luxury houses with terrace for rent Wainscott, United States

Overlooking 55+/- acres of west-facing reserve on Erica's Lane deep in Sagaponack South minutes from the ocean, this stylish 4-bedroom shingled traditional features a newly updated kitchen and bathrooms, new heated, gunite pool with gleaming white surround, Har-Tru tennis court, fire pit with Adirondack chairs, and playset. Central A/C, Sonos, cable, Wifi, HDTVs, 3 sets of washer/dryer, 2 additional full-size refrigerators and wine fridge. Rental Terms: August - Labor Day: $160,000 July: $140,000 Memorial Day - Labor Day: $350,000 June/July: $190,000 September: $50,000 June: $50,000 Other / Short Term - 8/1/2027 - 9/30/2027: $200,000 July - Labor Day: $300,000

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

Spend your summer in style at Georgica Estates, East Hampton's premier condo community where each unit is a freestanding home offering the privacy and comfort of a single-family residence. Only 10 minutes to Sag Harbor Village & Bridgehampton, this light-filled 4-bedroom, 3.5-bath townhouse is set among nearly 8 beautifully landscaped acres and features an open, airy floor plan perfect for summer living. The first-floor primary suite offers convenience and privacy, while the second level provides three spacious guest bedrooms. With high ceilings, large windows, and sun-drenched living spaces, this home feels bright, cheery, and welcoming. Enjoy cooking in a modern open kitchen with quartz countertops, and stainless steel appliances, and entertain on the private wood deck with a large awning, surrounded by lush gardens and greenery. Other features include hardwood and ceramic tile floors, central air, washer/dryer, fireplace, and a 1-car attached garage. Community amenities are top-tier and meticulously maintained, including: A clubhouse Heated pool 2 tennis courts Pickleball Manicured grounds with walking paths Whether you're looking for a full-season rental or a month-by-month stay, this home delivers carefree luxury with every convenience just minutes from East Hampton Village and world-class beaches and restaurants. Sorry, no pets. HOA: Georgica Estates. Rental Terms: Two Weeks: $18,000 August - Labor Day: $45,000 August: $38,000

Spectacular living awaits in Sagaponack South, this bespoke home offers 10,000 +/- square feet on 1.5 +/- private acres. Custom build in 2013, this chic residence features seven spacious bedrooms and seven+ baths. This modern masterpiece was designed by Francis D'haene of the award winning architectural firm D'apostrophe Design. Enter into breathtaking light-filled living space graced by walls of glass through a dramatic double-height entryway with a travertine floating staircase and solid white oak floors. This home includes an 68' heated gunite infinity pool, pool house, outdoor shower and full outdoor dining/kitchen area. The ultimate setting for entertaining and enjoyment. 183 Daniels Lane makes a grand statement of elegance while affording contemporary comfort. Rental Terms: Two Weeks: $200,000 August: $450,000 Memorial Day - Labor Day: $950,000 August - Labor Day: $500,000 July: $400,000 June: $200,000

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: July - Labor Day: $300,000 August - Labor Day: $175,000 July: $150,000 Other / Short Term - 10/1/2026 - 4/30/2027: $55,000 June: $75,000

A simple Sagaponack ocean beach vacation home. Three bedrooms, 2 bathrooms, central air conditioning, indoor & outdoor dining. .3 miles to Town Line Beach. Perfect for an easy, low maintenance, low expense beach focused summer vacation. Rental Terms: Memorial Day - Labor Day: $50,000 August - Labor Day: $22,000 June: $14,000 July: $18,000

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

Modern beach cottage on three acres with beautiful ocean views and pathway to the beach. 3 bedrooms, 2.5 baths and expansive decks, from which to enjoy the ocean breezes. Available May 27th - Jul 19th 2021- $55,000 August-LD: Jul 30th - Sep 6th 2021- $55,000 Rental Terms: August - Labor Day: $55,000 Other / Short Term - June/July: $55,000

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: 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: October: $25,000 Other / Short Term - Year Round: $220,000

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

Set South of the Highway in East Hampton, this pristine traditional offers an idyllic Hamptons retreat just moments from Main Beach and East Hampton Village. Beautifully maintained throughout, the home features four generously sized bedrooms, an inviting open living room with fireplace and built-in library, and an eat-in kitchen that flows seamlessly into a cozy sitting area. A formal dining area with sliding glass doors creates an effortless connection to the outdoors and an ideal setting for entertaining. Just off the primary suite, a private study offers flexibility as a home office or fifth bedroom. Set on 1.2 acres of lush, rolling lawn framed by mature specimen trees, the property offers exceptional privacy and a peaceful setting in one of East Hampton's most desirable locations. Rental Terms: July: $40,000 Memorial Day - Labor Day: $125,000 July - Labor Day: $85,000 June/July: $50,000 August - Labor Day: $50,000

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: July: $55,000 February: $8,000 January: $8,000 Memorial Day - Labor Day: $160,000 November: $8,000 March: $8,000 August - Labor Day: $75,000 Other / Short Term - Dec: $8,000 October: $8,000 April: $10,000 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

Bright and open home offers an inviting living space complimented by vaulted ceilings over sized windows and sliding glass doors. A perfect environment for socializing and gathering. The home is designer decorated with a mix of contemporary and country farmhouse beachy furnishings. Muted greys & blues are found throughout the home. The centrally air conditioned home features an open concept with the kitchen opening up to the living room and dining area. Professional appliances and every imaginable kitchen gadget needed for a gourmet chef. The Carrera marble island is a perfect gathering spot for morning coffee. There is a farm table with seating for 8. Each of the bedrooms has comfy beds with brand new linens including comforters with 100% high thread count cotton duvet covers. The home is supplied with bath towels and separate pool towels. There is a lower level media room for watching your favorite movie and huge indoor recreation area that includes a hockey/soccer rink and some toys. Step out of the sliding backdoors onto a deck which overlooks the pool. The backyard of the home looks onto a private 50 acre reserve where you will find running and hiking trails. The deck is well equipped with dining areas, seating, lounge chairs and gas BBQ. Additional accessories will include beach chairs, umbrellas and coolers for beach. 3 bedrooms , 3 bathrooms Finished Basement with TV room/Playroom/Hockey Soccer Rink Open kitchen/living/dining space with vaulted ceilings Bright open sunny home Fully equipped gourmet kitchen Central A/C Heated Natural Salt Water Pool Located on quiet cul de sac in private community 4 miles to Ocean Beach 2 miles to downtown Bridgehampton 3 miles to downtown Sag Harbor Keyless Entry System Private VIP Concierge Services Available during Summer Season Bedroom One: King Bed with ensuite bathroom Bedroom Two: Queen Bed with shared bathroom Bedroom Three: Two sets of bunkbeds, four twin beds with shared bathroom. [[Rental Registration # RP230214]] EH RR #: RP230214 Rental Terms: June: $25,000 Memorial Day - Labor Day: $110,000 July: $45,000 August - Labor Day: $55,000

Charming, well-maintained home located in the heart of Bridgehampton. The main house offers 3 bedrooms (including 1st floor primary w/en-suite bath), 2.5 beautifully updated baths (2024), living room, kitchen, den/study, screened porch, separate office and garage. The manicured lawn and mature plantings provide an exceptionally serene setting, while the the in-town location is just minutes to Main Street and the glorious ocean beaches of Bridgehampton. Pets considered on case by case basis. [[Rental Registration # RA240652]] EH RR #: RA240652 Rental Terms: Other / Short Term - Dec: $4,500 January: $4,500 February: $4,500 March: $4,500 November: $4,500 May: $13,000 June: $17,000 April: $4,500 October: $10,000