poolside relaxation or afternoon cocktails under the sky, the backyard is a personal oasis thats perfect for entertaining, lounging, or simply escaping the demands of everyday life. With ample parking and a peaceful setting, this home is a true Hamptons hideaway. Step inside and youll be welcomed by a bright, open-concept layout filled with natural light. The seamless flow between the living room, kitchen, and dining areas makes this home ideal for gathering and entertaining. Large sliding glass doors open wide to the back deck, creating a harmonious blend of indoor and outdoor living. The living room is anchored by a sleek fireplace and outfitted with plush, stylish seatingperfect for relaxing after a beach day or cozying up in the evenings. For more casual downtime, a separate den offers a large-screen TV, making it the ideal space for movie nights or catching the big game. The dining area sits adjacent to the kitchen and comfortably seats a full group for shared meals and conversation. Guests looking to maintain their wellness routine while away will appreciate the Bowflex adjustable weights, offering the convenience of an at-home workout whenever inspiration strikes. The heart of the homethe kitchenhas been fully updated with high-end appliances, a wine fridge, and a generous island that doubles as both a prep space and casual gathering spot. Whether youre planning to cook up fresh finds from local farm stands, host a pizza night using the outdoor oven, or bring in a private chef for a special evening, this kitchen is designed to elevate your culinary experience. Each of the four bedrooms is thoughtfully appointed with fresh linens, serene dcor, and all the essentials for a restful stay. The spacious primary suite features a luxurious king bed, direct access to the backyard, and a spa-inspired en suite bathroom complete with a soaking tub and a large walk-in showeryour own private sanctuary. The additional three guest bedrooms each feature comfortable queen beds and share two stylish hall bathroomsone with a walk-in shower and the other with a tub/shower comboensuring comfort and convenience for all guests. When youre ready to explore beyond the property, youll find that the best of Southampton is just minutes away. Spend the day browsing the boutiques and art galleries along Main Street, or enjoy a leisurely lunch at one of the many acclaimed restaurants in town. White sand beaches like Coopers Beach and Flying Point Beach are a quick drive away, offering breathtaking ocean views and the perfect setting for sunbathing or swimming. For those looking to explore the area at a slower pace, two adult bicycles and a Woom children’s bike provide a fun and convenient way to enjoy the surrounding neighborhoods and scenic streets. Nearby farm stands and local wineries offer fresh produce and seasonal finds, while beautiful parks and scenic trails invite outdoor adventures. Whether youre in the mood for a day at the beach, a family bike ride, a round of golf, or a wine tasting tour, everything is within easy reach. Combining modern comfort with Hamptons charm, this chic Southampton home invites you to slow down, reconnect, and make lasting summer memories. From the curated interiors to the tranquil outdoor living spaces, every detail has been designed to help you relax, unwind, and experience the very best of coastal living. This property has a max occupancy of 8 Bedrooms Bedroom 1 primary: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Bedroom 3: One King Bed, First Floor/Main Floor, Air Conditioning, Standard Closet 4 Guest bedroom: One King Bed, First Floor/Main Floor, Air Conditioning, Standard Closet, Balcony/Deck Bathrooms Bathroom 1 primary: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, First Floor/Main Floor, Shower, Tub Bathroom 3: Full Bath, First Floor/Main Floor, Shower TVs Bedroom 1 primary: Streaming Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs), Grill (Gas), Outdoor Shower (Hot + Cold Water), Beach Chairs (6 Chairs), Beach Toys, Fence Around The Yard, Bicycle (2 Adult Bikes, 1 Children Bikes), Private Pool (Outdoor, Heated, Freshwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning (Central Air), Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Private Entrance, Parking, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Heating, Usable Fireplace (Wood-Burning), Ice Maker, Coffee (Nespresso, Keurig), Laptop-Friendly Workspace, Pots and Pans, Television (Den), Smart TV, Wine Fridge, Speaker System (Sonos), Pack 'n Play/Travel Crib, Privacy (Completely Private), Gym/Fitness Room (Weight Training Equipment) Special Features 15 minute drive to each of Sag Harbor, Southampton and Bridgehampton. Walking distance (0.7 miles / 14min walk ) to beach Location Nearby Beaches: Cooper’s Beach Flying Point Beach Halsey Neck Beach Cryder Beach Little Plains Beach Nearby Grocery Stores: Hank’s Farmstand Southampton Farmer’s Market Citarella Stop & Shop Nearby Restaurants and Bars: AM Southampton Southampton Social Club Claude’s Restaurant The Plaza Caf Southampton Social Club Union Cantina Union Burger Bar Sant Ambroeus 75 Main Tutto il Giorno Le Chef Other Location Information: Agawam Lake Park Shinnecock Hills Golf Club Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 2,200 Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: Pets may be allowed but are subject to owner’s approval (please inquire). Pet approval may include additional fees and/or security deposit. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $95.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $100.00 per person per night may be required. Events Policy: Events are prohibited unless express approval is provided. An event fee of $5,000.00 may be required. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

North Sea Bungalow

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 23 - 30
$845 night

North Sea Bungalow Newly-Renovated Southampton Cottage, Open Floor Plan, Great Room with Mid-Century Style Fireplace, Close to Marina and Ocean Beaches 3BR/2BA with island kitchen, breakfast area, Nespresso coffee machine, fireplace, Sonos/Bluetooth speaker system, primary suite with patio access, children’s bicycles, charcoal grill, fitness room Experience modern beach living in Southampton year-round in this newly-renovated cottage. Located on a private road, the home sits on a grassy quarter acre, fenced-in to ensure safety for the whole family. The professionally-designed interior features an open floor plan with high vaulted ceilings and clean, crisp white walls. Tall, large windows surround the main living area, bringing in a ton of natural light. Gather and relax in the airy, bright great room with a cozy mid-century style wood fireplace and a Smart TV. Play lively background music using the Sonos and Bluetooth speaker system. Whip up a delicious breakfast in the spacious, updated island kitchen with quartz countertops, stainless steel appliances, and a wine fridge. Sip coffee brewed with the Nespresso machine at the breakfast area with seating for three. Break bread in the open dining room with a table that seats six and overlooks the backyard. Access the landscaped rear yard through glass doors by the dining area. Perfect for summer entertaining and dining al fresco, the yard features a patio and a charcoal grill. Do a self-guided yoga class and use the weight training equipment in the fitness room. Watch the little ones ride the two children’s bicycles on the quiet road. Take the supplied kayak and paddle board to the marina, a short walk away. Strong’s Southampton Peconic Bay Marina allows you to rent a boat for water skiing, tubing, fishing, or cruising around in the fresh Hamptons air. Grab the four beach chairs, umbrella, toys, and cooler for a day of fun in the sun at Crab Beach, a two-minute drive away. Retire to the three lovely bedrooms, including the primary suite and two guest rooms that share a bath. In its own wing, the gorgeous primary bedroom suite contains sliding glass windows opening out onto the patio, a walk-in closet, and a master bath complete with spa-like pebble floors, a soaking tub, and a separate shower. For your convenience, a washer and dryer are in the front of the house by the guest rooms. North Sea Bungalow is sure to be the getaway of your dreams. This property has a max occupancy of 6 Bedrooms Bedroom 1: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, Closet Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning Bedroom 3: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Closet, Balcony/Deck Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Outdoors Deck/Patio (Uncovered), Lounge Chairs (2 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Charcoal), Bicycle (2 Children Bikes), Beach Chairs (4 Chairs), Beach Umbrella, Beach Toys, Cooler, Kayak/Canoe, Paddle Board, Fence Around The Yard Amenities Bed Linens, Bath Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Private Entrance, Parking, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Hair Dryer, Iron/Ironing Board, Usable Fireplace (Wood), Wine Fridge, Coffee (Pot, Nespresso), Toaster, Blender, Smart TV, Speaker System (Bluetooth Speaker, Sonos), Gym/Fitness Room (Weight Training Equipment, Stretching / Yoga Mat) Suitability: Not suitable for unrelated guests and persons with disabilities. Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Normal usage of the following utilities is included in the total reservation amount: Heating Oil/Propane/Natural Gas, Electricity, Cable/TV/Internet/Phone, Garbage Removal, and Landscaping/Lawn Maintenance If the cost of utilities exceeds $50.00/night, guest will be responsible for the difference. Cleanings during a guest’s stay and pay-per-view orders are not included in the cost of utilities. Cleaning Disclaimer: All reservations longer than one week must be professionally cleaned once per week, the cost of which is borne by the guest. For clarity purposes, the cost of in-stay cleanings are separate and above the fees collected at the time of booking. Additional Persons: No additional persons beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. StayProtected Insurance: Property damage insurance is procured for your reservation for this property. It is supplemental to, not a replacement to, any security deposit collected. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property.

Seasons Lane Sensation

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 11 - 18
$1,046 night

Seasons Lane Sensation Stately traditional home with open floorplan and private pool in coveted Southampton Village. 5BR/5.5BAElegantly furnished traditional home with oversized rooms, multiple fireplaces, updated kitchen, private heated pool, and community tennis courts! Located in a prime Southampton Village neighborhood, this refined traditional home has five bedrooms, five-and-a-half bathrooms and over 4,000 square feet of living space set on .46 acres of beautifully landscaped grounds. Through the double-height foyer, gleaming dark hardwood flooring carries throughout the main level of the home and the fresh white walls amplify the natural light that filters through the many windows. In the formal sitting room, a fireplace with marble tile and beautiful millwork mantle is surrounded by a sofa and several armchairs and chaise lounges. The room overlooks the pool with easy access to the patio through the sliding door. The formal dining room is equally elegant with a long wood table and upholstered seating for eight and a sideboard for easy service. A casual media room and office space are also found on the main level. The kitchen is spacious with a prep island as well as a peninsula counter for informal seating. The rich wood cabinetry is nicely complimented by the dark granite countertops and the stainless-steel appliance suite that includes a five-burner gas range. Directly adjacent is the informal dining space with seating for four. Each of the five bedrooms are spacious with their own ensuite baths. In the master suite, find a fireplace and private balcony that overlooks the backyard. The ensuite bath includes double sinks, vanity, tiled shower, and a jetted soaking tub. The large brick paver patio in the backyard surrounds the heated pool and includes a gas grill with a full patio set including a dining table and chairs, and several loungers. A community tennis court and playground are also available for use. Located just minutes to local beaches and Southampton village, this home is ideally located for your next getaway! This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet, Balcony/Deck Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Standard Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Standard Closet Bedroom 5: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Standard Closet Bathrooms Bathroom 1: Half Bath, First Floor/Main Floor Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 6: Full Bath, 2nd Floor, Ensuite, Shower TVs Bedroom 1 Bedroom 2 Bedroom 3 Bedroom 4 Bedroom 5 Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (7 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Communal), Fence Around The Yard, Private Pool (Outdoor, Heated, Freshwater) Amenities Washer, Dryer, Air Conditioning, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Cable TV, Smart TV, Speaker System (Sonos), Parking (4 Cars In Driveway), Garage (2 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Bed Linens, Hair Dryer, Usable Fireplace, Bath Towels, Pool/Beach Towels, Laptop-Friendly Workspace, Pots and Pans, Essentials, Blender Location Nearby Beaches: Coopers Beach Nearby Grocery Stores: Stop and shop Citarella Shmidts Nearby Restaurants and Bars: Le Charlotte Sant ambroeus Golden pair Pauls pizza Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 4,000 Suitability: Not handicap accessible. Not suitable for multiple families and unrelated guests. Primary renter must be at least 30 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $150.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. An additional guests fee of $1,000.00 per person per night may be required. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Summerset Villa | Home w/ Pool

Bridgehampton, NY, US
4 Bedrooms 8 Guests
Sep 11 - 18
$3,500 night

Welcome to Summerset Villa, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Welcome to Summerset Villa, a reimagined barn estate in the heart of Bridgehampton. Just moments from town and the beach, this four-bedroom, three-and-a-half-bath retreat offers a peaceful escape with easy access to local shops, dining, and transportation. Originally the Ludlow Grange Barn, this 6,000 square-foot home was rebuilt in 2014 with soaring ceilings, open interiors, and thoughtful design. The main level features a dramatic great room, a sleek chef’s kitchen with views of the pool, and three spacious bedrooms connected by a striking hallway. Upstairs, a private guest suite accessed via exterior stairs includes a fourth bedroom, gym, office, and additional living area. The U-shaped layout wraps around a landscaped English garden and a heated gunite pool with hot tub, offering privacy and serenity. Set back 500 feet from the road, the property feels tucked away while remaining close to everything. Bikes, surfboards, and beach gear are also provided. Whether you’re exploring the Hamptons or relaxing at home, Summerset Villa is designed for comfort, convenience, and style. Pet Policy: Pets are allowed at this property for an additional $350 fee. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. Please note that mid-stay cleans can be arranged upon request with our partner for an additional fee. Cleaning costs is contracted with the cleaners and paid to them directly. If you want the pool heated during your stay, there is an additional $75/night fee. Note, utilities including pool heating are billed separately for all stays over 14 nights. The pool is open seasonally. As a reminder, smoking is not allowed anywhere on the property, in the home or in the outside areas of the home. Smoking will result in a odor removal fee of no less than $500 and up to $1,000 as well as possible removal from the property. Security deposit A refundable credit card hold of $1,000 is required as a security deposit for stays at this home to cover any property damage that may occur during your stay. A credit card is required for processing and the hold will be placed 48 hours prior to your arrival. The release of this hold will initiate 2 days after your departure following a departure inspection of the home by our local team.

The Summermill House

Water Mill, NY, US
3 Bedrooms 8 Guests
Sep 11 - 18
$1,569 night

The Summermill House Stunning shingled Water Mill estate featuring a private heated pool and fenced yard, the perfect getaway for families or groups of friends 3BR/3.5BA: Additional Sleep Space, Heated Pool, Bicycles, Weight Training Equipment, Gas Grill, Ping Pong, and Sonos Tucked away on a quiet private block in the heart of Water Mill, this stunning shingled estate offers the perfect balance of luxury, comfort, and effortless Hamptons living. Designed with families and groups of friends in mind, the home welcomes guests into a warm and inviting atmosphere where open living spaces and thoughtful design create an immediate sense of relaxation. With 3 bedrooms, 3.5 bathrooms, and additional sleeping space, the property comfortably accommodates guests seeking a peaceful retreat just moments from Southamptons world-renowned beaches, dining, and shopping. Whether gathering for a summer escape, celebrating a special occasion, or simply stepping away from the pace of everyday life, this beautifully appointed residence creates an unforgettable backdrop for every stay. The outdoor setting is equally exceptional, designed to maximize privacy and enjoyment throughout every season. Surrounded by mature landscaping and fully fenced for seclusion, the backyard feels like a private resort tucked away in the Hamptons. Guests can spend long afternoons lounging beside the heated pool, enjoying morning coffee beneath the open sky, or hosting evening dinners fresh off the gas grill. The property also includes bicycles for leisurely rides through the surrounding neighborhood, ping pong for friendly competition, and private weight training equipment for those who enjoy maintaining wellness routines while traveling. Every outdoor detail has been thoughtfully curated to create an environment that feels serene, spacious, and entirely removed from the outside world. Inside, the homes open-concept layout is flooded with natural light, creating an airy and welcoming ambiance throughout the main living spaces. The seamless flow between the living room, dining area, and gourmet kitchen allows guests to gather comfortably while still enjoying plenty of room to unwind. The living room offers a sophisticated yet cozy setting to relax after a day at the beach, complete with comfortable seating and a premium Sonos sound system that enhances the atmosphere throughout the home. The chefs kitchen is outfitted with top-of-the-line appliances, generous counter space, and everything needed for preparing everything from casual breakfasts to elegant dinners at home. A coffee maker is ready for slow Hamptons mornings, while the dining area provides the perfect setting for shared meals and conversation. Modern conveniences including high-speed Wi-Fi, central air conditioning, and an in-home washer and dryer ensure every stay feels as effortless as it is luxurious. The homes sleeping accommodations have been carefully designed to provide both comfort and privacy for every guest. Each bedroom offers a peaceful retreat with plush bedding, fresh linens, and thoughtfully appointed furnishings that create a restful atmosphere. The additional sleeping space allows flexibility for families or groups traveling together, while the 3.5 bathrooms ensure convenience and comfort throughout the stay. Spa-inspired bathrooms feature clean, elegant finishes and are stocked with the essentials guests need to settle in immediately upon arrival. From quiet mornings to restful evenings, every detail throughout the home has been curated to make guests feel completely at ease. Beyond the property, guests are ideally positioned to experience the very best of the Hamptons lifestyle. Located just a short drive from Southamptons pristine ocean beaches, acclaimed restaurants, charming boutiques, art galleries, wineries, and premier golf courses, the home places guests close to everything while still offering total privacy when it is time to return home and unwind. Days can be spent exploring nearby coastal towns, enjoying waterfront dining, shopping local markets, or relaxing on some of the East Coasts most beautiful beaches. Whether guests are seeking a laid-back coastal escape or a refined Hamptons getaway filled with memorable experiences, this exceptional Water Mill estate delivers luxury, comfort, and timeless charm in one of the areas most sought-after locations. This property has a max occupancy of 8 Bedrooms Bedroom 1 - Primary: One Queen Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Closet, Balcony/Deck Bedroom 2: One Double/Full Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Basement: Two Sleep Sofas, Lower Level, Air Conditioning, Streaming TV, Standard Closet, Open Area Privacy Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, 2nd Floor, Ensuite, Shower, Shower/Tub Combo Bathroom 2: Half Bath, First Floor/Main Floor Bathroom 3: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 4 - Basement: Full Bath, Lower Level, Shower TVs Basement: Streaming Outdoors & Pool/Spas Balcony, Bicycle, Deck/Patio (Covered), Grill (Gas), Beach Chairs, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Pool, Fence Around The Yard, Fire Pit (Wood-Burning, Gas), Private Pool (Heated, Outdoor) Amenities Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Dishes and Silverware, Pots and Pans, Toaster, Blender, Television (Main Living Room), Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Laptop-Friendly Workspace, Usable Fireplace (Wood-Burning), Gym/Fitness Room (Weight Training Equipment), Iron/Ironing Board, Coffee (Pot), Ping Pong Table, Speaker System (Sonos), Fire Extinguisher, Wine Fridge, Ice Maker, Privacy (Completely Private), Private Entrance, Essentials Location Nearby Beaches: Flying Point Beach W. Scott Cameron Beach Ocean Road Beach Nearby Grocery Stores: The Green Thumb Halsey Farm & Nursery Nearby Restaurants and Bars: Duck Walk Hamptons Provisions Natural Foods Market Calissa Bistro Ete Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: No Suitability: Primary renter must be at least 30 years old. Pet Policy: One dog of 20 lbs or less is permitted for an additional $200.00 per booking. Dogs over 20 lbs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $75.00 per night of the reservation. Cleaning Disclaimer: One end of stay cleaning is included in the reservation total. For reservations longer than seven nights, one cleaning per week is mandatory. In-stay cleanings are the guest’s expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. While Property Manager manages this listing, the guest experience is managed by the owner of this property, meaning all property preparation, arrival coordination, in-stay communication, and requests for maintenance tasks are performed by the owner. However, Property Manager will provide you with a "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. Guest Experience: This property is part of our ’Elite’ program, where the homeowner manages all on-the-ground operations and guest communication after the booking is confirmed. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Huckleberry Hideaway

Sag Harbor, NY, US
7 Bedrooms 14 Guests
Sep 13 - 16
$815 night

Huckleberry Hideaway Expansive Sag Harbor Estate with Pool, Tennis, Hot Tub, Close to Sag Harbor and Bridgehampton 7BR/8BA: private heated pool, hot tub, Har-Tru clay tennis court, finished lower level, office, Peloton bike, pool house, expansive outdoor dining area Welcome to this magnificent Sag Harbor estate, where luxurious living meets ultimate comfort. This stunning property features seven spacious bedrooms and eight pristine bathrooms, comfortably accommodating up to 14 guests. With its bright, airy interiors and multiple sitting and dining areas, this home is an idyllic retreat for families or large groups looking to escape daily life. Nestled on a serene private block, this estate promises peace and tranquility. The exterior of this property is nothing short of spectacular. Guests can enjoy total privacy while relaxing on the expansive deck, which boasts an outdoor dining area and a gas BBQ. The deck leads to a heated pool, perfect for refreshing swims, as well as a hot tub, fire table, and private tennis court for endless entertainment. For pickle ball enthusiasts, a portable net is at your disposal for a quick game. A charming pool house and multiple sitting areas provide ideal spots for evening cocktails. The vast yard offers plenty of space for outdoor activities, and ample free parking ensures convenience for all guests. Step inside and be captivated by the home’s open layout and abundance of natural light. The estate is equipped with modern conveniences such as WiFi, a washer and dryer, and central AC, ensuring a comfortable stay. The open living spaces flow seamlessly from the living room, with its cozy fireplace, to the elegant dining room and gourmet kitchen. The kitchen is a chef’s dream, featuring top-of-the-line appliances and a coffee maker. For those needing to work from home, there is a dedicated workspace, and the finished lower level includes an additional media area, office and Peloton bike. Each bedroom is a haven of comfort, outfitted with fresh linens and all the essentials you need for a restful night’s sleep. The bathrooms are elegantly designed, offering a spa-like experience with high-quality fixtures and finishes. Conveniently located close to Sag Harbor, Southampton, and Water Mill, this estate is perfect for exploring the best of the Hamptons. Golf enthusiasts will appreciate the proximity to Noyac Golf Club and The Bridge Golf Club, while nature lovers can explore the nearby Noyac County Park and Sag Harbor Beaches. Whether you seek relaxation or adventure, this expansive Sag Harbor estate is the perfect base for your Hamptons getaway. This property has a max occupancy of 14 Bedrooms Primary Bedroom: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet, Balcony/Deck Bedroom 4: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 5: One Double/Full Bed, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 6: One King Bed, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 7: One Queen Bed, Lower Level, Air Conditioning, Full Ensuite Bathroom, Standard Closet Bathrooms Primary Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Primary Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 4: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 5: Full Bath, First Floor/Main Floor, Ensuite, Shower/Tub Combo Bathroom 6: Full Bath, Lower Level, Ensuite, Jack & Jill, Shower Bathroom 7: Full Bath, Lower Level, Ensuite, Shower Pool House Bathroom 8: Full Bath, Pool House First Floor/Main Floor, Shower TVs Primary Bedroom: Streaming Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 4: Streaming Bedroom 5: Streaming Bedroom 6: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Private), Fire Pit (Gas), Outdoor Shower (Hot + Cold Water), Tennis Equipment (Rackets, Balls), Beach Chairs, Beach Umbrella, Cooler, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated), Hot Tub (Freestanding Hot Tub) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Blender, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Main Living Room, Media Room), Private Entrance, Parking, Smoke Detector, Essentials, Dishes and Silverware, Hair Dryer, Usable Fireplace (Wood-Burning), Smart TV, Garage, Carbon Monoxide Detector, Fire Extinguisher, Gym/Fitness Room (Stationary Bike) Special Features Please note the hot tub and tennis court are both available MDW through mid-October. If your booking falls outside of that time frame and you intend to use the hot tub or tennis court, please be sure to inquire if it will be available prior to booking. Location Nearby Beaches: Foster Memorial Town Beach (5 min drive) Circle Beach (5 min drive) Sagg Main Beach (15 min drive) Ocean Road Beach (15 min drive) Nearby Grocery Stores: Cromer’s Market (5 min drive) Sag Harbor Farmer’s Market (10 min drive) Schiavoni’s Market (10 min drive) Provisions Natural Foods Market (15 min drive) Nearby Restaurants and Bars: Bell & Anchor (3 min drive) MJ Dowling’s (5 min drive) Eds Lobster Bar (10 min drive) Estia’s Little Kitchen (10 min drive) The Dock House (10 min drive) DOPO La Spiaggia (10 min drive) Murf’s Backstreet Tavern (15 min drive) Murf’s Backstreet Tavern (15 min drive) The Beacon (15 min drive) Le Bilboquet (15 min drive) Sag Harbor Tavern (15 min drive) Other Location Information: Elizabeth A Morton National Wildlife Refuge (3 min drive) Sag Habor State Golf Course (20 min drive) Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 5,306 Suitability: Not handicap accessible. Primary renter must be at least 28 years old. Pet Policy: One hypoallergenic/non-shedding dog permitted for an additional $200.00 per booking. Non hypoallergenic/shedding dogs are prohibited unless express approval is provided. All other pets (including multiple dogs) are prohibited unless express approval is provided (please inquire). Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $200.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Hot Tub is only available for use from Memorial Day through approximately mid-October. If your booking falls outside of that time frame and you intend to use the hot tub, please be sure to inquire if it will be available prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not the tennis court, outdoor furniture, and equipment will be available for use prior to booking. Note that the pool house is not available/usable from Oct-May as it is winterized for the season. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Southampton Pool Home Near Village

Hamptons, NY, US
4 Bedrooms 8 Guests
Sep 11 - 14
$924 night

A bright, comfortable Southampton home with a large private yard, heated pool (seasonal), hot tub, fire pit, and two spacious living rooms—ideal for families and small groups. Located on a quiet street just minutes from Southampton Village and 3.6 miles from Shinnecock Hills. Sleeps 8 across 4 bedrooms, all on one level. Fast WiFi, outdoor dining, and plenty of space to unwind. Welcome to Your Southampton Retreat Set on nearly a half acre with a large backyard, heated pool (seasonal), hot tub, and multiple outdoor seating zones, this classic Southampton home is designed for relaxed days outside and comfortable nights in. Two living rooms, four bedrooms, and a clean, open layout make it perfect for families, golf groups, and friends who want an easy, quiet base close to everything. The Home (Sleeps 8) All bedrooms and living areas are on one level—excellent for multi-gen families, long stays, and easy flow. Living Spaces • Two large living rooms — both with oversized sofas and smart TVs • Skylights + natural light • Fireplace (for cool evenings) • Hardwood floors • Central A/C • Fast WiFi (work-friendly) • Dining area for 6 • Bonus lounge seating in the den This “dual-living-room” setup is a major advantage over comparable 4BR homes, especially for groups wanting separate spaces. Kitchen • Stainless steel appliances • Eat-in table (seats 6) • Kitchen island with stool seating • Pass-through window to the den • Full cookware, serveware, and essentials Bedrooms (All First Floor) Bedroom 1 — King bed + ensuite bath Bedroom 2 — King bed Bedroom 3 — Queen bed Bedroom 4 — Queen bed Additional — Queen sleeper sofa in den Sleeps 8 comfortably (10 if using the sleeper). Bathrooms (2 Total) • Ensuite bathroom with shower/tub combo • Additional full bath with shower/tub combo Both are clean, simple, and well-kept. Outdoor Space Your private backyard is the centerpiece of the home: • Heated pool (Memorial Day–Labor Day; $45/day heat) • Hot tub (available year-round; $95 cleaning fee) • Bluestone patio with outdoor dining • Loungers + umbrellas • Large lawn ideal for play and relaxation • Fire pit • Gas grill • Outdoor shower • Private driveway (space for 4 cars) This yard is larger than typical Southampton lots in this price tier, and the privacy buffer is a competitive advantage. Minutes from historic Shinnecock Hills Golf Club. An ideal location for golf enthusiasts visiting one of the country’s most iconic courses. • 3.6 miles to Shinnecock Hills Golf Club • Easy local access without major road bottlenecks • Two living rooms (great for groups) • 2 King bedrooms — ideal for staff or executives • Fast WiFi • Quiet, private yard for downtime • Parking for 4 cars Perfect for: • Player support teams • Media crews • Corporate groups • Serious fans needing a comfortable retreat Event-week pricing available on request. Good Fit For • Families • Golf + tournament groups • Multi-generational stays • Couples traveling together • Guests wanting privacy + pool + hot tub Not Ideal For • Large parties • Guests requiring a walkable beach • Noise-sensitive neighbors (quiet hours strictly enforced) Seasonal Notes Outdoor furniture, grills, pool equipment, and yard amenities are typically available Memorial Day through Labor Day. They are stored between Columbus Day and Memorial Day. Hot tub is available year-round. • For stays of 21 days or more, utility expenses, including electricity and gas/oil charges, will be calculated based on the actual duration of the guest’s stay upon receipt of the utility bills from the Owner. • Stays 29+ nights: refundable security deposit required Important Details • Primary renter must be 25+ • Pets: case-by-case with fee • Pool heat: $45/day • Hot tub cleaning: $95 per service • Cleaning fee: $450 • Exterior driveway camera present (for security only) Guests have full private access to the entire home, yard, pool, and hot tub. The home is in a quiet residential pocket of Southampton with quick access to major roads and the village. Cancellation Policy - Bookings canceled at least 30 days before the start of stay will receive 100%. - Bookings canceled at least 14 days before the start of stay will receive a 50% refund. Guest Insurance Please note, as a part of booking we secure insurance for your stay and will require you to sign a Guest Rental Agreement. This insurance is meant to cover any incidental damages to the property that may occur during your stay and does not cover any issues with your trip related to cancellation due to illness or other reasons. We understand that things happen by mistake or accident from time to time, we ask that you let us know when it happens. You’re covered with us - we’re invested in you having a worry-free stay! Our Company Luxury Beach Getaway has been proudly offering a curated selection of vacation home rentals in the Hamptons and North Shore since 2008, and we look forward to hosting your wonderful stay. Thank You, Debbie & Scott

Vacation Rentals in Water Mill by Amenities & Features

Get to Know Water Mill

Water Mill, New York, is a picturesque hamlet located in the town of Southampton on Long Island's prestigious South Fork. Known for its rural charm, historic landmarks, and proximity to some of the most beautiful beaches on the East Coast, Water Mill offers a serene escape from the hustle and bustle of city life. One of the hamlet's most iconic landmarks is the Water Mill, for which the area is named. This historic gristmill is a testament to the area's rich history and is part of the Water Mill Museum, where visitors can learn about the hamlet's past and its significance during the colonial era. Art enthusiasts will find a haven at the Parrish Art Museum, which showcases an impressive collection of American art with a focus on works from the Long Island region. The museum's striking architecture and beautifully landscaped grounds make it a cultural centerpiece in the community. For those who appreciate the great outdoors, Water Mill's natural beauty is on full display at the local vineyards and farms, where visitors can enjoy wine tasting and pick up fresh, local produce. The hamlet's proximity to the Atlantic Ocean means that beachgoers can bask in the sun at nearby Cooper's Beach, often ranked among the top beaches in the United States for its pristine white sand and clear blue waters. Water Mill is also a prime spot for those interested in architecture and real estate, as it boasts some of the most luxurious homes in the Hamptons. A drive through the tree-lined streets reveals stunning estates and manicured gardens that reflect the affluence and exclusivity of the area. The hamlet's dining scene offers a range of options from casual eateries to upscale restaurants, many of which feature locally sourced ingredients and seafood fresh from the nearby waters. The relaxed yet sophisticated atmosphere of Water Mill's dining establishments perfectly complements the overall vibe of the area. In essence, Water Mill is a destination that offers tranquility, culture, and natural beauty. It's a place where visitors can immerse themselves in the laid-back luxury of the Hamptons, enjoy the arts, savor fine dining, and unwind in a setting that is both historically rich and scenically splendid. Whether you're looking for a peaceful retreat or an upscale getaway, Water Mill is a place that truly caters to those in search of an exclusive and memorable experience.
Water Mill, New York, nestled within the scenic Hamptons on Long Island, experiences a climate that is both seasonal and inviting, with variations that cater to a range of preferences throughout the year. The summer months, from June to August, are the most popular and lively, with warm temperatures averaging in the high 70s to mid-80s Fahrenheit. The Atlantic Ocean provides a cooling breeze that makes the humidity more tolerable, and occasional thunderstorms can offer a refreshing break from the heat. This is the peak season for beachgoers, sunbathers, and those looking to enjoy the quintessential Hamptons experience. Autumn, from September to November, is a particularly pleasant time in Water Mill. The temperatures cool to a comfortable range of the 60s to low 70s, and the humidity drops, making it ideal for outdoor activities like apple picking, wine tasting at local vineyards, and enjoying the fall foliage. The crowds also thin out after Labor Day, providing a more relaxed atmosphere. Winter, from December to February, is the quietest season, with temperatures ranging from the 30s to the 40s. Snowfall can transform the landscape into a picturesque winter wonderland, but it's also the time when many seasonal businesses are closed. Those looking for a serene getaway might find this time of year appealing, though it's essential to be prepared for the colder weather. Spring, from March to May, sees a gradual warming with temperatures climbing from the 40s to the 60s. The blooming flowers and greening landscapes make it a beautiful time to visit, though it can be a bit unpredictable with occasional rain showers and a lingering chill in the air. The most pleasant climate is often found in the late spring to early summer and then again in the early fall, when the weather is warm but not too hot, and the humidity is lower. These shoulder seasons offer the best of both worlds: comfortable weather and fewer crowds, allowing visitors to enjoy the natural beauty and charm of Water Mill without the peak season rush. Whether you're looking to relax on the beach, explore the local art scene, or simply enjoy the tranquil surroundings, Water Mill has a season for every traveler's preference.
Water Mill, New York, may be a small hamlet in the Hamptons, but it offers a rich cultural experience for those who seek the arts, history, and local customs. This picturesque destination is a haven for art enthusiasts, history buffs, and those looking to immerse themselves in the local culture of the East End of Long Island. Begin your cultural journey at the Water Mill Center, an interdisciplinary laboratory for the arts and humanities founded by theater and visual artist Robert Wilson. This unique space offers a wide range of programs, including exhibitions, performances, artist residencies, and educational initiatives. The center's lush grounds and innovative installations provide a serene backdrop for contemplation and inspiration. For a deep dive into the history of the area, visit the Water Mill Museum. Housed in a restored 1644 watermill, the museum showcases the history of the mill and the surrounding community. The museum's exhibits include artifacts from the mill's operational days, providing a glimpse into the industrial past of the Hamptons. Art galleries in Water Mill, such as the Sara Nightingale Gallery, offer a look at contemporary art with rotating exhibitions featuring local and international artists. These intimate spaces provide an opportunity to engage with the art community and perhaps find a unique piece to take home. Live music can be enjoyed during the summer months at the Parrish Art Museum's outdoor concerts, where the sounds of classical, jazz, and contemporary music fill the air amidst the museum's stunning architecture and sculpture garden. The Parrish Art Museum itself is a destination for art lovers, with a collection that focuses on works that represent the rich artistic legacy of Long Island's East End. Local customs and the agricultural heritage of Water Mill can be experienced at the local farm stands and vineyards. The Hamptons' farm-to-table movement is alive and well here, with fresh, locally sourced produce and wines that reflect the terroir of the region. Seasonal events, such as harvest festivals, offer a chance to celebrate with the community and enjoy the bounty of the land. Water Mill's tranquil setting, combined with its cultural offerings, makes it an ideal destination for those looking to indulge in the arts, explore history, and experience the local customs of the Hamptons. Whether strolling through art galleries, attending a live performance, or savoring the local cuisine, Water Mill provides a cultural retreat that is both enriching and relaxing.
Water Mill, New York, nestled in the picturesque Hamptons, offers a serene escape with a variety of activities that children will love. This charming community, with its blend of rural beauty and cultural sophistication, provides a delightful backdrop for family adventures. Begin your visit at the Children's Museum of the East End (CMEE). This interactive museum is designed specifically for kids, with exhibits that encourage play, learning, and creativity. Children can explore a variety of hands-on displays, including a pretend grocery store, a fishing boat, and a musical forest. The museum also offers workshops and special events that are both fun and educational. For outdoor enthusiasts, the Elizabeth A. Morton National Wildlife Refuge is a must-see. Kids will be thrilled to encounter wildlife up close as they walk the trails. The refuge is home to a variety of birds, turtles, and other animals. Don't forget to bring some birdseed; the friendly chipmunks and birds will eat right from your hand, providing an unforgettable experience for the little ones. If your family enjoys art, the Parrish Art Museum is a cultural gem that features works by many artists from the region. While the museum's collection may appeal more to adults, the museum often hosts family-friendly events and offers art classes and workshops for children, making it a great place to foster a young one's appreciation for art. For a day at the beach, Flying Point Beach is one of the area's most beautiful spots. The gentle waves and soft sand make it an ideal location for building sandcastles, paddling in the shallows, or simply enjoying a picnic with the family. During the summer months, the Water Mill Community Club hosts various family-oriented events, including barbecues and outdoor movie nights, which are perfect for enjoying those warm Hampton evenings. Lastly, no visit to Water Mill would be complete without a stop at the iconic Water Mill. This historic grist mill, which dates back to the 17th century, is not only a great photo opportunity but also a chance to teach children about the area's history and the workings of a water-powered mill. Water Mill offers a tranquil yet engaging environment for families, where children can enjoy both educational and recreational activities amidst the natural beauty and cultural richness of the Hamptons.
Water Mill, New York, nestled within the scenic Hamptons on Long Island, offers a serene escape into nature's embrace, with a variety of outdoor activities and natural wonders that cater to the nature enthusiast. One of the area's most picturesque spots is the Elizabeth A. Morton National Wildlife Refuge. Spanning 187 acres, this sanctuary is a haven for wildlife and a paradise for birdwatchers. The refuge's diverse habitats, including salt marshes, freshwater ponds, and beaches, are home to a variety of bird species, as well as other wildlife. Visitors can enjoy tranquil walks along the trails, where they may encounter animals such as wild turkeys, chipmunks, and even white-tailed deer. For those who love the water, Mecox Bay offers a splendid opportunity for kayaking and paddleboarding. The calm waters are ideal for beginners, while the scenic surroundings provide a peaceful backdrop for a day on the water. Fishing enthusiasts can also find spots along the bay to cast a line and relax in the quiet beauty of the area. The nearby ocean beaches, such as Flying Point Beach, provide a classic Hamptons experience with pristine sands and rolling waves. Here, one can indulge in sunbathing, beachcombing, or take a refreshing swim in the Atlantic Ocean. The beaches also offer spectacular sunrise and sunset views, perfect for photographers and romantics alike. For a more secluded outdoor experience, the trails and paths that wind through the area's farmland and vineyards offer a chance to explore the rural charm of Water Mill. Hiking or cycling through these landscapes allows visitors to appreciate the region's agricultural heritage and perhaps stop for a wine tasting at a local vineyard. Lastly, the Parrish Art Museum, while not a natural wonder, is surrounded by meadows that provide a serene setting for a leisurely walk. The museum's outdoor sculptures blend art with the natural environment, creating a unique cultural experience in the midst of nature. Water Mill's combination of wildlife refuges, water activities, beautiful beaches, and pastoral landscapes make it an idyllic destination for outdoor lovers looking to connect with nature in a tranquil and exclusive setting.
Water Mill, New York, is a picturesque hamlet in the Town of Southampton on Long Island and is part of the storied Hamptons region. This tranquil destination is not served by its own airport, so travelers typically fly into one of the New York City airports – JFK International Airport or LaGuardia Airport – and then make their way to Water Mill. The nearest major airport is Long Island MacArthur Airport, located about 40 miles away, which offers a more limited range of flights. Upon arrival at one of the airports, visitors can rent a car, which is the most convenient way to reach Water Mill and explore the surrounding Hamptons area. Alternatively, the Hampton Jitney provides a comfortable and direct bus service from New York City to various points in the Hamptons, including Water Mill. For those who prefer train travel, the Long Island Rail Road (LIRR) operates services to the Hamptons from Penn Station in Manhattan, with the nearest stop to Water Mill being in Southampton. Once in Water Mill, having a car is advantageous for getting around, as the hamlet and the wider Hamptons area are spread out, and public transportation options are limited. The area is known for its beautiful beaches, art galleries, and wineries, which are best accessed by car. Ride-sharing services like Uber and Lyft are also available and can be a convenient option for those who do not wish to drive. Cycling can be a pleasant way to enjoy the scenic beauty of Water Mill, especially during the warmer months. However, the area does not have extensive bike lanes, so it's important to be cautious when sharing the road with vehicles. Water Mill itself is not particularly walkable due to the distances between attractions and the lack of sidewalks in many areas. However, for those staying within the hamlet, there are a few local shops, restaurants, and the renowned Parrish Art Museum that can be reached on foot. In summary, while Water Mill exudes a serene and rural charm, it is best explored with access to a car. The area's sprawling estates, vineyards, and beaches are not easily accessible by public transport, making driving the most flexible and convenient way to experience the beauty of this quintessential Hamptons destination.

Water Mill FAQs

Water Mill offers a variety of activities for visitors. You can explore the Parrish Art Museum, which features American art with a focus on works from the Long Island area. The Water Mill Community Club hosts events and gatherings. For outdoor enthusiasts, the area is great for biking, and there are beautiful beaches nearby, such as Flying Point Beach. Wine lovers can enjoy local vineyards like Duck Walk Vineyards. Don't miss the Water Mill Museum for a bit of local history, and if you're visiting in the summer, the annual Water Mill Summer Benefit is a highlight.
The best time to visit Water Mill is during the summer months from June to August when the weather is warm and all the local attractions and beaches are fully accessible. However, if you prefer a quieter visit, the shoulder seasons of spring and fall offer mild weather and fewer crowds.
Yes, Water Mill has a range of accommodations, from charming bed and breakfasts to private vacation rentals. While there aren't many large hotels in the immediate area, nearby Southampton offers additional lodging options.
Water Mill has a selection of dining options that range from casual cafes and delis to upscale restaurants. Local seafood is a specialty, and many establishments offer dishes featuring fresh, locally sourced ingredients.
Water Mill is accessible by car, and it's a popular road trip destination for those coming from New York City or other parts of Long Island. The nearest airport is in Southampton, but the larger airports in New York City are also commonly used by travelers. Additionally, the Long Island Rail Road (LIRR) and the Hampton Jitney bus service provide transportation from New York City to the Hamptons area.
Absolutely! Families can enjoy the beaches, go for bike rides, or visit the Children's Museum of the East End in nearby Bridgehampton. The area also has farms where you can pick your own fruit or enjoy a hayride, and the South Fork Natural History Museum and Nature Center is a short drive away.

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