Vacation rentals in The Hamptons, NY with a pool

Explore 103 vacation rentals, homes, and villas with pools in The Hamptons, NY for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Air Condition Homes, Best Affordable Homes and Great for Groups. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $115 per night and homes offering up to 8 bedrooms and 11 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

103 Homes with Pools in The Hamptons

Water Mill Towd Terrific

Water Mill, NY, US
6 Bedrooms 16 Guests
Sep 14 - 21
$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.

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 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.

Water Mill Wooded Escape

Water Mill, NY, US
4 Bedrooms 8 Guests
Sep 14 - 16
$1,227 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.

Southampton Paradise

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 14 - 21
$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.

Old Trail Tranquility

Water Mill, NY, US
5 Bedrooms 12 Guests
Sep 14 - 17
$793 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.

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.

Stately, Upscale Home with Stunning Pool Deck & Amazing View

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 20 - 23
$732 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 14 - 17
$1,281 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.

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.

The Summermill House

Water Mill, NY, US
3 Bedrooms 8 Guests
Sep 14 - 21
$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.

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.

Southampton Pool Home Near Village

Hamptons, NY, US
4 Bedrooms 8 Guests
Sep 14 - 18
$893 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

Seasons Lane Sensation

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 14 - 21
$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.

Huckleberry Hideaway

Sag Harbor, NY, US
7 Bedrooms 14 Guests
Sep 14 - 17
$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.

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.

Bright, Luxe, Country Home with Pool; Near Beach & Village

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 14 - 21
$1,124 night

Please note that a reservation for this property needs to be approved before it is confirmed. Southampton Charm Surrounded by Protective Reserves, Steps to Marina Bay Beach, Golf Courses and Downtown Southampton Village 4BR/3BA, Classic Cedar Shingle Home, Near Bay & Ocean Beaches, Village, & Golf, w/ new patio and built in BBQ/fridge, outdoor shower, pergola lighting Nestled in Southampton lies a professionally decorated, classic Southampton home. The backyard paradise alone makes a statement, while the cedar shingled exterior of the property leaves a touch of familiarity. Southampton Charm truly puts the South in Southampton. The landscape and separate butlers pantry are the proof. The decor is everything one would expect from a charming estate in the countryside. The yard offers shady spots and gorgeous gardens for when youre cooling off from a few laps in the heated pool or for when you have to take a break from being the grill master. As of the end of 2021, the property has a new patio, built in BBQ/fridge, outdoor shower, privacy landscaping, and pergola lighting. Southampton Charm offers four spacious bedrooms and ample common space to spend quality time with friends or family. Eat in the sun-filled dining room around the magnificent dining room table, and finish off the night with an aperitif in the living room with a fire crackling in the background. There are new indoor UV lights and HEPA filters on HVAC system for utmost sanitation as well as a new paneled Thermador refrigerator and updated furniture and dcor! Should you find yourself wanting to further explore, the property is moments away from Marina and Bay Beach in addition to Southampton Village, three major golf clubs, and other ocean beaches. *Pets prohibited unless our express approval is given This property has a max occupancy of 8 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Full Ensuite Bathroom, Streaming TV Bedroom 2: One Queen Bed, First Floor/Main Floor Bedroom 3: One Queen Bed, First Floor/Main Floor, Jack & Jill Ensuite Bathroom Bedroom 4: One Double/Full Bed, First Floor/Main Floor, Jack & Jill Ensuite Bathroom Bathrooms Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower, Tub Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub TVs Bedroom 1: Streaming Outdoors & Pool/Spas Bicycle, Grill (Gas), Deck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Outdoor Shower (Hot + Cold Water), Balcony, Private Pool (Heated) Amenities Usable Fireplace, Air Conditioning, Dryer, Internet (Wifi), Bed Linens, Washer, Hair Dryer, Bath Towels, Living Room, Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Pack 'n Play/Travel Crib, Laptop-Friendly Workspace, Pots and Pans, Stove, Oven, Dishwasher, Microwave, Coffee (Pot), Toaster, Dishes and Silverware, Television (Main Living Room), Parking Suitability: Primary renter must be at least 25 years old. 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. 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.

Stunning Saint Andrews

Southampton, NY, US
5 Bedrooms 10 Guests
Sep 24 - 26
$969 night

Stunning Saint Andrews Newly Renovated, Modern home with pool, cathedral ceilings, open-floor plan, minutes from Southampton Village and ocean beaches! 5BR/4BA - Expansive back deck, cozy fireplace, pool table, work-from-home desk, several seating areas, flooding natural light Located mere minutes from Southampton Village and stunning ocean and bay beaches sits this stunning Post-Modern on a quiet cul-de-sac. Designed with an open-floor plan and private pool, this home is an ideal getaway destination for a group of friends/family. The house, furnished with both elegance and comfort in mind, is warm and welcoming. The light-filled main level includes a large living room with fireplace, dining area, and kitchen with access to the sweeping back deck from multiple entrances. The comfortable furniture, succulents, and accessories create a serene and calming environment. Deeper into the main level, you’ll discover a master suite, one queen bedroom with direct deck access, a twin bedroom, a full bath and a half bath. No matter your culinary skills, the kitchen includes everything one could need to whip up a meal. Topped with Caesarstone and containing several counter height chairs, the island is the perfect place to lay out a few snacks throughout the day, or hors doeuvres prior to the main meal. Feel free to dine at the handsome walnut table set for eight (expandable to 10) or bring the meal right outside onto the deck to enjoy as the sun begins to set. The lower level has a family room with a 77-inch television, pool table, game table, laundry room, full bathroom, a king bedroom, a queen bedroom with Zoom-ready office setup, and access to the garage. Enjoy a game of pool on the stunning table, play board games on the game table or enjoy a good movie while being nuzzled into the Cloud sectional. Out on the deck, you will find an extra-large grill with a direct gas hookup and enough surface area for 28 burgers. The deck also features a large dining table that can seat ten people, outdoor sofas, lounges, and chairs. Stairs lead down to the heated saltwater pool flanked by chaise lounges and umbrellas. Spend the day lounging on the cushioned patio furniture on the deck and taking frequent dips in the sparkling pool to cool off. If, however, you desire to do some sight-seeing, shopping, or dining in local restaurants, the Village of Southampton is only a few minutes away via car. At the end of a fun day, retire to one of the five well-curated bedrooms for a peaceful nights rest, and wake up feeling rejuvenated and ready for the following day of fun in the sun. No matter how you choose to spend your days, Stunning Saint Andrews will surely provide you and your group with a memorable and enjoyable stay. This property has a max occupancy of 10 Bedrooms Master Bedroom: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Front Bedroom: Two Twin Single Beds, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Rear Bedroom: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet, Balcony/Deck Lower Level King: One King Bed, Lower Level, Air Conditioning, Standard Closet Lower Level Office / Queen: One Queen Bed, Lower Level, Air Conditioning, Standard Closet Bathrooms Master Bathroom: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Main Level Powder Room: Half Bath, First Floor/Main Floor, Handicap Accessible Main Level Full Bath: Full Bath, First Floor/Main Floor, Jack & Jill, Shower/Tub Combo Lower Level Full Bath: Full Bath, Lower Level, Shower TVs Master Bedroom: Streaming Front Bedroom: Streaming Rear Bedroom: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (12 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Beach Umbrella, Cooler, Fence Around The Yard, Private Pool (Outdoor, Heated), Hot Tub Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Coffee (Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Game Room, Pool Table, Private Entrance, Parking (6 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Ice Maker, Laptop-Friendly Workspace, Pots and Pans Special Features -Across from the Shinnecock Nature Preserve. Easy hiking paths. -No outside/thru traffic safe streets to walk and bike. -Cul de sac with three homes. Location Nearby Beaches: Meschutt Beach 3.5 miles Cooper’s Beach 4.6 miles Ponquogue Beach 7.9 miles Nearby Grocery Stores: Citarella 3.7 miles Stop & Shop SH 3.6 miles King Kullen HB 4.9 miles Stop & Shop HB 6.0 miles Nearby Restaurants and Bars: Saaz Indian Cuisine Showwin Japanese Cuisine Cowfish Edgewater Restaurant Canal Cafe Sundays on the Bay Rumba Out of the Blue Seafood Shinnecock Lobster Factory Local Burger All Village of Southampton Spots Other Location Information: -4 miles from Village of Southampton Main Street -Shinnecock Nature Preserve across the main road -Shinnecock Hills Golf Club 3 minutes away (by car) Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 3,100 Pool fence can be installed for an additional fee. Suitability: Not handicap accessible. Not suitable for unrelated guests. Primary renter must be at least 30 years old. Pet Policy: One hypoallergenic, non-shedding dog of 50 lbs or less is permitted for an additional $300.00 per booking. Non hypoallergenic/shedding dogs or any 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 $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 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. Open Late April usually. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: Open 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. Pool closed in late October. 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. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. 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.

Meadowood Manor | 6BR Outdoor Spaces

Sag Harbor, NY, US
6 Bedrooms 12 Guests
Sep 28 - Oct 1
$493 night

Welcome to Meadowood Manor, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Experience the best of the Hamptons in style at Meadowood Manor, a luxurious home located in the heart of Sag Harbor. Offering a selection of amenities including a salt water pool, outdoor shower, and a private full basketball/tennis court, guests can relax, unwind, and enjoy the great outdoors. Inside, the open floor concept with an expansive living space and fully-stocked kitchen is perfect for lounging, and 6 luxurious bedrooms provide an idyllic retreat for any group. Conveniently located near Sag Harbor Village and Bridgehampton, as well as a selection of fantastic beaches and restaurants, every amenity you need is at your fingertips for an unforgettable experience. Whether you’re seeking a summer or year-round retreat, Meadowood Manor is the perfect luxury rental property for you. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are allowed at this property for an additional $150 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 bookings at this property are restricted to guests aged 30 and over. Parties are strictly prohibited, and any request to exceed the maximum occupancy will require owner approval. Please note the pool is serviced on Tuesdays during the open season, and both the pool and hot tub are closed during the winter months. Landscaping, seasonal pool maintenance, and pest control maintain periodic service schedules that may take place during your stay. The pool and hot tub are currently closed and will be guest-ready starting May 21, 2026. They are open seasonally and, weather permitting, may remain open through the end of September and potentially into mid-October. Our pool is cleaned and chemically balanced weekly. As an open-air pool, natural debris from wind and breeze are normal between service visits — a skimmer net is available for your convenience. Our team is always happy to assist if needed. 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. The jacuzzi jets in the primary bathroom are not functional. Please note, a required propane fee of $75 per day applies to all stays. Parking Details: Cars can park in the driveway of the property and there is plenty of space for parking. The garage is not accessible. 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 $1,000 as well as possible removal from the property. Security deposit Stays up to 13 nights: $2,500 credit hold Stays between 14 and 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

Summerset Villa | Home w/ Pool

Bridgehampton, NY, US
4 Bedrooms 8 Guests
Sep 14 - 21
$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.

Secluded Contemporary Home in Southampton with Pool

Southampton, NY, US
4 Bedrooms 8 Guests
Oct 1 - 29
$999 night

Hampton Muse New Listing: Live the good life in this perfectly secluded and contemporary home in Southampton! 3BR/2.5BA w/ light-filled living areas, brick fireplace, dining area, wraparound mahogany deck with a heated pool, and more! Live the good life in Southampton! Set on a just-shy acre, this contemporary home is the perfect secluded escape with lots of privacy. Spend your days outside on the massive deck or roaming the expansive yard, as you kick back and enjoy this tranquil retreat. This stylish three-bedroom, two and a half bath contemporary offers 2,089+/- sq. ft. of bright living space. On the first floor, light-filled living areas flow among the living room with floor to ceiling brick fireplace, dining area, and kitchen with stainless steel appliances. Glass doors open to a spacious new wraparound mahogany deck with a heated pool. Also on this level are a serene master bedroom suite and a large den. Two more bedrooms and another full bath are on the second floor. The lower level has laundry and a full bath. Conveniently located close to both Sag Harbor and Southampton Villages, and all the restaurants and shops both have to offer, this home is also within easy reach of ocean beaches. Prepare to fall in love with the Hamptons lifestyle, as you experience it at its very best! This property has a max occupancy of 6 Bedrooms Bedroom 1: One Queen Bed, 1st Floor, Air Conditioning, Ensuite Bathroom, TV, Closet Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, TV, Closet Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, TV, Closet Bathrooms Bathroom 1: Full Bath, 1st Floor, Ensuite, Tub Bathroom 2: Full Bath, 2nd Floor, Jack & Jill, Tub Bathroom 3: Half Bath, 1st Floor TVs Bedroom 1 Bedroom 2 Bedroom 3 Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (10 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Beach Chairs (4 Chairs), Beach Toys, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Wood), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot, Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Electric Vehicle Charger, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 2,100 Suitability: Not suitable for persons with disabilities. Primary renter must be at least 25 years old. Pet Policy: One dog of 25 lbs or less is permitted. Dogs over 25 lbs 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 $1,000.00 per dog will be required. Utility Disclaimer: Normal usage of the following utilities is included in the total booking amount: Pool Heating (if applicable), Pool/Hot-Tub Maintenance (if applicable), Heating Oil/Propane/Natural Gas, Electricity, Cable/TV/Internet/Phone, and Garbage Removal If the cost of utilities exceeds $120.00/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. Additional Persons: Additional persons are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. 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.

Noyac Hills Oasis

Southampton, NY, US
3 Bedrooms 6 Guests
Sep 14 - 27
$1,272 night

Noyac Hills Oasis Southampton Retreat, Spacious Family Escape with Heated Pool & Stunning Outdoor Living 3BR/2BA: Heated Pool, Fence Around The Yard, Outdoor Shower, Paddle Board, Patio, and Gas Grill Set on a quiet, private block in the heart of Southampton, this beautifully designed garden oasis offers a serene escape tailored for effortless family living. From the moment guests arrive, they are welcomed into a thoughtfully curated home where an open floorplan creates a natural sense of connection and ease. Ideal for families, the layout blends shared living spaces with comfortable bedrooms and well-appointed bathrooms, allowing everyone to gather or unwind as they please. Surrounded by lush greenery and set apart from the bustle of everyday life, the home feels like a peaceful sanctuaryperfect for slowing down, reconnecting, and enjoying the simple luxury of time well spent together. Outdoors, the property truly shines as a private oasis designed for both relaxation and recreation. The heated pool invites leisurely mornings and sun-soaked afternoons, while the fully fenced yard ensures a sense of seclusion and comfort. Guests can rinse off in the outdoor shower after a day in the sun or take advantage of the paddle board for tranquil adventures on the water. The patio area is ideal for gathering, whether enjoying a quiet morning coffee or hosting an evening meal fresh off the gas grill. Every detail of the exterior has been crafted to offer total privacy while embracing the beauty of outdoor living. Inside, the home unfolds into a bright and airy living environment filled with natural light. Expansive windows illuminate the open layout, where the living room flows seamlessly into the dining area and gourmet kitchen. Designed with both style and function in mind, the kitchen features top-of-the-line appliances, a coffee maker for slow mornings, and ample space for preparing meals with ease. High-speed WiFi, air conditioning, and a washer and dryer provide modern convenience throughout the stay. The open living spaces encourage effortless movement and connection, making it easy to transition from relaxed lounging to shared meals and memorable conversations. The bedrooms are designed as restful retreats, each offering a calm and inviting atmosphere enhanced by soft, fresh linens and carefully selected furnishings. With three comfortable bedrooms and two well-appointed bathrooms, the home accommodates families with ease, ensuring both privacy and comfort. The bathrooms are stocked with all the essentials, allowing guests to settle in without a second thought. Every space reflects a balance of simplicity and refinement, creating an environment that feels both elevated and welcoming. Ideally located, this Southampton garden retreat places guests just moments from the areas most sought-after attractions. Renowned restaurants, charming boutiques, and vibrant art galleries are all within easy reach, offering endless opportunities to explore and indulge. Nearby golf courses provide scenic outings for enthusiasts, while the pristine beaches of Southampton invite long days by the water. Whether guests are seeking relaxation, adventure, or a blend of both, this home serves as the perfect base for experiencing the very best of the Hamptonsdelivering a stay defined by comfort, privacy, and understated luxury. *Please note that the cost of Propane/Pool Heating is not included, and the guest will be charged based on usage at the conclusion of the rental period, to be pulled from the Refundable Security Deposit. This property has a max occupancy of 6 Bedrooms Bedroom 1: One Queen Bed, First Floor/Main Floor, Air Conditioning, Standard Closet Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One Queen Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Shower/Tub Combo Bathroom 2: Full Bath, 2nd Floor, Shower/Tub Combo TVs Bedroom 3: Streaming Outdoors & Pool/Spas Beach Chairs, Outdoor Shower (Hot + Cold Water), Fence Around The Yard, Fire Pit (Wood-Burning), Deck/Patio (Uncovered), Grill (Gas), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Paddle Board, Private Pool (Heated, Outdoor) Amenities Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Nespresso), Dishes and Silverware, Pots and Pans, Toaster, Blender, Television (Main Living Room), Kitchen, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Laptop-Friendly Workspace, Usable Fireplace (Wood-Burning), Parking, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Smart TV, Privacy (Mostly Private), Private Entrance, Essentials Special Features *Please note that the cost of Propane/Pool Heating is not included, and the guest will be charged based on usage at the conclusion of the rental period, to be pulled from the Refundable Security Deposit. 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: 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 $50.00 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 $1,200 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.

Hampton Classic

Southampton, NY, US
4 Bedrooms 8 Guests
Sep 14 - 18
$671 night

Hampton Classic Huge Backyard, Large Living Room with Dining Area, Large Den with Built-In Shelves 4BR/2BA, Heated Pool, Hot Tub, Fire Pit Smart TVs Enjoy a classic Hamptons getaway at this lovely home, set on nearly a half acre of land. The 1,700+ sq. ft. house features hardwood flooring and spacious rooms. The open plan layout allows the conversation to flow. In the eat-in kitchen, find stainless steel appliances, ample counterspace, a table that seats six, an island with stool seating for two and a pass-through to one of the living spaces. With two living rooms with oversized couches and wall-mounted smart TVs, no one will be fighting over what to watch; one also has a fireplace to warm up cool nights. Large picture window doors open to the backyard bluestone patio which has an outdoor dining space and sitting area with umbrellas. The heated pool and hot tub are perfect for a quick dip and the fire pit is perfect for gathering around on clear, starry nights. With four bedrooms, the house comfortably sleeps six guests. The rooms are very thoughtfully decorated with an eye for minimalist style. This property has a max occupancy of 8 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning Bedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower/Tub Combo Bathroom 2: Full Bath, First Floor/Main Floor, Shower/Tub Combo Outdoors & Pool/Spas Grill (Gas), Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Outdoor Shower (Hot + Cold Water), Fence Around The Yard, Hot Tub, Private Pool (Heated, Outdoor) Amenities Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Internet (Wifi), Bed Linens, Washer, Hair Dryer, Bath Towels, Living Room, Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Essentials, Heating, Stove, Oven, Dishwasher, Microwave, Coffee (Pot), Toaster, Dishes and Silverware, Pots and Pans, Television, Parking (4 Cars In Driveway), Cable TV, Smart TV, Laptop-Friendly Workspace, Pots and Pans Suitability: 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 $125.00 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. 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 & Hot Tub 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.

Vacation Rentals in The Hamptons by Amenities & Features

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near The Hamptons

Saved Home Image
Sign in or join now to view and save the homes you love