luxury houses with terrace for rent Bridgehampton, United States

Discover the perfect Fall getaway in this stunning artist's home in Sag Harbor, now available from Sept 8th - Oct 5th 2026. Ideally situated between Sag Harbor Village and Long Beach, this immaculate 4-bedroom, 3.5-bathroom residence is a true oasis, featuring a well-curated collection of art within a sophisticated monochromatic interior. Built in 2018, this contemporary farmhouse beautifully balances exceptional style and comfort. An open-plan kitchen, dining, and living area seamlessly transitions to the 32' x 16' heated gunite pool, surrounded by a bluestone patio with multiple entertaining and lounging areas. A well-thought-out setting for summer gatherings or long days by the poolside. For the art enthusiast, a well-stocked library of art and design books can be found in the first-floor lounge. On the second floor, you will find four well-appointed bedrooms, including two that feature ensuite bathrooms, as well as an additional full bathroom. To enhance your stay, the dedicated laundry room features two washers and dryers for your convenience after days at the beach. Minutes from both Long Beach and Sag Harbor Village, you can also enjoy fresh, local produce from Serene Green Farm Stand, conveniently located at the end of Parkway Drive. [[Rental Registration # RP230356]] EH RR #: RP230356 Rental Terms: October: $18,000 July: $60,000 July - Labor Day: $135,000 Other / Short Term - 12/23/2026 - 1/31/2027: $30,000 September: $12,000 August - Labor Day: $75,000

Step into the season with a top-to-bottom Spring refresh-brand new mattresses, crisp bedding and towels, a sparkling new kitchen stove, a sizzling barbecue, and a fresh coat of paint. Watch the sunsets dance across the water and feel the cool breezes that make every evening unforgettable. With a sandy entrance to Sag Harbor Cove for a refreshing dip and an outdoor shower to rinse off, it's the perfect blend of charm and modern comfort. This gem is priced right and ready for your best summer yet-just unpack and start making memories! [[Rental Registration # RA240090]] EH RR #: RA240090 Rental Terms: September: $10,000

Welcome to 54 Bay View Drive East, Sag Harbor, where modern luxury meets waterfront living. This stunning, award-winning modern estate is a boater's paradise, boasting a deep water dock and breathtaking sunset views over Sag Harbor Cove. With 4 bedrooms, 4.5 modern baths, and 3100 square feet of sleek living space, this home offers the epitome of waterfront elegance. A primary suite on the first floor and an additional secondary primary bedroom suite on the second floor with endless water views complement this unique offering. Enjoy the convenience of a water view Chef's kitchen, multi-level decks, and a heated Gunite infinity pool. The property features geothermal heating and cooling, ensuring comfort with minimal environmental impact. Custom fixtures from Italy and an outdoor wood-burning pizza oven add distinctive charm. Located near Sag Harbor's amenities, a 10 min walk to Long Beach, and the Shelter Island Ferry, this home offers a unique summer retreat. Don't miss the opportunity to experience waterfront luxury at its finest. [[Rental Registration # 251021]] EH RR #: 251021 Rental Terms: August: $185,000 August - Labor Day: $225,000

Situated on one of the largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club.ond largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club. Rental Terms: May: $20,000 September: $38,000

New Kitchen Renovation!! Modern waterfront residence with expansive yard and private dock near Long Beach. Enjoy long summer days sailing, kayaking, swimming or swinging in the yard and followed by family bbqs. Great location with proximity to Sag Harbor village restaurants and shops and private outdoor oasis. Revel in spectacular sunset views from the wrap around deck with comfortable seating that is also perfect for outdoor dining and entertaining. Rental Reg. # RP201766 - Reg. Expires 6/07/2023 EH RR #: RP201766 Rental Terms: Other / Short Term - Year Round: $375,000

Great home for entertaining. Very attractive contemporary in country setting. Five bedroom, four bath home in Water Mill with heated gunite pool plus entertainment room in lower lever. [[Rental Registration # RP201246]] EH RR #: RP250236 Rental Terms: June: $35,000 August - Labor Day: $70,000 July: $60,000 July - Labor Day: $125,000 Memorial Day - Labor Day: $150,000 September: $30,000

Newly renovated in 2018, this bright and airy four-bedroom home is set on a full acre bordering a private preserve, offering rare tranquility and uninterrupted natural views in the heart of Water Mill. The home is filled with natural light throughout, featuring an open-concept kitchen and living space designed for easy summer living and seamless entertaining. The primary suite opens directly to the outdoor deck, creating a true indoor-outdoor lifestyle. Outside, enjoy expansive, fully fenced grounds, a sparkling in-ground pool, and the privacy that comes with backing onto preserved land. Privacy with just sun, space, and calm. Ideally located minutes from ocean beaches, Southampton, and Bridgehampton villages, and top restaurants, this home delivers both convenience and escape. A clean, modern Hamptons rental that actually feels like a getaway. Available August through Labor Day. [[Rental Registration # RP260066]] EH RR #: RP260066 Rental Terms: Other / Short Term - Year Round: $125,000 Memorial Day - Labor Day: $85,000

Welcome to 4 Scrimshaw Drive, located in the sought-after Whalebone Landing community, where summer feels calm, private, and effortlessly beautiful. Enjoy the private bay beach and tennis courts just moments away, and quick access to the boutiques, restaurants, and harbors of both Southampton and Sag Harbor. Designed for luxury summer living, this home features a heated gunite pool, sun-filled interiors, and three levels of finished living space ideal for both relaxation and entertaining. Coastal-inspired details throughout the home create a natural sense of ease and timeless Hamptons elegance. With convenient proximity to the U.S. Open PGA at Shinnecock Hills Golf Club in June 2026, this residence offers a refined retreat for those seeking to experience the very best of the Hamptons with style, privacy, and comfort.

This light-filled residence is quietly set on a gated and exceptionally private two-acre property in coveted Water Mill. Recently renovated with a natural, timeless aesthetic, the home features sanded oak floors and a thoughtful layout with five beautifully appointed bedrooms across two distinct wings. A welcoming foyer opens to a spacious living and dining area, highlighted by a wall of sliding glass doors that seamlessly connect to the deck and outdoor living spaces. First-floor guest suite enjoys direct access to the deck and pool. Upstairs, the primary suite and an additional guest ensuite share a balcony, alongside a dedicated workspace ideal for focused productivity. A separate wing offers a media / playroom and two additional bedrooms, including one with bunks, served by a full bath-perfect for guests of all ages. Outdoors, enjoy a heated pool and relaxed al fresco dining surrounded by mature landscaping, hydrangeas and natural tranquility. Ideally located just eight minutes from Southampton Village's renowned restaurants, shops, and ocean beaches, this serene and special property offers privacy, comfort, and effortless Hamptons living. Please call with questions or to make an appointment to view this serene and special property! [[Rental Registration # RA260488]] EH RR #: RA260488 Rental Terms: August - Labor Day: $65,000 August: $55,000

Perfectly positioned in the heart of Bridgehampton South, this beautifully designed six-bedroom, five-and-a-half-bathroom home embodies effortless Hamptons living in every season. Filled with natural light, the home offers elegant, sun-drenched interiors, sophisticated yet relaxed furnishings, and a seamless flow between indoor and outdoor spaces. Thoughtfully designed for both comfort and style, expansive living and dining areas create the perfect setting for everyday living, entertaining, and weekends with family and friends. Beautifully landscaped grounds offer multiple outdoor seating and dining areas, while a tucked-away fire pit provides an inviting place to gather on crisp fall evenings or cool spring nights. Designed with every member of the family in mind, the property also features a basketball court, trampoline, playground, and garage, offering plenty of space for recreation and relaxation throughout the year. Located moments from Bridgehampton's renowned restaurants, boutiques, farm stands, ocean beaches, and equestrian facilities, the home offers an ideal balance of privacy, comfort, and convenience - from quiet fall weekends and cozy winters to spring on the East End and the arrival of summer. An exceptional opportunity to experience Bridgehampton living through the seasons. [[Rental Registration # Pending]] Rental Terms: Other / Short Term - 9/12/2026 - 6/30/2027: $195,000 February: $15,000 May: $40,000 October: $35,000 November: $20,000 September: $60,000 January: $15,000 April: $20,000 March: $15,000 June: $75,000

This very high-end, newer construction home is available for rent from July 1-Aug 15th, for 2-3 weeks or 1 month. Gorgeous architecture, landscaping and stylish designer interiors are hallmarks of this classic estate. The private gated home sits on a full-lawn property on a quiet street, buffered by fields in front and a pretty tree farm in back. The inside features high-end, custom-designed furnishings and art curated by Mabley Handler, one of the Hamptons most sought-after designers. The nearly 9000SF home offers the ultimate backyard--with an oversized pool with overflowing Hot Tub, and thousands of feet of patios and terraces. You have your choice of entertainment areas, including covered porches, pergolas, open terraces, a fireplace area and a pool house area. Nestled in the heart of Water Mill's horse country on a quiet cul-de-sac, this sleek shingle-style transitional home offers the finest in Hampton's living. Beyond the private gated entrance, the 6 Bedroom home (all with ensuite baths) spans 6300 feet above ground, with a 2500 SF, gorgeously finished lower level. The home features a dramatic 2-story paneled foyer that opens to three different living rooms--a great room, living room and TV room. The kitchen is enormous, designed by Bakes & Kropp kitchen, with a large breakfast area overlooking the yard and a butler's pantry that leads to the formal dining room. The second floor features an enormous primary suite with adjoining sitting room/office and a terrace with views. There are 4 additional ensuite designer bedrooms upstairs. The lower level is truly gorgeous and an extension of teh upstairs. If offers an expansive windowed entertainment space, including a living room, new theater, and an additional bedroom with ensuite bath. There is a state-of-the-art gym, spa bath, sauna and steam room. Spend each day relaxing on the expansive, south-facing terrace with all day sun. The pool house--with kitchenette, living room, outdoor shower and laundry--offer every amenity at your fingertips. The house is controlled by a fully integrated Control 4 Smart system. [[Rental Registration # Pending]] Rental Terms: Two Weeks: $95,000 June: $125,000

Be the first to experience this brand new modern twist to a classic Hamptons home. This high-end construction flawlessly combines modern and sophisticated interior finishes with a classic exterior design. This beautiful 6 bedroom, 8 bathroom home situated on 1.6 =/-acres, features a sunken Tennis court, oversized Gunite Pool and Pool House. All within minutes of stunning Southampton beaches and Southampton, Watermill and Sag Harbor world-class dining making this the perfect Hamptons getaway. Experience elegant European living with cathedral-style ceilings and an open layout throughout the ground level, while the hidden pocket doors still make each room feel private. Each of the living spaces has direct access to the bluestone terrace with a pergola and retractable awning. The first floor also has a primary bedroom suite, den, formal dining room, and large eat-in kitchen. The expansive living room can be admired from the second-floor gallery. The four bedrooms on the second floor are all en-suite with walk-in closets. The lower level has an additional two bedrooms, gym/spa, home theater, wine cellar, Laundry, and ample natural light with a generous walk-out lounge area. [[Rental Registration # RP230526]] EH RR #: RP230526 Rental Terms: July: $190,000 June: $200,000 September: $150,000

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

Experience the epitome of coastal living just steps from the serene shores of Towd Point Beach. Featuring newly refinished white oak flooring, farmhouse kitchen, Central A/C, BBQ slate patio & deck, hammock, outdoor shower, large lawn and bloom filled gardens. And of course easy access to the beautiful Towd Point beach for swimming and stunning sunsets. Kayaks included and Pet Friendly too! [[Rental Registration # RP260737]] EH RR #: RP260737 Rental Terms: May: $8,000 Two Weeks: $8,000 June: $12,000 August: $19,000 July: $17,000

360-degress water views from every room at this delightful beach house perched on Flying Point with direct "put-in" access to Mecox Bay. This house offers an ideal open floor plan with powder room on the first floor and on the second floor, the primary en suite, two guest bedrooms and the second full bathroom. Easy, breezy, beachy living in a prime location. Amenities include a fully-modern kitchen with stainless appliances, water-facing decks on two levels with views to Channel Pond and the ocean, an outdoor shower, and its own private walkway to Mecox Bay. Only one property separates this house from ocean beach access at Flying Point, and the private walkway makes kayaking and paddle boarding easy. Very bright and beautifully furnished. Available for August and/or September as well as many other months in extended season. [[Rental Registration # RP260252]] EH RR #: RP260252 Rental Terms: September: $35,000 November: $12,000 Other / Short Term - Year Round: $220,000 August: $72,500 August - Labor Day: $75,000 October: $18,000

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate guests. Angel Shores is known for its sandy Peconic Bay beach, just a short stroll down the road, perfect for easy beach days and watching sunsets by the water. The home is also conveniently close to Southold’s wineries, farm stands, and village amenities, putting the best of the North Fork right at your fingertips. 2026 Availability: June 16-June 30th $7,000, July $23,000, August $25,000 August-Labor Day $27,500. Permit # 0956

Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect for entertaining. Additional conveniences include an in-unit laundry room, mudroom, and a flexible bonus space great for a home office or playroom. A two-car garage provides ample storage and parking options. Located just minutes from Route 114 and South Ferry, the home offers easy access to all the island’s main destinations. Wades Beach is only 1.5 miles away, making beach days effortless. Guests also enjoy seasonal access (July 4th–Labor Day) to the Coecles Harbor Marina pool for added summer enjoyment. This peaceful retreat combines comfort, privacy, and convenience—ideal for your next stay on Shelter Island.

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

This handsome residence is situated on a well-landscaped acre. A bright living room with fireplace and double-height ceiling, dining area, eat-in kitchen, four bedrooms with primary on first floor and three baths provide good living space. Central air-conditioning, two-car garage, outdoor deck, and heated pool complement this home. Located minutes from the Village of Southampton, this property is close to all beaches, shopping and restaurants. [[Rental Registration # RP240739]] EH RR #: RP240739 Rental Terms: June: $18,000 July: $30,000 August - Labor Day: $35,000 September: $15,000 Memorial Day - Labor Day: $65,000 July - Labor Day: $60,000

Convenience at its best. Newly constructed and first time available for rent. This pristine traditional home is located in the heart of Southampton village. The main floor has an open layout with lots of natural light. Gourmet kitchen, living room with fireplace, wet bar and dining area. There is a first floor en-suite bedroom. Second level has 2 guest bedrooms with a shared bath, master suite and laundry room. Lower level has a sitting area, bedroom and bathroom. There is a heated gunite pool, out door fireplace, outdoor pool bath and detached one car garage. Rental Terms: August - Labor Day: $135,000 July: $120,000 Memorial Day - Labor Day: $245,000 July - Labor Day: $230,000

This picturesque traditional on East Hampton Village's Osborne Lane is now available for two weeks at summer's end. Just doors away from Newtown Lane and the heart of village attractions, this lovely home offers a wonderful combination of summer charm and local convenience. Highlights of the first floor include a large entry foyer, a double-height living room with wood burning fireplace, a spacious chef's kitchen with high-end appliances and center island, a stylish dining room, a separate den, a screened-in porch, a half bath, and the primary bedroom with a gas fireplace, two walk-in closets, and an en suite marble bath. The second floor includes three large guest rooms, each with its own en suite bath. The lower level has been finished and offers another living space with TV, wet bar, and wine refrigerator, a gym outfitted with Peleton, Pilates, and free weight equipment, a bonus room, and additional full bath. The backyard is highlighted by a large gunite pool surrounded by bluestone, an expansive lawn, tall evergreens providing ample privacy, a hot tub, and extra decking and patio space - both ideal for entertaining. This exceptional property affords a wonderful sense of warmth and enjoyment while remaining close to world-class restaurants, shops, transportation, and beautiful ocean beaches. [[Rental Registration # 24-941]] EH RR #: 24-941 Rental Terms: Two Weeks: $75,000

A stone's throw from the heart of East Hampton Village, this fully renovated and thoughtfully designed home offers the perfect Hamptons escape. Privately set behind mature landscaping and a gated entry, this new rental delivers a rare combination of charm, convenience, and turnkey ease. Inside features two well-proportioned bedrooms and two full baths, complemented by a spacious living room and eat-in kitchen. Outdoors, enjoy a private yard ideal for relaxing or entertaining after a day at the beach. Minutes to village shops, dining, and the area's most desirable ocean beaches. [[Rental Registration # RR-26-353]] EH RR #: RR-26-353 Rental Terms: July: $16,000 Winter Season: $21,000 Per Month Other / Short Term - Year Round: $75,000 August - Labor Day: $28,000 Memorial Day - Labor Day: $45,000 July - Labor Day: $38,000 June/July: $25,000

Enjoy this tastefully decorated, eight-bedroom, eight-bath Traditional home just around the corner from Gin Lane and the ocean. A wonderful opportunity to spend a summer in a perfect European-styled home in the Southampton Estate Section. The house has an open floor plan on the first floor offering a the state-of-the-art kitchen, breakfast area, formal dinning, wet bar and a downstairs bedroom. The six, wonderfully furnished, additional upstairs bedrooms, each with a bathroom and some with private terraces, are accessable through two different staircases. The basement is setup with a staff area and a brand new, huge media room. There is plenty of outdoor entertaining terraces with fireplace, a beautiful pool and nicely landscaped gardens. Rental Terms: July: $160,000 June: $80,000 Winter Season: $100,000 Per Month September: $50,000