Vacation rentals in Sag Harbor, NY with a pool

Explore 103 vacation rentals, homes, and villas with pools in Sag Harbor, 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 Sag Harbor

Sandpiper | 4BR Home w/ Heated Pool

Sag Harbor, NY, US
4 Bedrooms 8 Guests
Sep 14 - 17
$1,295 night

Welcome to Sandpiper, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Discover Sandpiper, a refined 4-bedroom, 4-bathroom coastal retreat nestled within Sag Harbor Village. Designed for effortless indoor-outdoor living, this newly constructed home offers over 3,000 square feet of bright, thoughtfully designed living space, complemented by serene water views and private beach access just moments away. The open-concept main level features white oak flooring throughout, a spacious living and dining area, and a chef’s kitchen outfitted with premium Sub-Zero and Wolf appliances, a striking Breccia Calcutta marble island, and a dedicated bar area ideal for entertaining. Outside, the beautifully landscaped backyard is designed for relaxation, featuring a 200-square foot heated gunite pool with elegant Italian marble coping, generous lawn space, and inviting areas for outdoor dining and lounging. The home’s four bedrooms provide comfortable accommodations for families and groups alike, including a luxurious primary suite and an additional en suite bedroom in the finished lower level, which also offers flexible living space for movie nights, games, or quiet retreats. Guests of Azurest enjoy exclusive access to a private bay beach and the rare opportunity to moor a boat in Sag Harbor Bay. Ideally situated near Havens Beach and just minutes from Sag Harbor Village, you’ll have easy access to charming boutiques, acclaimed restaurants, marinas, and everything that makes this historic waterfront destination one of the Hamptons’ most sought-after escapes. Pet Policy: Pets are allowed with owner approval and a one time $150 charge. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. 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. Please note that weekly mid-stay cleans are required. Cleaning during your stay can be arranged upon request with our partner for an additional $200 fee. Cleaning costs will be paid to them directly. 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.

Stunning Contemporary Compound in Sag Harbor with Private Pool and Tennis Court

Sag Harbor, NY, US
5 Bedrooms 12 Guests
Dec 27 - 29
$1,032 night

Merchant Estate Live the good life and escape out east to Sag Harbor/Wainscott! 5BR/ 6.5 BA w/ Tennis on 5 + acres with Pool, Hot Tub & Sauna, open plan living / dining room / Kitchen and so much more! Escape Out East to Sag Harbor! Live the good life on this remarkable, 5.4 acre gated compound. There’s no doubt you’ll fall in love with the Hamptons, as you enjoy a peaceful stay at this private retreat! This stunning contemporary home sleeps 12, with five en-suite bedrooms, including three master suites, one on the first level with a sauna and a private deck. The sun-filled open concept living room features a cathedral ceiling, skylights, a gas-burning fireplace, and an open dining room with French doors leading to a covered porch. The spectacular state of the art kitchen features Subzero and Wolf appliances as well as a miele and nespresso machines. Additional highlights include a fully finished lower level with ping pong and pool tables, office set up and an additional queen pull out bed. You and your guests will love the convenience of the 7 smart TVs, 5 separate Sonos zones inside and a 6th outside, the Mesh wifi system (gigabyte internet) by Optimum, and the Samsung dryer and washer. In the sun-filled study guests will find a fully functioning office setup complete with a laser printer and IMAC computer. Additional features include top of the line mattresses on each of the beds, a peloton bike and brand new furniture throughout. The north wing master suite features a wood burning fireplace, a private study, a jacuzzi tub and a double shower. In the south wing master suite, you will find 20 foot ceilings, a surround sound system, an additional gas burning fireplace, soaking tub and a double rain head shower. Step outside for some fresh air and enjoy beautiful views of the large grounds featuring a heated gunite pool plus a 10 seat hot tub, a secluded and lighted tennis court, with separate covered entertaining space as well as a fire pit area. Guests can enjoy the use of adult and childrens bicycles, beach chairs, a paddleboard and even a kayak. The home is surrounded by miles of nature preserve trail systems and private ponds to discover. Prepare to fall in love with the Hamptons lifestyle, as you experience it at its very best! This property is a 5 minute drive to Sag Harbors Main Street and 7 minutes to East Hampton. This property has a max occupancy of 12 and can accommodate bunk beds for an additional cost. This property has a max occupancy of 12 Bedrooms Bedroom 1 - Master Suite: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 4 - Second Master Suite: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Additional sleeping space: One Sleep Sofa, Lower Level, Air Conditioning Bathrooms Bathroom 1 - Master Suite: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 4 - Second Master Suite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Jack & Jill, Shower Bathroom 6: Full Bath, Lower Level, Shower Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Tennis Court (Private), Fence Around The Yard, Fence Around The Pool, Fire Pit (Wood-Burning), Bicycle (3 Adult Bikes), Beach Chairs (6 Chairs), Beach Umbrella, Kayak/Canoe, Paddle Board, Private Pool (Outdoor, Heated), Hot Tub (Hot Tub Attached to Pool) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace, Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee, Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Ping Pong Table, Private Entrance, Parking, Garage (2 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Pots and Pans, Sauna Special Features A temporary pool fence is available for use upon request. Other FAQ’s Backyard Fenced In: Yes This property requires a Refundable Deposit of 20% of the Total Rate which will cover Security Deposit and Utilities. 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 $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: 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. When the pool is open, a temporary pool fence is available for use upon request. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. 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. 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 $7,500 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. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. 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.

Coves Bay Beauty

Sag Harbor, NY, US
5 Bedrooms 10 Guests
Oct 26 - Nov 2
$641 night

Coves Bay Beauty Modern Coastal Farmhouse style home with a private pool, open-floor plan, grand back deck, located a quick walk/bike to beaches & town 5BR/4BA - Gallery hallway, gas fireplace, chef's kitchen, ample parking, entertainer's patio, Cozy Earth linens, beach cruisers, and more! Perched near Sag Harbor Cove lies this charming, modern coastal farmhouse-style home with a private pool, open-floor plan, and beautiful backyard. Upon entering the home, you will immediately be struck by the bright and airy atmosphere illuminated with natural light. There are two living rooms one with double height ceilings neighboring a dining table comfortably set for ten. Novice and well-seasoned chefs are welcome to cook in the gourmet kitchen that comes with an oversized island, stainless steel appliances, and ample counter space for meal prep or laying out hors doeuvres. During the day, curl up with your favorite book and relax on any one of the loungers adjacent to the glistening pool. Head to one of the nearby beaches a 10 minute walk to Foster Memorial Town Beach and 5 minute drive to Havens Beach you have nothing but wonderful options. As the sun begins to set, hop on a provided beach cruiser and venture into downtown Sag Harbor for sight-seeing, shopping, and renowned local restaurants. Retire to one of the spacious bedrooms for a peaceful nights sleep, or stargaze with a nightcap from the upstairs deck. For unparalleled sleep and leisure, each bed in this property is made with temperature-regulating and luxuriously soft bamboo viscose linens by Cozy Earth. Rest assured, there is plenty of drawer and closet space to completely unpack and settle in. With new coastal furnishings, pool, and wonderful amenities, this Coves Bay Beauty has all the makings for a memorable stay! This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 3: Two Double/Full Beds, 2nd Floor, Air Conditioning, Streaming TV, Walk-in Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Walk-in Closet Bedroom 5: One Queen Bed, First Floor/Main Floor, Air Conditioning, Walk-in Closet Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower Master Bath: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4: Full Bath, 2nd Floor, Shower, Tub TVs Bedroom 1: Streaming Bedroom 2: Streaming Bedroom 3: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Outdoor Shower, Balcony, Bicycle (4 Adult Bikes), Fence Around The Yard, Beach Chairs (4 Chairs), Cooler, Grill (Gas), Beach Umbrella, Beach Toys, Private Pool (Outdoor, Heated, Saltwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Dishwasher, Microwave, Coffee (Pot, Keurig, Other), Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room), Smart TV, Parking (4 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Toaster, Blender, Iron/Ironing Board, Laptop-Friendly Workspace, Pots and Pans, Essentials, Ice Maker, Pack 'n Play/Travel Crib Location Nearby Beaches: Foster Memorial Beach Havens Beach Nearby Grocery Stores: Schiavoni’s Market Cavaniola’s Gourmet Kitchen Provisions Cromer’s Market Nearby Restaurants and Bars: Tutto il Giorno The American Hotel Page at 63 Main Lulu Kitchen & Bar Baron’s Cove Dockside Bar & Grill Grindstone Coffee and Donuts Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 3,250 Rental Registration: 12 expires on 3/19/2027. Suitability: Not handicap accessible. Not suitable for unrelated guests. Primary renter must be at least 30 years old. Pet Policy: One dog of 25 lbs or less is permitted for an additional $500.00 per booking. 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). 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 $110.00 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 $150.00 per person per night may be required. Events Policy: Events are prohibited unless express approval is provided. An event fee of $2,000.00 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. 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.

Beachwood Cove by 3BR w/ Heated Pool

East Hampton, NY, US
3 Bedrooms 6 Guests
Oct 17 - 31
$354 night

Welcome to Beachwood Cove, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. This stunning 3 bedroom, 2.5 bathroom home with a private pool, and a Tesla/EV charger is perfectly located 7 minutes away from Sag Harbor Village and East Hampton Village. Enjoy the perfect indoor/outdoor living experience with over 1700 square feet of outdoor space and 800 square foot pool, with a wrap around deck on the upper floor. There is a spacious living room with treehouse views that leads to an eat-in and dining area with the deck overlooking the pool area. Enjoy the day by the pool, or have a late-night BBQ. This home features a primary bedroom with a king bed and an en-suite bathroom on the upper level, two luxuriously appointed additional bedrooms, one including a queen bed, and the other with 2 double sized beds. Experience unparalleled levels of privacy and convenience with this ideal home - the perfect getaway for your next vacation. To finalize your reservation, all guests must pass a mandatory third-party screening process. Rental Registry Certificate Number: RR-26-167 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. This property requires owner approval for all reservations and completion of a background check, with a minimum 72-hour notice period after booking to confirm the reservation. The pool is open seasonally and will close on October 19, 2026. It is professionally cleaned and chemically balanced weekly; however, as an open-air pool, natural debris between service visits is normal. A skimmer net is provided for your convenience, and our team is always happy to assist if needed. Pool heating is available for an additional $75/night and is kept at a maximum temperature of 80°F under normal operating and weather conditions. Outdoor pool temperatures may vary based on weather, usage, and other external factors. While we make every effort to ensure the heater is functioning properly, pool heating cannot be guaranteed at a specific temperature at all times. In the unlikely event the heater is unavailable due to a mechanical or service issue, pool heating fees will be refunded. Utilities, including pool heating, are billed separately for stays over 14 nights. Landscaping, pool maintenance, and pest control services follow a regular weekly, biweekly, or monthly schedule and may occur during your stay. Wood-burning fireplaces are not permitted for use, and the wine fridge shown in the photos is currently inoperable. Parking Details: Garage for 2 cars with Tesla/EV charger. Workstations: There are multiple desks throughout the home, external monitors and wireless mouse, only 1 keyboard are available for your use. You may also use your own laptop. 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 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

Sag Harbor Estate

Sag Harbor, NY, US
5 Bedrooms 10 Guests
Sep 14 - 16
$3,020 night

Please note that a reservation for this property needs to be approved before it is confirmed. Sag Harbor Estate Stunning Sag Harbor Estate on Over 3 Acres, Pool, Tennis, Perfect for Families 5BR/6BA: private heated pool, hot tub, tennis court, pool table, gym, sundeck, pool house, gas BBQ, outdoor dining, sonos speakers Situated on over three pristine acres in Sag Harbor, this expansive estate offers the ultimate combination of luxury and tranquility. Boasting five bedrooms and six bathrooms, the homes open floorplan is bathed in natural light and designed to inspire relaxation and connection. With a maximum occupancy of 10, this sophisticated retreat is perfect for families or groups seeking an unforgettable escape from the bustle of daily life. Set on a private and picturesque block, the estate offers seamless indoor and outdoor living, inviting you to soak in the beauty of the surrounding landscape. Step into a world of serenity and sophistication as you explore the estates exceptional outdoor amenities. The private heated pool beckons for leisurely swims, while the adjacent hot tub offers a soothing retreat under the stars. Sports enthusiasts will delight in the private tennis court, perfect for a morning match. Expansive decks and a spacious patio provide endless options for al fresco dining and lounging, with a large outdoor dining table, a gas BBQ for grilling, and multiple sitting areas ideal for cocktails and conversation. The lush, manicured yard offers ample space for children to play or for quiet moments of reflection. A well-appointed pool house adds a touch of convenience and luxury, while a sundeck offers the perfect spot to bask in the Hamptons sunshine. With plenty of free parking, this estate ensures that every guest experiences effortless comfort. As you enter the home, you are greeted by a grand, double-height living room, where expansive windows invite natural light to flood the space. The open layout flows effortlessly, connecting the living room, dining room, and gourmet island kitchen. Gather by the inviting fireplaces in the living room, or linger in the state-of-the-art kitchen, equipped with top-of-the-line appliances and a coffee maker for your morning indulgence. Modern conveniences abound, with high-speed WiFi, central air conditioning, and a washer and dryer to meet all your needs. For those working remotely, a dedicated work-from-home space provides the ideal balance of productivity and relaxation. The finished lower level is a hub of entertainment, featuring a full gym, a billiards table, and an additional media area, ensuring that every moment indoors is as engaging as it is comfortable. Each of the five bedrooms offers a serene and private haven, complete with fresh, high-quality linens and plush furnishings. Designed with relaxation in mind, these spacious retreats ensure every guest feels at home. The en-suite bathrooms feature all the essentials for a spa-like experience, providing the perfect place to unwind and refresh after a day of exploring Sag Harbor. This remarkable estate is ideally situated just minutes from the charming village of Sag Harbor. Indulge in the towns vibrant culinary scene, browse its boutique shops and art galleries, or pick up fresh produce from local farm stands. Short Beach, a local favorite, is a stones throw away, offering sun-soaked days and picturesque sunsets. Whether youre seeking a serene escape, a place to connect with loved ones, or a base for exploring the Hamptons, this Sag Harbor estate is a destination in itself. From its elegant interiors to its expansive outdoor amenities, every detail is designed to create a memorable and luxurious experience. This property has a max occupancy of 10 Bedrooms Bedroom 1: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom Primary Bedroom 2: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 4: One King Bed, 2nd Floor, Air Conditioning Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Streaming TV, Walk-in Closet, Balcony/Deck Bathrooms Bathroom 1: Half Bath, First Floor/Main Floor Bathroom 2: Half Bath, First Floor/Main Floor Bathroom 3: Full Bath, First Floor/Main Floor, Ensuite, Tub Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 5: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 6: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 7: Full Bath, Lower Level, Shower TVs Primary Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 5: Streaming Outdoors & Pool/Spas Balcony, Bicycle, Deck/Patio (Covered), Grill (Gas), Tennis Court (Private), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Tennis Equipment (Rackets, Balls), Fence Around The Pool, Fence Around The Yard, Hot Tub (Hot Tub Attached to Pool), Private Pool (Heated, Outdoor, Freshwater) Amenities Bed Linens, Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Gym/Fitness Room (Stationary Bike), Garage, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Pool Table, Speaker System (Sonos), Television (Main Living Room), Private Entrance, Steam Room, Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Smart TV, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Fire Extinguisher, Essentials Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course 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 $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.

Bayside Serene

Sag Harbor, NY, US
3 Bedrooms 6 Guests
Sep 14 - 17
$549 night

Bayside Serene Modern Sag Harbor Escape, Moments from the Water and Long Beach to View Amazing Sunsets, Perfect For Families 3BR/2.5BA: Brand new heated pool, outdoor dining, private yard, chic interiors, close to town and beaches Nestled in the heart of Sag Harbor, this modern and chic home offers the perfect blend of contemporary comfort and coastal charm. Ideally located just steps from the water and a short distance to Sag Harbor’s charming village center, guests will find themselves within easy reach of pristine beaches including Long Beach, renowned restaurants, and boutique shopping. The homes sleek, open floor plan is designed for effortless living, with an abundance of natural light streaming through sliding glass doors that lead directly to the private backyard. Guests will enjoy the luxury of a brand new private pool, promising a serene and exclusive holiday experience. Boasting three well-appointed bedrooms and two and a half baths, this property comfortably accommodates up to six guests, making it the ideal retreat for families or a small group of friends seeking a stylish escape from daily life. Step outside to discover the homes beautifully designed outdoor spaces. The private, tree-lined yard offers a peaceful oasis where guests can relax and unwind. The outdoor deck is the perfect place for enjoying morning coffee or evening cocktails. A covered patio with a dining table invites alfresco dining, whether it’s a casual lunch or a sunset dinner under the stars. The private heated pool is the centerpiece of the expansive yard, where guests can relax or play in seclusion. Thoughtfully landscaped for privacy and tranquility, the yard provides the perfect setting for sunbathing, socializing, or simply soaking in the quiet surroundings. With plenty of free parking available, coming and going is effortlessthough you may find yourself wanting to stay put and savor the laid-back Sag Harbor lifestyle. Inside, the homes modern architecture and chic furnishings create a stylish yet inviting atmosphere. The open-concept living spaces are anchored by a spacious living room with plush seating and large windows that bathe the room in natural light. Sliding glass doors seamlessly connect the living and dining areas to the backyard, creating a smooth indoor-outdoor flow that enhances the sense of space and relaxation. The sleek, fully equipped kitchen serves as the heart of the home, outfitted with state-of-the-art appliances, a coffee maker, and all the cooking essentials needed to prepare meals with ease. A large island provides extra prep space and serves as a natural gathering spot for morning coffee or evening cocktails. High-speed WiFi, central AC, and a washer and dryer ensure every modern convenience is at your fingertips. Upstairs, the three well-appointed bedrooms provide a peaceful and restful retreat. The primary suite features a spacious and bright sitting area with a couch and chairs, and an ensuite bathroom with a modern vanity and walk-in shower. Up the private staircase you’ll find the lofted sleeping area, complete with a king-size bed and large windows. The two additional bedrooms, each designed to comfortably accommodate two adults, share a stylish hall bath with contemporary fixtures and a combination tub and shower. All bedrooms are dressed in crisp, fresh linens and outfitted with thoughtful touches to enhance your stay. A convenient powder room with a washer and dryer is located on the main floor, adding to the homes ease and functionality. This home places you within easy reach of Sag Harbors best attractions. Start your morning with a leisurely stroll to the nearby waters edge, or take a short drive to one of the areas renowned beaches. The vibrant village center is just minutes away, where youll find charming cafes, upscale boutiques, and art galleries showcasing work from local and international artists. Food lovers will appreciate Sag Harbors diverse dining scene, from fresh seafood at The American Hotel to farm-to-table cuisine at Lulu Kitchen & Bar. Golf enthusiasts can enjoy a round at the nearby Noyac Golf Club, while wine lovers will appreciate tastings at Wlffer Estate Vineyard, just a short drive away. Seasonal farm stands offer fresh produce and local specialties, perfect for stocking the kitchen or creating a picnic for a beach day. Many of these attractions are easily accessible by bike or a short walk, allowing you to fully immerse yourself in the laid-back yet refined Sag Harbor lifestyle. This modern Sag Harbor retreat offers the perfect combination of style, comfort, and convenience. Whether youre spending your days lounging by the water, exploring the vibrant local scene, or simply relaxing at home, this chic and thoughtfully designed property provides the ideal backdrop for an unforgettable getaway. This property has a max occupancy of 6 Bedrooms Bedroom 1 - Primary (Loft): One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2 - Guest: One King Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3 - Guest: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bathrooms Bathroom 1 - Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2 - Upstairs Guest: Full Bath, 2nd Floor, Shower/Tub Combo First Floor Powder: Half Bath, First Floor/Main Floor, Handicap Accessible TVs Bedroom 1 - Primary (Loft): Streaming Outdoors & Pool/Spas Deck/Patio (Covered), Patio Furniture (Table, Chairs), Grill (Gas), Lounge Chairs (2 Chairs), Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Air Conditioning, Dryer, Heating, Washer, Hair Dryer, Microwave, Kitchen, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Internet (Wifi), Living Room, Parking, Bath Towels, Dishes and Silverware, Pots and Pans, Television (Main Living Room), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Smart TV, Laptop-Friendly Workspace, Speaker System, Private Entrance, Essentials, Coffee Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Long Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Sag Habor State Golf Course Elizabeth A Morton National Wildlife Refuge 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 $100.00 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. 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.

Hilltop Hideaway

Sag Harbor, NY, US
5 Bedrooms 9 Guests
Sep 14 - 18
$1,190 night

Hilltop Hideaway Expansive Modern Sag Harbor Home with Private Heated Pool, Perfect for Families 4BR/4.5BA plus additional sleeping space: private heated pool, expansive yard, gas fireplace, sunroom, outdoor kitchen and dining with gas BBQ, office Welcome to this expansive Sag Harbor retreat, ideally situated just minutes from the charming villages of Southampton, Sag Harbor, and Bridgehampton. This beautiful home, with its open floor plan, offers four luxurious bedrooms, an additional sleeping space and four and a half pristine bathrooms, comfortably accommodating up to nine guests. As you step inside, you’ll be greeted by a spacious and bright interior, thoughtfully designed with multiple sitting and dining areas perfect for families and gatherings. This is more than just a place to stay; it’s an escape from the hustle and bustle of daily life, nestled on a beautiful private block. Outside, the expansive patio awaits, featuring an outdoor kitchen with a gas BBQ and a delightful dining area. It’s an ideal spot for enjoying al fresco meals and savoring the tranquility of your surroundings. The exterior of this home is a true oasis of relaxation and entertainment. Set on a sprawling acre of land, the property offers total privacy, ensuring a peaceful and secluded stay. The private heated pool is a highlight, inviting you to take a refreshing dip at any time of the day. The expansive patio is designed for outdoor living, with a well-equipped cooking area, a large dining table for memorable meals, and multiple sitting areas perfect for enjoying cocktails or simply soaking in the sun. The yard is spacious, providing plenty of room for outdoor activities and leisurely strolls. Ample free parking is available, making it convenient for all guests to come and go as they please. Step inside and embark on a tour of this stunning home. The open layout is accentuated by an abundance of natural light streaming through large windows, creating a warm and inviting atmosphere. Modern conveniences such as Wi-Fi, a washer and dryer, and central air conditioning are at your disposal, ensuring a comfortable and connected stay. The living spaces flow effortlessly from one to the next, with the living room featuring a cozy gas fireplace and plush seating. The dining room is perfect for family meals, and the gourmet kitchen is a chef’s dream, complete with top-of-the-line appliances, a coffee maker, and ample counter space for preparing delicious dishes. A dedicated work-from-home space and sunroom is also available, catering to guests who need to stay productive during their stay or just need a quite place to relax. The bedrooms in this Sag Harbor home are designed with comfort and tranquility in mind. Fresh linens and all the essentials are provided, ensuring a restful night’s sleep. Each bedroom offers a serene retreat, with ample storage and tasteful decor. The bathrooms are equally impressive, featuring modern fixtures and luxurious amenities. Whether you prefer a refreshing shower or a relaxing soak in the tub, you’ll find everything you need to unwind and rejuvenate. Located close to multiple golf courses, including The Bridge Golf Club, this home is a haven for golf enthusiasts. The beautiful Sag Harbor beaches, such as Foster Memorial Beach, are just a short drive away, offering endless opportunities for sunbathing, swimming, and water sports. The nearby villages of Southampton, Sag Harbor, and Bridgehampton are renowned for their charming restaurants, boutique shops, art galleries, and farm stands, providing plenty of options for dining, shopping, and exploring. Whether you’re looking to immerse yourself in the local culture or simply relax in the comfort of your private retreat, this Sag Harbor home is the perfect choice for your next getaway. This property has a max occupancy of 9 Bedrooms Bedroom 1: One Queen Bed, First Floor/Main Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Double/Full Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Additional Sleeping Space: One Queen Bed, 2nd Floor, Air Conditioning Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 3: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 4: Full Bath, Lower Level, Shower Bathroom 5: Half Bath, First Floor/Main Floor TVs Bedroom 1: Streaming Bedroom 3: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fence Around The Yard, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Private Entrance, Parking, Smoke Detector, Essentials, Wood Stove, Speaker System, Television (Main Living Room), Smart TV, Wine Fridge Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Other FAQ’s Backyard Fenced In: Yes Suitability: Primary renter must be at least 30 years old. Pet Policy: One dog of 25 lbs or less is permitted for an additional $250.00 per booking. 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). 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.

Sag Harbor Grand

Sag Harbor, NY, US
7 Bedrooms 16 Guests
Sep 14 - Oct 12
$6,361 night

Sag Harbor Grand Expansive Sag Harbor Estate, Private Grounds with Stunning Pool & Hot Tub, Perfect for Group Gatherings 7BR/8.5BA: Heated Pool, Hot Tub, Communal Tennis Courts, Ping Pong Table, Pool Table, Gas Gril, Wood Burning Fireplace, and Gym Set on beautifully landscaped private grounds, this expansive Sag Harbor estate offers an exceptional setting for group gatherings, family celebrations, and relaxed coastal living. Thoughtfully designed to balance elegance with comfort, the seven-bedroom, eight-and-a-half-bath residence provides generous space to come together while still offering quiet moments of retreat. Tucked away on a peaceful private block, the home feels like a true escapewhere days unfold slowly, laughter carries easily from room to room, and every detail supports effortless time spent with those who matter most. The outdoor experience is nothing short of spectacular. Surrounded by lush greenery, the private grounds create a serene oasis designed for both relaxation and entertaining. A stunning heated pool serves as the centerpiece of the backyard, inviting guests to swim, lounge, and soak in the sunshine throughout the day. Nearby, a hot tub offers the perfect place to unwind in the evenings, whether after a day at the beach or a friendly tennis match at the communal courts. Multiple outdoor seating areas encourage conversation and connection, while the gas grill makes alfresco dining easy and enjoyable. The propertys sense of privacy allows guests to fully relax, creating a resort-like atmosphere where time seems to slow down. Inside, the home welcomes guests with light-filled interiors and an open, flowing floorplan that immediately feels both grand and inviting. Expansive windows flood the living spaces with natural light, highlighting the homes refined finishes and thoughtful design. The main living areas are perfectly suited for group gatherings, offering comfortable seating, a warm wood-burning fireplace, and an easy transition from living room to dining room and kitchen. Whether hosting a celebratory dinner or enjoying a quiet evening indoors, the spaces feel effortlessly connected and welcoming. The gourmet kitchen is a dream for both casual cooks and experienced hosts. Outfitted with top-of-the-line appliances, generous counter space, and a well-appointed coffee station, it supports everything from leisurely breakfasts to elegant dinners. The kitchen flows seamlessly into the dining area, allowing guests to stay connected while meals are prepared and shared. High-speed WiFi, central air conditioning, and a washer and dryer add everyday convenience, ensuring a comfortable stay no matter the season or length of visit. Entertainment options abound throughout the home. A dedicated game area with a pool table and ping pong table invites friendly competition, while a private gym offers space to maintain fitness routines even while away. These thoughtful amenities ensure there is something for everyone, whether guests are seeking activity or relaxation. The bedrooms are designed as peaceful sanctuaries, offering comfort, privacy, and a sense of retreat. With seven spacious bedrooms spread throughout the home, guests can enjoy restful nights wrapped in fresh, high-quality linens. Each bedroom is paired with a beautifully appointed bathroom, providing spa-like comfort and all the essentials needed for a seamless stay. The abundance of bathrooms ensures ease and convenience for large groups, making mornings and evenings feel unhurried and relaxed. Ideally located in Sag Harbor, this estate places guests within easy reach of the very best the Hamptons have to offer. Renowned restaurants, charming boutiques, art galleries, and cultural attractions are just a short drive away, as are world-class golf courses and the beautiful beaches of Southampton. Whether exploring the village, enjoying waterfront dining, or spending the day by the ocean, guests will find endless opportunities nearbywhile always returning to the tranquility of their private retreat. With its expansive layout, resort-style amenities, and prime Sag Harbor location, this exceptional estate offers an unforgettable setting for gatherings large and small. Designed to inspire connection, comfort, and lasting memories, it is a place where guests can truly settle in, unwind, and experience the Hamptons at its most inviting. This property has a max occupancy of 16 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 2 - Primary: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet, Balcony/Deck Bedroom 5: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Walk-in Closet Bedroom 6: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 7 - Basement: Two Double/Full Beds, Lower Level, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Standard Closet Bathrooms Bathroom 1 - BA 1 Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, First Floor/Main Floor, Shower Bathroom 3 - Primary BR Ensuite: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 4 - BR 3 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 5 - BR 4 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 6 - BR 5 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 7 - BR 6 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 8 - Basement Half Bath: Half Bath, Lower Level Bathroom 9 - Basement Jack and Jill: Full Bath, Lower Level, Ensuite, Shower TVs Bedroom 1: Streaming Bedroom 2 - Primary: Streaming Bedroom 6: Streaming Outdoors & Pool/Spas Balcony, Deck/Patio (Uncovered), Grill (Gas), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Fence Around The Yard, Fire Pit (Wood-Burning), Tennis Court (Communal), Private Pool (Heated, Outdoor, Freshwater), Hot Tub (Hot Tub Attached to Pool) Amenities Bed Linens, Usable Fireplace (Gas-Burning), Air Conditioning (Central Air), Dryer, Internet (Wifi), Washer, Gym/Fitness Room (Elliptical, Stationary Bike, Weight Training Equipment, Stretching / Yoga Mat), Game Room, Garage (Attached, Available for renter cars), Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Other), Dishes and Silverware, Pots and Pans, Toaster, Blender, Ping Pong Table, Pool Table, Speaker System (Bluetooth Speaker), Television (Main Living Room), Private Entrance, Kitchen, Carbon Monoxide Detector, Smoke Detector, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Smart TV, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Privacy (Completely Private), Heating, Hot Water, Essentials Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Suitability: Not handicap accessible. Primary renter must be at least 35 years old. Pet Policy: One dog of 20 lbs or less is permitted. 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. 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: 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.

Sag Harbor Seclusion

Sag Harbor, NY, US
4 Bedrooms 8 Guests
Sep 14 - 27
$1,082 night

Sag Harbor Seclusion Stunning Contemporary Sag Harbor Estate, Minutes to Sag Harbor Village, Perfect for Families 4BR/3.5BA: private heated pool, outdoor shower, fire pit, work out equipment, work-from-home space, speakers, gas BBQ, ping-pong table Revel in luxury amenities, timeless Hampton style and tranquility this Summer at Sag Harbor Seclusion. This entertainers dream of a vacation home offers immaculate outdoor living and a coveted spot along the South Fork. Beautifully fused with classic architectural excellence and chic interior, this enchanting home aims to inspire. Whether youre planning a family gathering or a friend’s gathering, accommodations will exceed your expectations with four bedrooms and 3.5 bathrooms comfortably sleeping up to eight guests. Primely located in one of the most private areas along the South Fork, you are surrounded by Noyac Bay and across the street from Stock Farm preserve. Enjoy kayaking along Ganet Creek or basking in the sun with your favorite book on Foster Memorial beach. Showcased by cool interior tones, open living, sun-splashed spaces and beautiful hardwood flooring, prepare for both full scale entertainment and relaxation. Catch up on work in the dedicated work-from home space, or get your heart pumping in the work out area. Hire a private chef to prepare meals for the home from your designer kitchen boasting top of the line appliances, center island with breakfast bar top, and seamless access to the rear deck. Upstairs, relax into your luxe Primary suite featuring a comfy King bed and private balcony access. Enjoy a soothing bubble bath from your soaking tub in the Primary ensuite bath. Three remaining bedrooms plus two and a half baths complete this home. Outdoors, entertain family and friends from your private backyard oasis equipped with a gorgeous heated pool, ping-pong table, polished landscaping, ample seating and areas to truly relax. Never feel the need to leave this stunning estate as it checks off every box with gas BBQ, outdoor shower, outdoor dining area, and fire pit. Conveniently located along Sag Harbor, you are just minutes from the most beautiful beaches along the East coast plus a vibrant selection of local shopping and dining. Everlasting memories are yours to enjoy at Sag Harbor Seclusion. 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 King Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet, Balcony/Deck Bedroom 4: One Queen Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Additional Sleeping Space: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, Streaming TV, Private (Enclosed) Privacy Bathrooms Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 2: Full Bath, 2nd Floor, Shower Bathroom 3: Full Bath, First Floor/Main Floor, Shower Bathroom 4: Half Bath, First Floor/Main Floor TVs Bedroom 1 Bedroom 3: Streaming Bedroom 4: Streaming Additional Sleeping Space: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Gas), Outdoor Shower (Hot + Cold Water), Tennis Court (Communal), Tennis Equipment (Rackets, Balls), Balcony, Beach Chairs (4 Chairs), Cooler, Fence Around The Yard, Beach Umbrella, Bicycle (2 Adult Bikes), Private Pool (Outdoor, Heated, Saltwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Usable Fireplace (Wood-Burning), Kitchen, Stove, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Coffee (Nespresso, Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Bluetooth Speaker, Stereo), Gym/Fitness Room (Weight Training Equipment, Stretching / Yoga Mat), Ping Pong Table, Parking (3 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Laptop-Friendly Workspace, Pots and Pans Location Nearby Beaches: Foster Memorial Town Beach Sagg Main Beach Ocean Road Beach Nearby Grocery Stores: Sag Harbor Farmer’s Market Schiavoni’s Market Provisions Natural Foods Market Nearby Restaurants and Bars: Murf’s Backstreet Tavern Estia’s Little Kitchen MJ Dowlings Eds Lobster Bar The Dock House Le Bilboquet DOPO La Spiaggia Other Location Information: Elizabeth A Morton National Wildlife Refuge Sag Habor State Golf Course Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: Yes Estimated Square Footage: 2,700 Rental Registration: R-2025-0009 expires on 6/13/2027. Suitability: Not handicap accessible. Primary renter must be at least 30 years old. Pet Policy: One dog of 20 lbs or less is permitted for an additional $350.00 per night. 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 $110.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: 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. 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

Exquisite Home with Tree-lined Yard, Pool & Alfresco Dining

Wainscott, NY, US
5 Bedrooms 10 Guests
Sep 15 - 18
$1,098 night

Wainscott Hideaway Wainscott Southampton Estate Timeless luxury with a private pool, bikes, ping pong, pool table, and plenty of space for friends and family to gather and unwind. 5BR/5.5BA: Classic Southampton Estate in Wainscott with a private pool, bikes, ping pong, pool table, and wine fridge. Nestled in the serene enclave of Wainscott, this classic Southampton estate offers a rare combination of elegance, comfort, and privacy. With 5 bedrooms and 5.5 bathrooms, this luxurious home accommodates up to 10 guests, making it perfect for families, multi-generational gatherings, or groups of friends seeking a sophisticated escape. Located on a beautiful private block, the property is designed as a sanctuary from daily life, where guests can relax, recharge, and enjoy the natural beauty of the Hamptons. Its open floor plan and airy layout create a welcoming environment, effortlessly blending indoor and outdoor living. With easy access to beaches, fine dining, boutique shops, and cultural attractions, this estate provides the perfect balance of peaceful retreat and vibrant local experience. Step outside, and guests are immediately drawn into the estates exceptional exterior amenities. The private pool invites sun-soaked afternoons and leisurely swims, while the surrounding deck and lounge areas offer ideal spaces for entertaining or unwinding with a book. An outdoor shower allows for refreshing rinses after a day at the beach or poolside, and a Bluetooth sound system enhances the ambiance with your favorite tunes. Guests will enjoy exploring the grounds by bike or testing their skills at the ping pong table and pool table, all set within a beautifully landscaped environment that ensures total privacy. Whether relaxing under the sun or enjoying an evening gathering beneath the stars, the outdoor spaces provide the perfect backdrop for unforgettable moments with family and friends. Inside, the homes open layout and abundant natural light create a welcoming, airy atmosphere throughout. The living room, dining area, and gourmet kitchen flow seamlessly together, offering both comfort and sophistication. Guests will appreciate the fully equipped kitchen, featuring top-of-the-line appliances, a coffee maker, and all the essentials needed for creating meals with ease. The living areas are outfitted for relaxation and entertainment, with plush seating, curated dcor, and high-speed Wi-Fi for those who wish to stay connected. Modern conveniences, including central air conditioning, a washer and dryer, and smart technology, ensure a seamless and comfortable stay. Every detail has been carefully considered to create a space that feels both luxurious and inviting. The estates five bedrooms are designed with comfort and serenity in mind. Each bedroom features fresh, high-quality linens, ample storage, and the essentials needed for a restful stay. Bathrooms are modern and well-appointed, offering spa-like touches with plush towels and contemporary fixtures. Whether retreating to a sun-filled bedroom in the morning or enjoying a quiet evening in a serene space, guests will find every room thoughtfully prepared to enhance their experience. The combination of style, function, and attention to detail ensures that each guest enjoys the perfect balance of luxury and ease. Beyond the home, the location of this Wainscott estate offers easy access to the best of the Hamptons lifestyle. Guests can explore charming restaurants serving locally sourced cuisine, boutique shops, and art galleries showcasing regional talent. Golf enthusiasts will find premier courses nearby, while beach lovers can easily reach pristine sands and sparkling waters. The surrounding area is full of cultural and recreational activities, providing endless opportunities for adventure, relaxation, and entertainment. From sunrise walks along the beach to sunset cocktails by the pool, every moment at this estate is designed to create lasting memories. The combination of a luxurious home, exceptional amenities, and a prime location ensures that every stay is a sophisticated and unforgettable escape. This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Ensuite Bathroom, Cable TV, Walk-in Closet Bedroom 2: Two Double/Full Beds, 2nd Floor, Jack & Jill Ensuite Bathroom, Cable TV, Closet Bedroom 3: One Queen Bed, 2nd Floor, Ensuite Bathroom, TV, Closet Bedroom 4: One Queen Bed, 2nd Floor, Ensuite Bathroom, TV, Closet Bedroom 5: One Queen Bed, 2nd Floor Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Shower Master bathroom: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Jack and Jill: Full Bath, 2nd Floor, Ensuite, Jack & Jill, Shower/Tub Combo Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 5: Full Bath, 2nd Floor, Shower Bathroom 6: Half Bath, First Floor/Main Floor TVs Bedroom 1: Cable Bedroom 2: Cable Bedroom 3 Bedroom 4 Outdoors & Pool/Spas Bicycle (3 Adult Bikes), Grill (Gas), Deck/Patio, Lounge Chairs, Patio Furniture, Beach Chairs (4 Chairs), Cooler, Beach Umbrella, Private Pool (Heated) Amenities Usable Fireplace (Wood-Burning), Air Conditioning (Central Air), Dryer, Internet (Wifi), Bed Linens, Washer, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Keurig, Other), Dishes and Silverware, Pots and Pans, Blender, Television, Private Entrance, Kitchen, Essentials, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Cable TV, Ping Pong Table, Pool Table, Garage, Fire Extinguisher, Hair Dryer, Iron/Ironing Board, Heating, Dishwasher, Toaster, Smart TV, Speaker System (Bluetooth Speaker), Electric Vehicle Charger, Wine Fridge, Ice Maker, Laptop-Friendly Workspace, Pots and Pans Special Features Town Water Rental Registration: 26-630 expires on 5/1/2028. Suitability: Primary renter must be at least 30 years old. Pet Policy: One dog of 30 lbs or less is permitted for an additional $200.00 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 $155.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

Northwest Harbor Contemporary

East Hampton, NY, US
4 Bedrooms 8 Guests
Sep 28 - 30
$824 night

Northwest Harbor Contemporary Classic East Hampton Home Perfect for Families Close to Town and Beaches 4BR/3BA: private salt water pool, hot tub, island kitchen, fireplace, marble countertops, multiple sitting areas, office, pool table Welcome to Northwest Harbor Contemporary in East Hampton! This stunning 4 bedroom, 3 bathroom home is the perfect destination for families and friends looking to escape to the Hamptons. As you enter the home, you will be greeted with an open layout, plenty of natural light, and open living spaces. The island kitchen is perfect for preparing meals and entertaining guests, and the dining room table seats 8 people comfortably. The living room features a big screen TV and access to the deck, making it the perfect spot for movie nights or enjoying a glass of wine in the evenings. The double height living room is the perfect spot for lounging with friends and family, and the fireplace adds to the cozy and welcoming atmosphere. The basement even comes equipped with a Peloton, for those who want to stay active during their vacation. Step outside and you will find an array of amenities to enjoy during your stay. Take a dip in the pool, hot tub, or lounge on the chairs while soaking up the sun. The outdoor dining table is perfect for al fresco meals, and the surrounding lush greenery provides a serene and peaceful backdrop. The bedrooms and bathrooms in this home are just as impressive as the rest of the property. The ensuite primary bathroom is beautifully designed and has all the essentials you will need during your stay. The other bathrooms are also well-appointed, ensuring that everyone has a comfortable and relaxing experience. Northwest Harbor Contemporary is located close to art galleries, restaurants, the town center, and the beach, making it the perfect base for exploring all that the Hamptons has to offer. Whether you are looking to relax and unwind or explore and adventure, this property is sure to exceed your expectations. Please note - hot tub is available year-round. No Smoking Policy For the comfort and safety of all guests, smoking is strictly prohibited anywhere on the property, including both indoor and outdoor spaces. Doing such may incur a penalty fee. This property has a max occupancy of 8 Bedrooms Primary Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Guest Bedroom 2: One Double/Full Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Standard Closet Guest Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Guest Bedroom 4: One Queen Bed, 2nd Floor, Air Conditioning, Streaming TV, Standard Closet Additional Sleeping Space: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, Streaming TV Bathrooms Primary Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub Guest Bathroom 2: Full Bath, First Floor/Main Floor, Shower Guest bathroom 3: Full Bath, 2nd Floor, Shower, Tub TVs Primary Bedroom 1: Streaming Guest Bedroom 2: Streaming Guest Bedroom 3: Streaming Guest Bedroom 4: Streaming Additional Sleeping Space: Streaming Outdoors & Pool/Spas Deck/Patio, Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Beach Chairs, Cooler, Fire Pit (Wood-Burning), Fence Around The Pool, Private Pool (Outdoor, Heated, Saltwater), Hot Tub (Freestanding Hot Tub) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Private Entrance, Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Laptop-Friendly Workspace, Television (Main Living Room, Kitchen, Den, Office), Hair Dryer, Parking, Coffee (Pot, Other), Toaster, Blender, Smart TV, Ice Maker, Wine Fridge, Speaker System, Usable Fireplace (Gas-Burning), Pool Table, Privacy (Completely Private) Other FAQ’s Pool Fenced In: Yes Estimated Square Footage: 2,700 Suitability: Not handicap accessible. Primary renter must be at least 25 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 $135.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Hot Tub Disclaimer: April to mid October 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. 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.

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.

Elegant East Hampton

East Hampton, NY, US
5 Bedrooms 12 Guests
Sep 14 - 19
$6,405 night

Elegant East Hampton Spacious East Hampton Luxury Estate with Resort-Style Outdoor Living 5BR/6.5BA: Private pool, pool house, expansive wooden deck, al-fresco dining, elegant interiors Tucked away on 2.5 acres of lush greenery, this luxurious East Hampton estate offers the perfect blend of elegance, seclusion, and resort-style living. From the moment guests arrive, they are welcomed into a private retreat designed for relaxation, connection, and escape from daily life. The property exudes sophistication while remaining warm and inviting, making it an idyllic destination for families, couples, or groups of friends seeking a serene Hamptons getaway. Step outside and the estate unfolds into a private oasis. A heated pool sits at the center of the grounds, surrounded by a paved sundeck, plush chaise loungers, and a stylish pool house equipped with its own bathroom for added convenience. An outdoor shower adds a quintessential Hamptons touch, while the expansive yardenclosed in vibrant greeneryensures total privacy. Just beyond the pool, a large wooden deck flows seamlessly from the homes main living areas, furnished with a plush sectional sofa, a full outdoor dining setup, and a top-of-the-line grill perfect for barbecues under the summer sky. Whether its morning coffee at one of the intimate sitting areas scattered across the grounds, cocktails at sunset, or an afternoon in the shaded screened-in sunroom, every corner of the estate invites relaxation and togetherness. Inside, the home greets guests with light, openness, and understated elegance. A traditional floor plan gives way to thoughtfully designed spaces that balance comfort with luxury. Double-height ceilings and floor-to-ceiling windows fill the home with natural light and frame views of the surrounding trees, creating a constant connection to nature. The main level features a formal living room with elegant furnishings, alongside a cozy den with a plush sofa, fireplace, and flat-screen TVperfect for unwinding after a day at the beach. A spacious kitchen, complete with modern appliances, cookware, and a large central island, is designed for both cooking and entertaining. Just beyond, a formal dining room and multiple sitting areas offer endless opportunities for gathering. Upstairs, a lofted office area provides a quiet work-from-home space, enhanced by serene views of the estates leafy grounds. With central air conditioning, WiFi, and a full laundry setup, every modern comfort is accounted for. The homes five bedrooms are designed as private sanctuaries, each with its own ensuite bathroom. On the main level, the expansive primary suite boasts a king bed, fireplace, and direct access to the deck. Its luxurious ensuite bathroom features a double vanity, soaking tub, and walk-in shower, creating a spa-like retreat. Also on the first floor, a guest suite with a tub/shower combination offers comfort and privacy. Upstairs, three additional bedrooms provide their own unique charmsone with a balcony overlooking the backyard, another with sweeping bay windows, and all with calming, light-filled interiors and curated furnishings. Two powder rooms on the main level and an additional pool house bathroom ensure convenience for larger groups. Fresh linens, plush bedding, and thoughtfully designed details complete the experience of comfort and ease. A fully equipped fitness area is thoughtfully situated in the basement, offering a convenient and well-appointed space for maintaining your wellness routine during your stay. While the estate feels like a secluded destination in itself, it is also ideally situated near the best of East Hampton. Within minutes, guests can explore a vibrant mix of world-class restaurants, stylish boutiques, and charming cafs. Local art galleries and cultural landmarks invite leisurely afternoons, while the areas pristine beachesfamous for their wide stretches of sand and rolling wavesoffer endless opportunities for sunbathing, swimming, or evening walks by the ocean. The estates central location also places it within easy reach of East Hamptons nightlife, wine bars, and seasonal events, ensuring that guests have the perfect balance of privacy and accessibility. This East Hampton estate offers more than just a place to stayit provides an unforgettable Hamptons experience. From its resort-style outdoor living spaces and elegant interiors to its proximity to town, beaches, and cultural attractions, it is a home designed for those who value both sophistication and comfort. Whether gathering with loved ones by the pool, dining under the stars, or simply savoring the peace of the secluded grounds, every stay here is defined by relaxation, connection, and a true sense of escape. This property has a max occupancy of 12 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 - Guest: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Cable Streaming TV, Walk-in Closet Bedroom 3 - Guest: One Double/Full Bed, One Twin Single Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Cable Streaming TV, Walk-in Closet Bedroom 4 - Guest: One Queen Bed, One Sleep Sofa, 2nd Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 5 - Guest: One Queen Bed, One Sleep Sofa, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bathrooms Powder Room 1: Half Bath, First Floor/Main Floor Powder Room 2: Half Bath, First Floor/Main Floor Primary Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bedroom 2 Ensuite: Full Bath, First Floor/Main Floor, Ensuite, Shower Bedroom 3 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bedroom 4 Ensuite: Full Bath, 2nd Floor, Ensuite, Jack & Jill, Shower Bedroom 5 Ensuite: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Pool House Bathroom: Half Bath, Pool House First Floor/Main Floor BASEMENT: Full Bath, Lower Level, Shower TVs Bedroom 1 - Primary: Streaming Bedroom 2 - Guest: Cable and Streaming Bedroom 3 - Guest: Cable and Streaming Bedroom 4 - Guest: Streaming Bedroom 5 - Guest: Streaming Outdoors & Pool/Spas Deck/Patio (Covered), Lounge Chairs, Patio Furniture (Table, Chairs, Umbrella), Grill (Charcoal), Outdoor Shower (Hot + Cold Water), Balcony, Fire Pit (Wood-Burning), Tennis Equipment (Rackets, Balls), Beach Chairs, Beach Umbrella, Cooler, Private Pool (Heated, Saltwater, Outdoor), Hot Tub (Hot Tub Attached to Pool) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning, Heating, Hot Water, Usable Fireplace (Gas-Burning), Kitchen, Stove, Oven, Refrigerator, Ice Maker, Dishwasher, Microwave, Coffee (Keurig, Other), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Laptop-Friendly Workspace, Television (Additional Structure (Pool House, guest house, detached garage)), Smart TV, Parking, Smoke Detector, Fire Extinguisher, Essentials, Privacy (Completely Private), Wine Fridge, Cable TV, Speaker System, Gym/Fitness Room (Treadmill, Stationary Bike, Weight Training Equipment, Stretching / Yoga Mat), Ping Pong Table, Carbon Monoxide Detector Location Nearby Beaches: Main Beach Georgica Beach Wiborg Beach Eqypt Beach Two Mile Hollow Beach Nearby Grocery Stores: Bhumi Farms Iacono Farm Share the Harvest Farm East Hampton IGA Citarella Gourmet Market Stop & Shop Nearby Restaurants and Bars: The Springs Tavern The Leo The 324 Bostwick’s Chowder House The Palm The 1770 House East Hampton Grill Nick & Toni’s Babette’s Maidstone Other Location Information: Cedar Point Country Park East Hampton Village Nature Trail & Wildlife Sanctuary Maidstone Golf Other FAQ’s Backyard Fenced In: Yes Estimated Square Footage: 5,200 Suitability: Not handicap accessible. Primary renter must be at least 25 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 $71.00 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% 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. This property requires a separate booking agreement to be signed by both parties before the reservation is confirmed. Please inquire prior to booking. 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.

Beautiful Bridgehampton Getaway

Bridgehampton, NY, US
5 Bedrooms 10 Guests
Oct 1 - 29
$615 night

Beautiful Bridgehampton Getaway Timeless Hamptons style Beach Home, heated saltwater pool, expansive deck, covered porch, bluestone patio, outdoor kitchen 5BR/5.5BA - with gourmet kitchen, custom wood cabinetry, floor-to-ceiling glass sliding doors leading out to private heated pool Fuel your desire for a lavish Hamptons summer stay at Bridgehampton Getaway. Thoughtfully designed and surrounded by lush landscaping, you will surely enjoy a weekend escape at this classic England-style retreat complete with exceptional outdoor entertainment and amenities. Bring friends and family together to enjoy hot summer days from the large swimming pool or lounging poolside with activities and music. Step inside to discover chic spaces for entertaining including an elegant living room with a fireplace that extends to the rear yard and family room with fireplace. The formal dining room is perfect for intimate dinners or gatherings. The sparkling marble kitchen is well-equipped for meals small or large, with premium appliances. With the ultimate comfort of their guests in mind, there are five spacious bedrooms equipped with fresh, comfy linens and bath essentials including the Primary suite with a fireplace and private balcony. Two additional ensuite guest rooms complete the upper level. The lower level offers additional entertainment with a fully equipped gym, and fifth guest suite with full bath. Outside, enjoy a summer BBQ with friends and family from the stylish outdoor kitchen as you soak up the sun from either the lovely bluestone patio or covered porch with luxe outdoor furniture. Take a splash in the gorgeous heated saltwater pool or picnic from the well-manicured lawns. Take in the beautiful Hamptons weather and all of its glory from the privacy of your own home. Conveniently located between Southampton and East Hampton, enjoy being just moments to the charming Bridgehampton village with a great selection of local shops and eateries including Almond, The Golden Pear Caf, and Citarella. Immerse yourself in the beloved Bridgehampton community, explore the best in dining along the Sag Harbor (just a 5-minute drive) and spend the day at nearby beaches. This property has a max occupancy of 10 Bedrooms Master Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet, Balcony/Deck Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Closet Bedroom 3: One King Bed, Lower Level, Air Conditioning, TV, Closet Bedroom 4: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet Bedroom 5: One Queen Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, TV, Closet Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Shower Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower, Tub Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4: Full Bath, 2nd Floor, Ensuite, Shower/Tub Combo Bathroom 5: Full Bath, Lower Level, Shower Bathroom 6: Half Bath, First Floor/Main Floor TVs Master Bedroom 1 Bedroom 3 Bedroom 4 Bedroom 5 Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Outdoor Shower (Hot + Cold Water), Fence Around The Yard, Beach Chairs, Fire Pit (Gas), Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room, Gym), Private Entrance, Parking (4 Cars In Driveway), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Wine Fridge, Ice Maker, Coffee (Pot, Nespresso), Smart TV, Gym/Fitness Room (Stationary Bike, Weight Training Equipment, Stretching / Yoga Mat), Laptop-Friendly Workspace, Pots and Pans, Speaker System (Sonos) 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: 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 $3,500 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. 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.

Millstone Villa | Home w/ Pool

Sag Harbor, NY, US
7 Bedrooms 14 Guests
Sep 14 - 28
$1,968 night

Welcome to Millstone Villa a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Welcome to Millstone Villa, a refined seven-bedroom, ten bathroom estate nestled on nearly two acres in the heart of Sag Harbor. This cedar and stone residence blends timeless European elegance with clean modern lines, featuring expansive windows that fill the interiors with natural light. A grand entry foyer leads to generous living spaces detailed with custom finishes and premium materials, while the state-of-the-art kitchen is outfitted with Miele appliances, bespoke cabinetry, and a large island perfect for entertaining. Outside, enjoy an infinity-edge pool, private tennis court, and landscaped grounds designed for recreation and relaxation. Located just minutes from Sag Harbor Village, Long Beach, and local wineries, this estate combines sophisticated living with resort-style amenities, offering a rare opportunity to experience the Hamptons at its most elevated. To finalize your reservation, all guests must pass a mandatory third-party screening process. Pet Policy: Pets are not allowed at this property. Property Manager requires a property rental agreement to be signed by the primary guest prior to arrival for all reservations at this home. The pool is open seasonally (2026 Pool closure date: September 28th). It is professionally cleaned and chemically balanced weekly; however, as an open-air pool, natural debris between service visits is normal. A skimmer net is provided for your convenience, and our team is always happy to assist if needed. Pool heating is available for an additional $75/night and is designed to maintain temperatures up to approximately 82–84°F under normal operating and weather conditions. Outdoor pool temperatures may vary based on weather, usage, and other external factors. While we make every effort to ensure the heater is functioning properly, pool heating cannot be guaranteed at a specific temperature at all times. In the unlikely event the heater is unavailable due to a mechanical or service issue, pool heating fees will be refunded. Utilities, including pool heating, are billed separately for stays over 14 nights. The tennis court is now open and available for guest use. 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. Monthly Housekeeping Policy: For all reservations with stays of 60 nights or longer, a full mid-stay cleaning by our housekeeping team is required every 30 days. The required mid-stay cleaning fee(s) will be invoiced immediately prior to the service and upon coordination of a suitable date and time for the cleaning to take place. Security deposit Stays up to 179 nights: $5,000 credit hold Stays of 180 nights or longer: Cash security deposit equal to one month’s rent

Quintessential East Hampton

East Hampton, NY, US
4 Bedrooms 8 Guests
Sep 24 - 27
$1,121 night

Please note that a reservation for this property needs to be approved before it is confirmed. Quintessential East Hampton Spacious East Hampton Retreat Minutes Away from East Hampton Village, Private Pool, Perfect for Families 4BR/3BA: private pool, wood fireplace, work-from-home space, gas BBQ, outdoor dining area, privacy Welcome to your East Hampton sanctuary, a serene retreat nestled just minutes away from East Hampton village and beaches. This exquisite property, featuring 4 bedrooms and 3 bathrooms, accommodates up to 8 guests with ease, making it an ideal getaway for families or small groups seeking an escape from the hustle and bustle of daily life. Set on a beautiful, private block, the home is expertly designed to offer a spacious yet cozy experience with multiple sitting and dining areas, each crafted to enhance your relaxation and comfort. The home’s exterior is as inviting as its interior. Step outside to an expansive patio, a perfect setting for alfresco dining, featuring a large dining table and a gas BBQ. Multiple sitting areas with enough room to seat 13 people, create a delightful environment for evening cocktails or peaceful morning coffees. The centerpiece of the outdoor space is a private pool, offering a refreshing escape on warm summer days. Enjoy the luxury of total privacy and ample free parking, adding convenience to your peaceful stay. Upon entering the home, you’re greeted with an open layout bathed in natural light. The space is designed for comfort and convenience, equipped with WiFi, a washer and dryer, and central air conditioning. The open living spaces flow seamlessly from the living room to the dining room and into the gourmet kitchen, which is a chef’s dream with top-of-the-line appliances and a coffee maker. For those needing a workspace, there’s a dedicated area perfect for working from home. The living room, with its cozy fireplace, offers direct access to the back patio, making indoor-outdoor living effortless. Retire to one of the four beautifully appointed bedrooms, each offering fresh linens and all the essentials needed for a restful night’s sleep. The bathrooms are equally well-equipped, ensuring a comfortable and luxurious experience for all guests. This home is ideally situated just minutes from the charming towns of East Hampton and Amagansett, and fifteen minutes from Sag Harbor when youre ready to explore the local art galleries, savor meals at fine restaurants, and browse through unique shops. If you prefer the ocean, this sanctuary is just ten minutes to the renowned Two-Mile Hollow and Indian Wells Beach, and nearby parks offer a chance to immerse in the natural beauty of the area. This property is not just a vacation rental; it’s a gateway to the best of East Hampton, where every moment becomes a cherished memory. This property has a max occupancy of 8 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, Streaming TV, Standard Closet Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, Standard Closet Bedroom 4: One Double/Full Bed, 2nd Floor, Air Conditioning, Standard Closet Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Shower Bathroom 2: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower, Tub TVs Bedroom 1: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Grill (Gas), Patio Furniture (Table, Chairs), Fence Around The Yard, Lounge Chairs (4 Chairs), Private Pool (Outdoor) Amenities Laptop-Friendly Workspace, Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot), Dishes and Silverware, Pots and Pans, Toaster, Blender, Television (Main Living Room), Kitchen, Carbon Monoxide Detector, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Essentials, Smart TV, Usable Fireplace (Wood-Burning), Private Entrance Location Nearby Beaches: Main Beach Georgica Beach Wiborg Beach Eqypt Beach Two Mile Hollow Beach Indian Wells Beach Nearby Grocery Stores: Bhumi Farms Iacono Farm Share the Harvest Farm East Hampton IGA Citarella Gourmet Market Stop & Shop Nearby Restaurants and Bars: The Springs Tavern The Leo The 324 Bostwick’s Chowder House The Palm The 1770 House East Hampton Grill Nick & Toni’s Babette’s Maidstone Other Location Information: Cedar Point Country Park East Hampton Village Nature Trail & Wildlife Sanctuary Maidstone Golf Other FAQ’s Estimated Square Footage: 2,500 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 $120.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: Additional guests are prohibited unless express approval is provided. Events Policy: Events are prohibited unless express approval is provided. Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

East Hampton Solitude

East Hampton, NY, US
3 Bedrooms 6 Guests
Sep 14 - 16
$641 night

Please note that a reservation for this property needs to be approved before it is confirmed. East Hampton Solitude Expansive East Hampton Home, Centrally Located, Pool & Tennis, Great for Families 3BR/2.5BA: private heated pool, private tennis court, outdoor shower, fire pit, outdoor dining, gas BBQ, sunroom, work-from-home space Welcome to an extraordinary escape in the heart of East Hampton, where style, comfort, and convenience come together to create the ultimate luxury retreat. This spacious and modern home is ideally located close to multiple beaches, offering the perfect blend of coastal charm and sophisticated living. Designed with families in mind, this stunning three-bedroom, two-and-a-half-bathroom property accommodates up to six guests and features a bright, open floor plan with chic dcor throughout. Expansive indoor and outdoor spaces provide ample room to relax and connect, making this home an idyllic sanctuary for those seeking to escape the demands of daily life. Nestled on a beautiful private block, this retreat invites you to unwind in tranquility while staying just moments away from all that East Hampton has to offer. Step outside, and youll discover a true oasis of outdoor living. The private grounds are thoughtfully designed to offer both relaxation and recreation. The expansive outdoor dining area, complete with a gas BBQ, is perfect for hosting memorable meals under the stars. Multiple sitting areas invite you to sip cocktails, share stories, or simply enjoy the peaceful surroundings. The yard offers plenty of space for play and leisure, while the fire pit provides a cozy spot for evenings spent under the stars. The heated private pool is an undeniable highlight, offering a refreshing retreat on warm summer days, and the private tennis court invites you to indulge in a friendly match or two. After a day of activities, rinse off in the outdoor shower and bask in the serene ambiance of this secluded haven. Inside, the home welcomes you with an open layout designed to maximize natural light and foster a sense of connection. The living room, anchored by a stylish fireplace, provides a warm and inviting space to unwind. Adjacent to the living area, the dining room flows effortlessly into the gourmet kitchen, equipped with an array of appliances, a coffee maker, and all the essentials for preparing delicious meals. High ceilings and modern finishes create a bright and airy atmosphere, while the sunroom offers an additional space to relax with a good book or enjoy morning coffee. With WiFi, a dedicated work-from-home area, and central air conditioning, this home seamlessly blends luxury and practicality. A washer and dryer are also available for your convenience. The bedrooms are designed with both comfort and elegance in mind, ensuring restful nights for every guest. Fresh linens and plush bedding adorn each room, while thoughtful touches add to the inviting ambiance. The primary suite features a private ensuite bathroom and ample storage, while the additional bedrooms provide stylish and cozy accommodations for family or friends. The bathrooms are stocked with fluffy towels and all the essentials needed to make your stay as comfortable as possible. Located just minutes from East Hamptons finest attractions, this home places you at the heart of it all. Explore the vibrant local scene, including upscale restaurants, charming shops, and world-class art galleries. Visit the bustling farmers markets to discover fresh, local produce, or spend a day on the greens at nearby golf courses. For a change of pace, Sag Harbors quaint streets and waterfront views are just a short drive away. Whether youre strolling the pristine beaches, indulging in fine dining, or soaking up the areas rich culture, this luxurious retreat offers an unparalleled gateway to the best of the Hamptons. From its thoughtfully designed interiors to its exceptional outdoor amenities, this East Hampton home promises an unforgettable experience for sophisticated travelers. Come and create lasting memories in this exquisite retreatyour perfect getaway awaits. Please note: The fireplace is not available for use from May through September. Any attempt to operate it during this period may result in a fine. This property has a max occupancy of 6 Bedrooms Bedroom 1: Two Double/Full Beds, First Floor/Main Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Standard Closet Bedroom 2: One Queen Bed, First Floor/Main Floor, Air Conditioning, Full Jack & Jill Ensuite Bathroom, Standard Closet, Balcony/Deck Primary Bedroom 3: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bathrooms Bathroom 1: Full Bath, First Floor/Main Floor, Ensuite, Jack & Jill, Shower/Tub Combo Bathroom 2: Half Bath, First Floor/Main Floor Bathroom 3 Primary: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub TVs Primary Bedroom 3: Streaming Outdoors & Pool/Spas Deck/Patio (Uncovered), Grill (Gas), Tennis Court (Private), Outdoor Shower (Hot + Cold Water), Patio Furniture (Table, Chairs, Umbrella), Tennis Equipment (Rackets, Balls), Fence Around The Pool, Fire Pit (Wood-Burning), Lounge Chairs (6 Chairs), Beach Umbrella, Cooler, Beach Chairs, Private Pool (Outdoor, Freshwater, Heated) Amenities Bed Linens, Air Conditioning (Central Air), Dryer, Heating, Internet (Wifi), Washer, Hair Dryer, Iron/Ironing Board, Living Room, Parking, Bath Towels, Pool/Beach Towels, Microwave, Coffee (Pot, Keurig), Dishes and Silverware, Pots and Pans, Toaster, Television (Main Living Room, Kitchen), Private Entrance, Kitchen, Smoke Detector, Hot Water, Refrigerator, Oven, Stove, Dishwasher, Fire Extinguisher, Essentials, Smart TV, Wine Fridge, Laptop-Friendly Workspace, Blender, Ice Maker, Usable Fireplace (Wood-Burning), Carbon Monoxide Detector Location Nearby Beaches: Main Beach Georgica Beach Wiborg Beach Eqypt Beach Two Mile Hollow Beach Nearby Grocery Stores: Bhumi Farms Iacono Farm Share the Harvest Farm East Hampton IGA Citarella Gourmet Market Stop & Shop Nearby Restaurants and Bars: The Springs Tavern The Leo The 324 Bostwick’s Chowder House The Palm The 1770 House East Hampton Grill Nick & Toni’s Babette’s Maidstone Other Location Information: Cedar Point Country Park East Hampton Village Nature Trail & Wildlife Sanctuary Maidstone Golf Other FAQ’s Pool Fenced In: Yes Backyard Fenced In: No Estimated Square Footage: 2,400 Rental Registration: 25-292 expires on 3/14/2027. 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 $100.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only will be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

North Bay Estate | Luxe Villa w/ Pool

East Hampton, NY, US
5 Bedrooms 8 Guests
Sep 14 - 21
$1,572 night

Welcome to North Bay Estate, a Property Manager Home! Property Manager offers beautifully designed residences with the quality and care of a 5-star hotel. Escape to North Bay Estate, a modern Hamptons retreat where elegance meets coastal charm. This architect-designed villa features spacious living areas and 5 luxurious bedrooms, blending contemporary design with warm, airy interiors flooded with natural light. Relax by the private pool, soak up the sun on the terrace, or enjoy serene views of North Bay just steps away. The fully equipped gourmet kitchen, high-end finishes, and designer furnishings make every stay effortless, stylish, and comfortable. Whether you’re entertaining guests or enjoying quiet downtime, this villa provides the perfect backdrop. Ideal for families, friends, or executives seeking privacy and sophistication, it offers the ultimate East Hampton experience, just minutes from pristine beaches, fine dining, local boutiques, and scenic outdoor activities. Your luxurious Hamptons getaway begins here—an unforgettable blend of modern design, coastal serenity, and timeless elegance. Rental Registration No. RR-26-653 Pet Policy: Pets are not allowed If you want the pool heated during your stay, there is an additional $200/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 $10,000 as well as possible removal from the property. A complimentary light weekly touch-up clean is included in the rate. Security deposit A refundable credit card hold of $5,000 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. License number: RR-26-653

East Hampton Exquisite

East Hampton, NY, US
6 Bedrooms 12 Guests
Sep 14 - 18
$2,501 night

East Hampton Exquisite Timeless East Hampton retreat with amazing outdoor space, heated pool, wide sun deck, multiple lounge areas, balcony, firepit, gas grill and minutes to Hampton beaches and village 6BR/6BA - entertainers home, airy floor plan, Sonos sound system, 8 Smart TVs, billiards table, game room with wet bar, Peloton bike, Chefs kitchen, two Primary suites, and all bedrooms outfitted with Cozy Earth linens Where modern elegance, unmatched amenities, and location happily wed. Welcome to East Hampton Exquisite for your next vacation getaway. Located in the heart of East Hampton, enjoy the very best of living along the South Fork. You are just 4 minutes from the town of East Hampton and village with a great selection of local shops and fine dining plus the picturesque nearby beaches including Main, Egypt, and Georgica. Beautifully renovated, this elegant home with exceptional outdoor space makes for a true entertainers delights. Accommodating up 12 guests comfortably, plan an extended family retreat or couples trip packed with activities for fun in the sun. The commanding exterior matches a stunning white interior extending the ultimate welcome. Turn up your favorite summer playlist from the Sonos sound system and let the games begin. Inside, the spacious, two-story Great room offers an airy floor plan for everyone to enjoy. Features include brand new furniture, extra high ceilings, and a new 75" Sony TVs to catch the game on. Grab fresh produce and groceries from Citarella to whip up delicious meals in your Chefs kitchen with a large center island, top of the line Wolf appliances and Sub-Zero Refrigerator, Ninja Bullet and coffeemaker plus a separate dining area. Access to the pool sits just off the kitchen, perfect for dining alfresco-style. Rest and relaxation is of the utmost importance on vacation. Find your place from one of the six serene bedrooms including two Primary ensuite bedrooms, and four bedrooms with two that are ensuite. For unparalleled sleep and leisure, each bed in this property is made with temperature-regulating and luxuriously soft bamboo viscose linens by Cozy Earth. Upstairs, a spacious second living area connects three of the bedrooms with closets and large TVs while overlooking the gorgeous backyard and pool. Ensuring your comfort, new mattresses with covers, down comforters, pillows and sheets have been provided. The lower level offers additional entertainment with a pool table, wet bar, gym and more. Head outside to your private retreat as your expansive backyard boasts a wide sun deck, stunning 20’ x 40’ heated pool, and plenty of lounge seating with a fire pit area. Memories to last a lifetime are yours at East Hampton Exquisite. This property has a max occupancy of 12 Bedrooms Bedroom 1: One King Bed, First Floor/Main Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Standard Closet, Balcony/Deck Bedroom 2: One King Bed, First Floor/Main Floor, Air Conditioning, Streaming TV, Walk-in Closet Bedroom 3: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 4: One King Bed, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet, Balcony/Deck Bedroom 5: Two Double/Full Beds, 2nd Floor, Air Conditioning, Full Ensuite Bathroom, Streaming TV, Walk-in Closet Bedroom 6: Two Double/Full Beds, Lower Level, Air Conditioning, Streaming TV, Standard Closet Bathrooms Bathroom 1: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 2: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 3: Full Bath, 2nd Floor, Ensuite, Shower Bathroom 4: Full Bath, First Floor/Main Floor, Shower Bathroom 5: Full Bath, Lower Level, Shower Bathroom 6: Full Bath, First Floor/Main Floor, Ensuite, Shower, Tub TVs Bedroom 1: Streaming Bedroom 2: Streaming Bedroom 3: Streaming Bedroom 4: Streaming Bedroom 5: Streaming Bedroom 6: Streaming Outdoors & Pool/Spas Deck/Patio, Lounge Chairs (6 Chairs), Patio Furniture (Table, Chairs, Umbrella), Grill (Gas), Fire Pit (Wood-Burning), Outdoor Shower (Hot + Cold Water), Balcony, Beach Chairs (4 Chairs), Beach Umbrella, Cooler, Fence Around The Yard, Bicycle (2 Adult Bikes), Private Pool (Outdoor, Heated, Freshwater) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Hair Dryer, Iron/Ironing Board, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Oven, Refrigerator, Wine Fridge, Ice Maker, Dishwasher, Microwave, Coffee (Pot), Toaster, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television, Smart TV, Speaker System (Sonos), Gym/Fitness Room (Stationary Bike, Stretching / Yoga Mat), Game Room, Pool Table, Private Entrance, Parking (6 Cars In Driveway), Garage (1 Cars In Garage), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Stove, Laptop-Friendly Workspace, Pots and Pans Location Nearby Beaches: Egypt beach, Main beach, Two Mile Hollow Beach, Georgica beach, Wiborg Beach, Sag Harbor Nearby Grocery Stores: IGA, Stop & Shop, Citarella Nearby Restaurants and Bars: Nick & Tonis, EH Grill, The Palm, Bostwicks, Maidstone, 1770 House, John Papa’s, Golden Pear, SiSi Mediterranean, Topping Rose House Other Location Information: Centrally located near town, Sag Harbor in Hansom Heights Other FAQ’s Pool Fenced In: No Backyard Fenced In: Yes Estimated Square Footage: 4,550 Suitability: Not handicap accessible. Not suitable for unrelated guests. 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 $140.00 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. 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.

Cape Lane - Stunning Modern Home with Pool

East Hampton, NY, US
4 Bedrooms 8 Guests
Sep 14 - 28
$543 night

Welcome to Cape Lane, an elegant East Hampton escape where impeccable design and thoughtfully curated decor is sure to impress even the most discerning guests. This modern gem features 4 bedrooms, 2 bathrooms and sleek design. Outside, enjoy the pool, firepit, hammock, and an outdoor shower. Explore East Hampton Town(10 min) and beaches: Sammys Beach(5 min), Maidstone Park Beach(15 min) Cape Lane offers a peaceful retreat with easy access to the charm and beauty of the Hamptons. Cape Lane is located on one of the most serene streets in the East Hampton Northwest Woods, backing a nature preserve ensuring the utmost privacy. This 2,000 sq ft modern marvel offers a tranquil retreat just a short drive from white-sandy beaches. Step inside this modern masterpiece to find yourself enveloped in sophisticated design. The beautiful living room is bright and inviting, courtesy of large windows and doors that fill the room with natural light and frame views of the lush surroundings. Sink into the plush couch, bask in the warmth of the fireplace and enjoy cozy movie nights and leisurely afternoon hangouts. For more quiet relaxation, choose to immerse yourself in your favorite book from the fully stocked bookshelf. Adjacent, the gourmet kitchen awaits, fully equipped with modern appliances and pristine countertops. Prepare delicious meals with ease, surrounded by the sleek elegance of the contemporary design. The indoor dining table provides an elegant setting to enjoy delicious meals together with loved ones. Retreat to the privacy of the four beautifully appointed bedrooms, each thoughtfully designed to ensure a restful night’s sleep. Two bedrooms feature large king-sized beds, a third bedroom boasts a queen-sized bed, while the fourth bedroom is perfect for little ones with full-sized bunk beds. Venture outdoors to discover your own private oasis, where endless possibilities for relaxation and recreation await. Take a refreshing dip in the large pool, soak up the sun on plush loungers, or sway gently in the hammock. As evening falls, gather around the crackling firepit, where laughter and cherished moments are shared under the starlit sky. At Cape Lane, every detail has been carefully crafted to exceed your expectations and create memories to last a lifetime. Whether you’re seeking a tranquil retreat or a vibrant gathering place, this luxurious home offers the perfect blend of elegance, comfort, and sophistication. Cape Lane is just over 2 hours from New York City, and you’ll definitely want a car to get enjoy the region. In the winter, we recommend a car with four-wheel drive that can handle the snow and gravel roads. There is plenty of parking on the premises. *Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates. License number: HMT24-00283

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 Serenity in East Hampton

East Hampton, NY, US
3 Bedrooms 10 Guests
Sep 21 - 24
$732 night

Please note that a reservation for this property needs to be approved before it is confirmed. The Majestic Newly renovated and refurnished, secluded East Hampton home with heated pool, walking to town and 2 miles from the beach 3BR/2.5BA-open living room, Deck/Patio, Lounge Chairs, Patio Furniture, Grill, Private Heated Pool Welcome to your dream vacation rental in East Hampton! This charming 3-bedroom, 2.5-bathroom home is the perfect getaway for those seeking a relaxing and enjoyable stay close to East Hampton Village. Whether you’re in the mood for adventurous activities or leisurely indulgence, this property offers it all. Start your day with a serene paddleboarding session at the local ocean beaches or explore the vibrant shops and eateries nearby. For a peaceful morning, you can meditate on the back patio while surrounded by the beauty of nature. The large open living room provides a cozy space to unwind, and the dining room is ideal for savoring delicious meals. In the evening, why not plan a fun-filled swimming and entertaining session in the generously-sized sunroom, conveniently located just off the heated 20x40 gunite pool? It’s the perfect spot to create unforgettable memories with your loved ones. Step inside this beautifully renovated home and experience classic Hamptons charm at its finest. A professional interior designer has meticulously curated every detail, ensuring a clean aesthetic that still feels warm and inviting for the entire family. You’ll have plenty of space to spread out and relax, with the sunroom and bonus attic space providing additional areas to unwind. The backyard is perfect for some fun yard games and offers a fantastic opportunity to bask in the sun. Every bedroom comes equipped with its own TV, ensuring that everyone in your group can enjoy their favorite shows and movies in privacy. This vacation rental property in East Hampton is waiting for you to experience a getaway like no other, where you can fully embrace the essence of luxury and relaxation. Your unforgettable vacation awaits! This property has a max occupancy of 10 Bedrooms Bedroom 1: One King Bed, 2nd Floor, Air Conditioning, Ensuite Bathroom, TV, Standard Closet Bedroom 2: One Queen Bed, 2nd Floor, Air Conditioning, TV, Closet Bedroom 3: One Queen Bed, 2nd Floor, Air Conditioning, TV, Closet Additional Sleep Space: One Sleep Sofa, First Floor/Main Floor, Air Conditioning, TV Additional Sleeping Space - Attic: Two Twin Single Beds, 3rd Floor, Air Conditioning Bathrooms Bathroom 1: Full Bath, 2nd Floor, Shower/Tub Combo Bathroom 2: Half Bath, First Floor/Main Floor Primary En Suite: Full Bath, 2nd Floor, Ensuite, Shower TVs Bedroom 1 Bedroom 2 Bedroom 3 Additional Sleep Space Outdoors & Pool/Spas Deck/Patio (Uncovered), Lounge Chairs (4 Chairs), Patio Furniture (Table, Chairs), Grill (Gas), Beach Chairs (4 Chairs), Beach Umbrella, Cooler, Fence Around The Yard, Fence Around The Pool, Private Pool (Outdoor, Heated) Amenities Bed Linens, Bath Towels, Pool/Beach Towels, Washer, Dryer, Air Conditioning (Central Air), Heating, Hot Water, Kitchen, Stove, Oven, Refrigerator, Dishwasher, Microwave, Blender, Dishes and Silverware, Pots and Pans, Living Room, Internet (Wifi), Television (Main Living Room, Den), Private Entrance, Parking (3 Cars In Driveway), Carbon Monoxide Detector, Smoke Detector, Fire Extinguisher, Essentials, Ice Maker, Coffee (Keurig), Toaster, Laptop-Friendly Workspace Other FAQ’s Estimated Square Footage: 1,800 Suitability: Not handicap accessible. Primary renter must be at least 25 years old. Pet Policy: Pets are strictly prohibited at this property. Utility Disclaimer: Utility fees are included in the total rental amount. The guest shall be responsible for the costs associated with excessive usage of utilities during the term of the reservation. Excessive usage is defined as utility costs over $135.00 per night of the reservation. Cleaning Disclaimer: One light cleaning per every eight (8) nights booked, and one end of stay cleaning is included in the reservation total. Guests may request additional cleanings at their expense. Additional Guests: No additional guests beyond the max occupancy of this listing are permitted. Events Policy: Events are prohibited Special Use Policy: Reservations that involve hosting events (small or large), commercial activities, or other non-traditional uses -- including rotating groups of guests during the same stay -- require prior written approval from the host. Additional fees and/or an increased security deposit may be imposed. Pool Disclaimer: Due to the climate of the northeastern U.S., outdoor pools and attached hot tubs will typically only be available for use from Memorial Day to Labor Day. If your booking falls outside of that time frame and you intend to use the pool/hot tub, please be sure to inquire if they will be available for use prior to booking. For energy conservation purposes, the pool heater may only be operational from 8am to 6pm. Off-Season Disclaimer: It is typical that spring cleanings and updates do not take place until late April / early May. If your booking falls outside of Memorial Day to Labor Day, please inquire as to whether or not outdoor furniture and equipment will be available for use prior to booking. Payment/Refund Policy: Unless otherwise stated on the property listing, all payments are non-refundable, however, should the guest elect to cancel its reservation, Property Manager will use best efforts to work with the owner of the property to reopen the dates of the reservation in attempt to re-book the property (please note the decision to reopen dates is the owners’). Should Property Manager be successful in re-booking the property for the original dates at the same or higher price than the original reservation, a refund less a 20% penalty, calculated as 20% on the total reservation amount, will be issued to the guest once payment is collected in full for the new reservation. If a new reservation is not made, the guest may use the property for the dates of its original reservation so long as payments have been made in accordance with the payment schedule established at the time of booking and Property Manager is notified in writing 72 hours or more prior to the start of the reservation. Security Deposit Disclaimer: Although rare, accidental damage does happen during a stay. In lieu of a security deposit, guests can rest easy knowing that this property is covered with up to $25,000 of damage protection. Coverage details are provided in the booking agreement. The guest experience for this property is managed by Property Manager, a local vacation rental management company. By booking this property, you will receive a dedicated "Guest Experience Manager" who can help facilitate any request, from grocery shopping to organizing a private chef. You will also have access to 24/7 support that can assist with any question that might arise during your stay. It is important to note that any maintenance tasks are performed by the owner of this property. Showings: To ensure the continued availability and quality of our properties, the owner may need to show the property to prospective renters or buyers. We strive to respect your privacy and provide advance notice and will make every effort to schedule these showings during reasonable daytime hours. We appreciate your understanding and cooperation.

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.

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Vacation Rentals Near Sag Harbor

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