luxury houses with pool for rent Wainscott, United States

Beautifully appointed clean and fresh 4 bedroom 4 bath rental in Wainscott available for seasonal or year round use. Oversized windows offer plenty of light along with stone fireplace and stylish comfortable furnishings in the living room. A chef's kitchen and eat in island provide an ideal area for cooking and entertaining with a dining area for more formal dining. A lovely covered terrace overlooks 2 acres of privacy including heated gunite pool, lounging area and enchanting landscape with raised field stone accents . Spacious and private with easy access to the very best of Hamptons' living. EH RR #: 18-2245 Rental Terms: August - Labor Day: $50,000

147 Wainscott Harbor Road presents a stunning retreat designed by the acclaimed architect Robert A.M. Stern. This renovated home, situated on 2.8+/- acres, spans 3,600 SF+/- and offers five bedrooms, three full bathrooms, and one half bath. Its prime location provides effortless access to Bridgehampton, East Hampton, Sag Harbor Villages, and the area's picturesque ocean beaches. Every detail of the home has been crafted for both comfort and style. The first level features inviting spaces for seamless entertaining, including a gracious dining room and a living room anchored by a cozy fireplace. Both rooms open to an expansive screened-in porch with ample seating for relaxing or gathering with guests. The eat-in kitchen is a chef's dream, outfitted with top-of-the-line Viking appliances, a central island, and a sunny breakfast area. The first-floor primary suite is a serene retreat, bathed in natural light from oversized windows. The spa-like primary bathroom includes dual vanities, a freestanding soaking tub, and a separate glass-enclosed shower. Upstairs, four additional bedrooms, two full baths and a bonus space offer beautifully designed interiors and flexible living options. The sprawling grounds include lush, manicured lawns, a large heated gunite pool and spa and a DecoTurf all-weather tennis court. 147 Wainscott Harbor Road nestled in near Sagaponack North is the epitome of refined Hamptons living, blending thoughtfully designed interiors and exceptional outdoor amenities in a premier location. Rental Terms: Two Weeks: $55,000 October: $30,000 Other / Short Term - 5/22/2026 - 6/15/2026: $40,000 September: $40,000 May: $30,000 Winter Season: $10,000 Per Month

Nestled within the coveted Georgica Estates enclave of East Hampton and just moments from the iconic sands of Georgica Beach, this five-bedroom, four-bath residence offers an opportunity to experience one of the Hamptons' most treasured settings with remarkable ease. One of East Hampton's original homes, it carries a sense of history and authenticity that feels increasingly rare. Privately positioned among extraordinary neighboring estates, the property is embraced by mature trees, sweeping lawns, and established gardens, creating a tranquil sanctuary in a premier location. The proximity to Georgica Beach allows for effortless daily rituals - early morning shoreline strolls as the light rises over the Atlantic, spontaneous afternoons by the water, and golden sunset returns as the sky softens into evening. The rhythm of the ocean becomes part of everyday life. Inside, the atmosphere is relaxed and quietly elegant. Sunlight fills the interiors, doors open naturally to the outdoors, and coastal breezes drift through the rooms. The aesthetic is collected and organic - inviting, personal, and uncontrived - offering a refreshing sense of ease. This is a home where sandy towels are draped casually, a place to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. Lovingly maintained and artist-owned, the home carries a soulful presence. Its aesthetic reflects a collected, organic sensibility - layered, personal, and inviting - offering a refreshing alternative to more polished environments. It is a place to exhale, to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. A true Georgica retreat for those who value privacy, proximity to the ocean, and the quiet luxury of simplicity. Available August through September. Rental Terms: August - Labor Day: $80,000 July: $75,000

This spectacular Sagaponack estate offers the best of Hamptons luxury lifestyle. Designed by a renowned interior designer, the graciously appointed interior flows easily to an outdoor living/dining patio, heated gunite pool, hot tub, tennis court, and exquisitely landscaped garden and lawn. The main floor has a living room, great room open to eat-in kitchen, formal dining room, butler's pantry, powder room, and en-suite bedroom. Upstairs has an additional primary suite, and three bedrooms ensuite with a sitting room and three bathrooms. The lower level includes a large luxury bedroom with an excavated, landscaped window well, a den/media room/exercise room and a staff bedroom and bathroom. Amenities include a fully enclosed lot with driveway gate, an attached garage, ample outdoor parking, double laundry room, speaker system, Wi-Fi, and security system. [[Rental Registration # 20251042]] EH RR #: 20251042 Rental Terms: Two Weeks: $120,000 June: $135,000 July: $195,000 June/July: $295,000 Other / Short Term - Year Round: $850,000 Memorial Day - Labor Day: $500,000 August - Labor Day: $225,000

A rare Sagaponack compound, offering 7 bedrooms in total, designed by Val Florio on +/-1.6 acres of curated landscaped grounds. Surrounded by open sky and farmland vistas, the main residence offers sun-filled living spaces, elegant detailing with casual beachy interiors and generous proportions throughout. Gathering rooms open to expansive mahogany decking and manicured lawns, creating a natural flow for summer living. The fully equipped guest cottage provides an additional three bedrooms, ideal for hosting extending family, staff, or friends while maintaining privacy and comfort. The homes are connected through a tunnel in the finished lower level. The heated gunite pool is complimented by a stylish pool pavilion and sunken pickle-ball court. Located across from Wolffer Estate Stables, Sagaponack's premier horse farm, around the corner from Wolffer Vineyard, and close to world class Sagg Main Beach. This compound delivers the ultimate Hamptons experience minutes from the best of Bridgehampton and Sag Harbor. Rental Terms: June: $75,000 Other / Short Term - 10/1/2026 - 4/30/2027: $55,000 July - Labor Day: $300,000 August - Labor Day: $175,000 July: $150,000

Also available August for $150K. Turn South from fabled Parsonage Lane onto a long private driveway that leads to this 1.7 acre property that backs onto 16 acres of agricultural reserve. There are 5 bedrooms and 6.5 baths in this immaculate modern design with plenty of South and West facing patio for outdoor dining and taking in the view of the lawns, gunite pool and pool patio. Just minutes to Town Line ocean beach. Rental Terms: July: $110,000 August - Labor Day: $150,000 July - Labor Day: $250,000 Other / Short Term - August: $125,000

Location! Location! Location! This Modern home is sited on over 1.5 glorious acres south-of-the highway in Sagaponack, and features 6 bedrooms, 7 bathrooms, an open kitchen, dining area and great room with walls of glass allowing for easy access to the backyard. Three car attached garage. Outside, the expansive decks surround the over sized heated gunite pool, and the professionally landscaped property provides the ultimate setting including a fire pit. Located around the corner from the ocean, this home has it all! Rental Terms: Memorial Day - Labor Day: $350,000

Experience summer in this elegant 7-bedroom, 9.5-bath estate set behind tall privets in one of Sagaponack North's most desirable neighborhoods. Spanning approximately 11,000 square feet on the largest fully cleared property on the street, this impressive home offers exceptional privacy, scale, and classic Hamptons living. Manicured grounds feature expansive bluestone terraces, an oversized 20x45 heated pool, spa, and sprawling lawn with ample space for recreation. The setting is both refined and bucolic, bordered by open farmland and a nearby 7-acre horse riding facility, with close proximity to Wolffer Estate Vineyard, Sagaponack Farm Distillery, golf courses, farm stands, and garden nurseries. Inside, 11-foot ceilings highlight the first floor, featuring a grand living room and family room, each with a fireplace and views of the sun-filled backyard. A formal dining room, Bakes & Kropp chef's kitchen with butler's pantry, and breakfast room offer seamless entertaining. The first level also includes a secondary primary suite, an additional en-suite guest bedroom or office, mudroom, laundry, pool bath with sauna, and three-car garage. The second floor features a luxurious primary suite with private terrace, sitting room or office, wet bar, walk-in closets, and a marble bath. Four additional en-suite bedrooms, a mahogany deck, and second laundry complete the upper level. The finished lower level offers a theater, 1,400-bottle handcrafted mahogany wine cellar with tasting room, expansive living and entertaining space, full bath, and additional bonus room. Ideally located just minutes to Bridgehampton, Wainscott, Sag Harbor, and ocean beaches, this timeless Sagaponack estate offers every amenity for an exceptional Hamptons summer. [[Rental Registration # Pending]] Rental Terms: Other / Short Term - 8/1/2026 - 8/8/2026: $40,000 August - Labor Day: $190,000

This unique property exudes beauty and tranquility in best South of the Highway location. Close to Sagaponack beaches this charming 3 bedroom house has never been offered for rent. Situated on 1.16 acres of beautifully landscaped vistas by renowned landscape designer, Edwina Von Gal, overlooking Sagg Pond. Any 2 weeks from June 15 - July 27, 2026 for $40,000 Any 3 weeks from June 15 - July 27, 2026 for $70,000 3 weeks from August 17 - September 8, 2026 for $90,000 2 weeks from August 24- September 8, 2026 for $70,000 5 weeks from August 3 - September 8, 2026 for $160,000 Rental Terms: Two Weeks: $45,000 Other / Short Term - Short-Term: $160,000

Traditional Luxury Getaway Minutes from East Hampton Village & Ocean Beaches Welcome to Handsome Hills, your perfect escape in the Hamptons! This stunning 5-bedroom, 4-bath home is designed for comfort, relaxation, and making unforgettable memories. Nestled in a peaceful neighborhood just minutes from East Hampton Village and the area's best ocean beaches, this home is the perfect retreat for families and friends looking to unwind in style. Inside, You'll Love: A spacious and beautifully decorated interior with plenty of room to spread out. A first-floor primary suite with a private bath and direct access to the outdoor hot tub. A custom eat-in kitchen featuring stainless steel appliances, perfect for cooking up delicious meals. A formal dining room for elegant dinners and special gatherings. A cozy den for quiet reading or morning coffee. A grand living room with a floor-to-ceiling fireplace, perfect for gathering and relaxing. A fully finished lower level with a movie screen, comfy lounge, pool table, bar, poker table, and dart board - entertainment for everyone! Outdoor Living at Its Best: A heated pool and hot tub for ultimate relaxation. A spacious deck with a grilling station and outdoor dining table for alfresco meals. A hammock to soak up the sun or enjoy an afternoon nap. 2 Kayaks to enjoy a paddle on nearby Georgica Pond. A private outdoor shower, perfect after a dip in the pool or a day at the beach. A large fenced-in yard in a quiet, bike-friendly neighborhood. More to Love: A large garage to store bikes, surfboards, and beach gear. Pet-friendly-your well-behaved fur babies are considered! Concierge touch-celebrating a special occasion? Send your pre-ordered items ahead, and we'll set them up before your arrival. Whether you're here to relax, explore, or celebrate, let us welcome you to your home away from home. [[Rental Registration # Pending]] EH RR #: 23-1270 Rental Terms: July - Labor Day: $109,000 July: $59,000 June: $25,000 June/July: $75,000 August - Labor Day: $65,000 Other / Short Term - Weekly: $15,000 Memorial Day - Labor Day: $125,000

Set on 1.11 acres of exquisitely landscaped grounds, this sophisticated post-modern retreat offers a seamless blend of contemporary design and Hamptons elegance. Built in 1995, the single-story residence spans approximately 2,800 square feet and is ideally positioned moments from Bridgehampton and just over a mile to pristine ocean beaches. The outdoor setting is a true sanctuary, featuring a heated pool, beautifully appointed pool house, expansive rolling lawn, and a shaded dining pavilion complete with a barbecue, perfect for effortless summer entertaining. Inside, the home is bathed in natural light, with airy interiors defined by crisp white tones, clean architectural lines, and modern finishes. The main living room centers around a striking brick fireplace, while the open-concept dining area flows seamlessly into a fully updated kitchen designed for both everyday living and hosting. The residence offers4 total bedrooms and 4 full baths, including a luxurious primary suite and a junior primary suite with its own fireplace. Each bathroom is fully renovated in marble, delivering spa-like comfort throughout. Additional amenities include central air conditioning and high-end furnishings, with the home elegantly appointed in all-new pieces from Restoration Hardware. A refined Sagaponack escape offering style, comfort, and proximity to the very best of the Hamptons. [[Rental Registration # RP230701]] EH RR #: RP230701 Rental Terms: September: $22,500 October: $25,000 Memorial Day - Labor Day: $205,000 July - Labor Day: $190,000 April - Labor Day: $215,000 August - Labor Day: $110,000 June: $35,000 Other / Short Term - Year Round: $220,000 July: $95,000

Timeless East Hampton Estate has been recently renovated with old world charm, style, and a true Hampton flare. The 1st floor of the main house features an open living area with fireplace, media room, library/sitting area, formal dining room with fireplace, country kitchen with breakfast nook, fireplace and seating area. The second floor is highlighted by 6 stylish bedrooms and 4 baths. The 3rd floor offers an additional guest bedroom, private office, and an inviting primary suite with ocean views, a drawing room, and fabulous primary bath. The grounds are accented by wrap around porches, an out door grilling station with outdoor fireplace and dining pavilion. The hedged for privacy pool area offers a 2 bedroom guest house, heated gunite pool, another dining pavilion, and lawn areas perfect for the afternoon soccer match. Your vacation will be magical as ocean breezes relax you. Electric Car ready with a 220 voltage outlet, this home is understated perfection. EH RR #: village Rental Terms: Two Weeks: $125,000 Other / Short Term - Weekly: $62,500

Available for US OPEN! Tucked behind a gated drive, this magazine-featured estate offers an exclusive escape for discerning guests. Four expansive king suites provide comfort and privacy, each thoughtfully appointed with high-end furnishings and serene views. The open-concept layout is anchored by a dramatic double-height living room, flowing seamlessly into a newly renovated chef's kitchen and a striking dining area complete with wet bar and wine fridge-perfect for elevated entertaining. Three spa-inspired bathrooms, including two en-suites, blend modern elegance with functionality. Step outside to five exceptionally designed acres with native plantings curated by a world-renowned landscape designer. Enjoy a fully fenced oversized pool and dining area, north-south tennis court with basketball hoop, a wooden playset, two fire pits, an outdoor shower and bathroom, and a 7-person luxury spa-all designed for effortless entertaining or tranquil evenings under the stars. This is more than a rental-it's a private resort experience. *Added Bonus: High Speed Fiber Internet [[Rental Registration # RP251104]] EH RR #: RP251104 Rental Terms: July: $90,000 Two Weeks: $35,000

This pristine newly renovated traditional sits high on a hilltop in Wainscott, which is one of the many stunning features of this incredible rental property. Two-story, shingle style traditional home with 5,000 +/- square feet of living space offers top quality finishes throughout and offers five bedrooms, five and one-half baths, a professional kitchen with a breakfast bar, a family room, a formal dining room, a living room and two fireplaces. Sun or clouds, the entire home is filled with light enhanced by high ceilings throughout most rooms. Outdoors enjoy the new heated pool with retractable cover, a hot tub and spa, 1,800 +/- square feet of new decking and beautiful new landscaping, along with a three-car garage. [[Rental Registration # 23-1305]] EH RR #: 23-1305 Rental Terms: August - Labor Day: $115,000 July - Labor Day: $200,000 Memorial Day - Labor Day: $245,000 September: $18,000 July: $110,000 October: $18,000

Stylish 5-Bedroom Retreat with Pool and Tennis Court in the Heart of Bridgehampton. Close proximity to town and train. Rental Terms: June: $30,000

This Bridgehampton South classic country farmhouse nestled far off the road on a deep flag lot a 1/4 of a mile to town. This charming house is surrounded by hydrangea in a very private .53-acre parcel. A heated salt-water Gunite pool with a sunning level provides for luxurious sunbathing and a private back deck is partially shaded for evening grilling, and dining alfresco. The large custom chef's kitchen is a focal point of the home lined with a custom built-in bar, display cabinets and a restaurant-grade professional 6-burner + grill Viking range, Subzero fridge, and wine/beverage fridge. A ground-floor bedroom and full bath complete the first floor. Upstairs are two extra-large bedrooms, with a shared bath. The lower level has an exterior stair up to the garden. Perfect for an au-pair or private guest suite, there is a bedroom, separate living room with kitchenette, and full bath. The house is a quick bike ride from coffee in town or pop to the ocean along farm field lanes. [[Rental Registration # RP240795]] EH RR #: RP240795 Rental Terms: July: $40,000 August: $45,000 July - Labor Day: $75,000 Other / Short Term - 5/22/2026 - 8/31/2026: $90,000 Memorial Day - Labor Day: $100,000 June/July: $60,000 August - Labor Day: $50,000

Rebuilt in 2000 and maintained to the highest standards, this exquisite Victorian farmhouse is newly available as a first-time rental. Set along one of Bridgehampton's most sought-after corridors, Ocean Road, the property offers immediate access to the best beaches and village amenities. The main residence features 4 exceptionally laid out bedroom suites, multiple living parlors, and 8 fireplaces. Ample entertaining spaces, includes a chef's eat-in kitchen equipped with premium Viking appliances and custom cabinetry, while several bar and kitchenette areas create effortless flow for hosting. Upstairs, the bedroom suites offer generous proportions, walk-in closets, and spa-style baths, with select rooms featuring fireplaces, ceiling fans, and beautiful views of the gardens. Additional living areas include a billiards room, lower-level entertainment room with bar, and wraparound porch. Enter the 1-acre property to beautiful specimen trees, including 5 Japanese Maples. The main house offers outdoor eating area and leads to a stone wall separating it from the heated gunite pool and guest cottage. The fully equipped cottage consists of one bedroom, a separate living room, and outdoor al fresco eating area. Special bonus: one car with beach pass included. Rental Terms: September: $100,000 August: $200,000

Located on an iconic East Hampton Village lane is this incredible home with 5 en-suite bedrooms, plus 2 half baths. Luxe beach vibe decor surrounds you in comfort and style. Open concept living with first floor living room, dining area, centralized cook's kitchen and an oversized den that leads outdoors to secluded grounds with a heated, gunite pool, large patio and an outdoor shower. Upstairs find a spacious primary bedroom with sitting area and a fireplace plus 3 additional en-suite bedrooms. Want more? Head down to the finished lower level for media, recreation, Peloton, free weights, powder room and another en-suite bedroom. This home has all you could want or need for a perfect summer experience! Rental Terms: Memorial Day - Labor Day: $250,000 June: $55,000 August - Labor Day: $110,000 July: $100,000 July - Labor Day: $200,000 Other / Short Term - Year Round: $300,000

Rental Reg. # RP220705 exp. 9/1/24 Also Available: August 16 - September 2 for $250,000 This highly designed new construction--a designer's own home--offers every amenity. The magnificent 11,000+/- sq. ft. estate spans 2+/- lush acres, but feels like it sits on 50 acres, with panoramic reserve views to the West. Enjoy spectacular farm vistas and sunsets every day. It is unique--as the largest and closest field-view estate just outside Bridgehampton Village. The property is a 1/2 mile to some of the Hamptons best restaurants (including Topping Rose, Almond and Pierres), boutiques and shopping. The backyard is nothing short of a resort. The home offers a 50' heated gunite pool, hot tub, and sunken all-weather tennis court. The outdoor terrace stretches the entire length of the house with two covered porches, a state-of-the-art outdoor kitchen, firepit and new outdoor furniture ensuring everyone will relax in comfort. As well, you will be amazed by the thoughtfulness of the interior design. It comes lovingly appointed by Katie White Interiors, replete with gorgeous, hand-selected furniture and artwork that offer elegance, yet a comfortable modern and beachy vibe. The open concept living areas include the living room and great room, eat-in kitchen with Subzero/Wolf appliances (2 full fridge/freezers), a breakfast area, and multiple glass doors that open to an expansive stone terrace and covered porches. There is a highly designed formal dining room, One of the two primary suites is on the first floor (or can be furnished as an enormous office). A mudroom, with laundry and full pool bath round out the first floor. An architectural free-floating modern staircase leads upstairs, where a second luxurious primary suite features a generous balcony with outdoor furniture for lounging any time of day. Four additional ensuite bedrooms, two of which share a large balcony, are also on this level, along with a laundry room. The finished lower level provides large media/recreation space, a gym, and two additional bedrooms. The house has a state-of-the-art sound system and comfort controls. [[Rental Registration # RP220705]] EH RR #: RP220705 Rental Terms: August - Labor Day: $400,000 June/July: $500,000 July - Labor Day: $700,000 Other / Short Term - Year Round: $1,300,000 June: $200,000 July: $350,000

5BR/ 6.5 BA w/ Tennis on 5 + acres with Pool, Hot Tub, Sauna & Basket Ball Court! 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 primary 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, tennis ball machine 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 primary 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 new 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 children's 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 Harbor's Main Street and 7 minutes to East Hampton. [[Rental Registration # RR-25-1159]] EH RR #: RR-25-1159 Rental Terms: Other / Short Term - Year Round: $500,000 Memorial Day - Labor Day: $295,000 July - Labor Day: $225,000 July: $125,000 June: $85,000 August - Labor Day: $135,000