luxury houses with pool for rent Bridgehampton, United States

Down a long drive, this charming Hamptons classic house is situated on a professionally landscaped acre. Tucked away in a quiet community and only a stone's throw to both Bridgehampton and Sag Harbor villages. This stylish professionally decorated home is fully equipped with 4 bedrooms and 2.5 bathrooms. The first floor boasts a sun-drenched great room with designer furniture and lighting, wide plank floors and a brick fireplace. Additionally, there is a master bedroom with an en suite bathroom. The kitchen is beautifully appointed with a top of the line Lacanche oven, there is also a powder-room, large pantry, laundry and mudroom with access to the pool and back garden. The second floor has three additional guest bedrooms with beautiful views of the grounds, one of the bedrooms has a walk-in closet and on the second floor there is an oversized shared bathroom. Ideal for summer entertaining the back and front gardens offers complete privacy with an expansive wrap around deck, a heated pool, outdoor shower, and a generous fenced in yard. A true gem not to be missed! #RP201221 Exp 2/10/2025 [[Rental Registration # RP250191]] EH RR #: RP250191 Rental Terms: Two Weeks: $20,000 July: $40,000 July - Labor Day: $85,000 August - Labor Day: $50,000

Tucked away down a long, private driveway is this spectacular cottage in Bridgehampton South. Conveniently located just behind the village, this one-story home has been recently renovated and refreshed with crisp new furniture. A cozy front porch and stunning cherry blossom tree welcome you, while interior highlights include an open concept living and dining room highlighted with a wood-burning fireplace and lovely reading nook illuminated with Venetian lanterns. A new backsplash adorns the separate kitchen that opens via a pass-way into the dining area. The primary bedroom has sliding glass doors and a newly renovated en-suite bath with beautiful tile and separate shower. Two additional guest rooms and another renovated bathroom complete the interior space of this finely decorated home. The backyard is tastefully landscaped and adorned with bamboo and tall specimen trees, including a spectacular weeping willow, to help ensure privacy. A large heated pool is flanked by a sunny patio and added decking for great entertaining, all with easy proximity to Bridgehampton shops, restaurants, transportation and ocean beaches. [[Rental Registration # RP220699]] EH RR #: RP261324 Rental Terms: July: $45,000 August - Labor Day: $55,000

Set on 1.2 acres with distant ocean views, this 5 bedroom home was renovated in early 2014 to provide a new kitchen, 7.5 new bathrooms, and a finished basement with a gym and recreation room. The house features high ceilings with light filled rooms. Privacy abounds since the master bedroom and the ensuite bedrooms are located in three distinct areas of the house. The first floor offers an eat-in kitchen, spacious living room and dining area, comfortable family room, and one of the ensuite bedrooms. A separate study with its own private full bath can serve as a 5th bedroom. Outside, ample decking and tables overlook the 54' heated gunite pool and spa. Mature, lush landscaping and an outdoor shower complete the picture. Also available June 2023 for $30K. EH RR #: RP260632 Rental Terms: July: $100,000 August - Labor Day: $125,000 July - Labor Day: $200,000 June/July: $150,000 Memorial Day - Labor Day: $250,000

Get ready for the perfect summer vacation in this newly renovated and fashionably furnished Bridgehampton Estate. Entering into an oversized living room, this home has many gracious living spaces. The first floor has a newly designed master suite, walk-in closet, oversized master bath, with a gracious shower, soaking tub, and a private covered porch, with heat lamps. There are three additional bedrooms that are all beautifully decorated with newly renovated baths. The kitchen is sun-filled with sleek cabinetry, and a built-in stone dining table. The lower level is fully finished and is great for lounging and watching movies, or the perfect place for the little ones to play. The backyard has it all. Enjoy your summer days lounging around the heated pool and grilling on the beautiful deck enjoying spectacular western sunsets. The backyard is very private with tall hedges, beautifully manicured landscaping, and agricultural reserve views. Located on Lumber Lane, this home has the perfect location. You are minutes to Bridgehampton town and a straight shoot to the beach, driving up Ocean Road. You are also super close to Sag Harbor Village, perfect for dinners out with the family, or casual shopping. [[Rental Registration # Pending]] EH RR #: ra241558 Rental Terms: July: $110,000 July - Labor Day: $230,000 August - Labor Day: $125,000 August: $110,000

Immaculate traditional in Bridgehampton North. 5 bedrooms, 3.5 baths on just under 2 acres of beautifully landscaped property. Large mahogany deck with outdoor BBQ and heat lamps. Oversized heated saltwater gunite pool overlooking western sunsets. A wonderful Hamptons retreat. [[Rental Registration # RP200229]] EH RR #: RP200229 Rental Terms: June: $40,000 August - Labor Day: $70,000 July: $65,000

Also available: June for $35K; June/July for $125K Enjoy the beauty of this recently renovated five bedroom, five-and-a-half bath traditional in Bridgehampton's horse country. This 4,500+/- square foot home sits on a beautifully manicured full acre with open lawns and a 20' x 40' gunite pool. A large double-height foyer and beautiful staircase greet you as you enter the home while a chef's kitchen and spacious, nicely appointed primary suites on both levels are just some of the other amenities featured in this summer oasis. Close proximity to town, shops, restaurants and beaches complete this spectacular property. Reach out now to secure this wonderful home for summer 2023. Rental Reg #: RP230579 EH RR #: (RP251002) Rental Terms: June: $50,000

57 Jobs Lane, a magical very special 2 house property on 2 park like acres mere moments from the Ocean and Bridgehampton town. The property offers charming parlors, 4 guest rooms, 2 baths, and primary suite complete with a private deck and sitting area within the main house. The open kitchen seamlessly connects to a grand living room, while a dining room leading to alfresco outdoor dining, oversized 75ft pool and the most enchanting guest house with ensuite bedroom, living room, a well-appointed kitchen and its own private outdoor patio. [[Rental Registration # RP260545,RP260546]] EH RR #: RP260545, RP260546 Rental Terms: September: $75,000 Memorial Day - Labor Day: $250,000 August - Labor Day: $150,000 July: $90,000 June: $35,000

Ideally situated South of the Highway in Bridgehampton, this exceptional rental offers the quintessential Hamptons lifestyle on a beautifully cleared, one-acre parcel. Tucked away on a quiet cul-de-sac, the property offers a rare combination of privacy, tranquility, and convenience, just moments from ocean beaches, horse farms, world-class dining, shopping, and everything the Hamptons has to offer. The light-filled residence is designed for effortless summer living and year-round enjoyment, with generous spaces for relaxing and entertaining. A welcoming living room with fireplace, updated kitchen and dining area, which flows seamlessly to a grand oversized screened-in porch. The first floor also features a comfortable junior primary bedroom, and a dedicated home office area overlooking the pool. Upstairs, the gracious, private primary suite is joined by two additional guest bedrooms, providing comfortable accommodations for family and guests. Outside, a heated gunite pool with fencing takes center stage amid mature landscaping and expansive, fully cleared grounds. There is abundant room to lounge poolside, dine al fresco, entertain, or simply enjoy the serenity of the property. Additional amenities include a two-car garage and generous parking. With its coveted South-of-the-Highway location, peaceful setting, spacious interiors, resort-style pool, and proximity to the ocean, this is a distinctive opportunity to experience Bridgehampton at its best. Available as a summer or year-round rental. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: Other / Short Term - Year Round: $250,000 June: $35,000 August - Labor Day: $75,000 Memorial Day - Labor Day: $175,000 July: $65,000

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: July: $350,000 June/July: $500,000 Other / Short Term - Year Round: $1,300,000 July - Labor Day: $700,000 August - Labor Day: $400,000 June: $200,000

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

In a prime Bridgehampton North location just minutes from ocean beaches, Bridgehampton Main Street, and Sag Harbor Village, this recently refreshed shingled traditional offers bright, effortless, and stylish summer living. Light updates and new décor give the home a fresh, current feel throughout. The sun-filled living room, with its vaulted, beamed ceiling and fireplace, creates an inviting centerpiece that flows into the country kitchen and cheerful dining area. A classic screened-in porch provides a perfect spot for breezy mornings or relaxed evenings by the pool. The first-floor primary suite is a standout, featuring a vaulted ceiling, beautiful natural light, and an easy, elevated atmosphere. A versatile den that can serve as a fourth bedroom offers added flexibility, while two upstairs bedrooms share a full bath. Light pine floors, abundant sunlight, a generous landscaped acre, ample parking, and a sunny pool area all contribute to the home's relaxed Hamptons appeal. Thoughtful accessibility features-including a first-floor bathroom designed for ease of use and a discreet wheelchair ramp at the front of the home-add convenience without interrupting the home's classic aesthetic. This inviting Bridgehampton retreat blends style, comfort, and practicality, making it an ideal rental for a cheerful and easy summer. [[Rental Registration # (RP251526]] EH RR #: (RP251526 Rental Terms: Two Weeks: $20,000

This bright and spacious home, nestled down a private driveway and adjacent to a scenic reserve, is a hidden gem off Lumber Lane in Bridgehampton. Ideally located between the charming Villages of Bridgehampton and Sag Harbor, and a short distance from both ocean and bay beaches, this delightful 3-bedroom house boasts a second-floor primary bedroom with its own deck. The expansive double-height living room flows seamlessly to the dining area and a well-appointed chef's kitchen. Glass doors open to a generously sized deck, perfect for summer gatherings, overlooking the inviting heated pool. A detached garage, featuring a home office, adds to the appeal. Residents may also enjoy access to nearby tennis courts, enhancing the quintessential Hamptons experience [[Rental Registration # RP201993]] EH RR #: RP252090 Rental Terms: Memorial Day - Labor Day: $95,000 July - Labor Day: $80,000 June: $20,000 August - Labor Day: $42,000 July: $38,000

Experience the ultimate Hamptons summer at this spectacular 7-bedroom luxury estate in the heart of Bridgehampton, surrounded by premier horse country, vineyards, farm stands, and just minutes to world-class beaches, village dining, and shopping. Recently constructed and impeccably furnished, the interiors were custom-designed by acclaimed designer Alicia Murphy, blending elevated coastal sophistication with relaxed summer living. A charming gated courtyard and welcoming front porch set the tone on arrival, while a dramatic double-height entry leads into a sun-filled great room ideal for entertaining or unwinding. Throughout the home, exquisite stonework, bespoke millwork, and designer finishes reflect meticulous craftsmanship-no detail overlooked from architectural plans to final installation. The open flow layout connects beautifully to the outdoors, creating seamless indoor-outdoor living. The property features: 7 Bedrooms & 6 Baths across three finished levels 20x40 heated gunite pool with stone patio Expansive private grounds & lush professional landscaping Al fresco dining & multiple outdoor lounge areas Finished lower level with bedroom suite, family/TV room, wet bar & gym Attached 2-car garage and ample parking This is a rare Bridgehampton summer rental, offering luxury, convenience, and privacy-the perfect Hamptons retreat close to ocean beaches, Bridgehampton Village, Sag Harbor, acclaimed restaurants, equestrian facilities, wineries, and golf. Available in June for two weeks or the full month of August for the discerning tenant seeking the ideal Hamptons summer experience. Rental Terms: August: $175,000 August - Labor Day: $195,000 July - Labor Day: $350,000 Memorial Day - Labor Day: $450,000 June: $100,000 July: $175,000

This five bedroom, 6.5 bath home, located on a private cul-de-sac street approximately 1 mile from the ocean, is perfectly sited on a beautifully landscaped acre. The front door opens onto a large, bright foyer. To the left is the living room with fireplace, baby grand piano, and 2 sets of doors leading to the covered porch facing south and the deck facing west. To the right of the foyer are the formal dining room and elegant powder room. Overlooking the rear yard is the fully equipped, renovated eat-in kitchen with stainless steel appliances including a Sub-Zero refrigerator, gas range, 2 dishwashers, and wine cooler. Down a short hallway are the family room with a fireplace and high ceilings and a room serving as the pool cabana, featuring a refrigerator, washer/dryer, and full bath. The main staircase in the foyer leads upstairs to the primary bedroom suite with a king-size bed, walk-in closet, and luxurious bathroom; an en-suite bedroom with a king-size bed; 2 additional bedrooms, each with a queen-size bed, which share a hallway bath; and a second laundry with washer/dryer. The 2nd staircase by the family room leads to a private 2nd floor en-suite bedroom with a king-size bed and to a separate office. The lower level has a finished recreation room and a full bath. Outside, there are multiple seating areas: the south-facing covered porch; the deck facing west with a Weber grill and large teak dining table for 12; and a patio surrounding the gunite pool with a variety of wicker furniture and comfortable lounge chairs. The grounds are lushly landscaped with spectacular gardens and ample grassy areas. Adjacent to an agricultural reserve, the property offers spectacular sunset views. [[Rental Registration # RP241855]] EH RR #: RP241855 Rental Terms: July: $89,500

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

Dramatic Contemporary in a beautiful location, with wide Mecox bay views to the north and the sandy ocean beach to the south. This top notch, well equipped and maintained contemporary features a huge living room accessing ocean or bay decks, a formal dining area, a media room, a gourmet's eat in kitchen, a private master suite with a deluxe bath featuring a shower with ocean views and an office, a full gym, 6 additional bedrooms and 9 additional baths, a heated pool and spa surrounded by spacious decking and overlooking the ocean completes this special home. [[Rental Registration # RP190323]] Also, available for annual rental, price upon request. EH RR #: RP250632 Rental Terms: July: $495,000 Memorial Day - Labor Day: $1,300,000 Two Weeks: $350,000 August - Labor Day: $595,000