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), 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: 24-417 expires on 3/28/2026.
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 seven (7) 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 $5,000 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.