51 houses for rent in Wainscott

Summer discount you can’t miss on this one! Also available for mid July-Labor Day for $300,000 For other dates, please inquire Beyond a discreet approach on one of East Hampton Village's most coveted waterfront lanes, 64 West End Road unfolds as a rare and irreplaceable estate where land, water, and privacy exist in perfect harmony. Set on 2.71± acres with an extraordinary 970± feet of direct frontage along Georgica Pond, this remarkable property commands one of the most breathtaking settings in the Hamptons, offering uninterrupted views that stretch from the tranquil waters of the pond to the Atlantic Ocean beyond. Positioned at the end of its own private cove and surrounded by protected land, the estate enjoys a level of privacy that is nearly impossible to replicate. From sunrise reflecting across the pond to the legendary sunsets that paint the western sky each evening, every moment here is framed by water, light, and nature. Few properties in East Hampton Village offer such an imm

This is not a home, it’s a LIFESTYLE RESORT, a HOUSTEL called WILLIEVILLE. If you enjoy entertaining, then this home is for you. Everything you can imagine is perfectly set up—no detail has been overlooked, including THE FORCYNTHIA VINEYARD EXPERIENCE, where a full case of private reserve Rosé is included each week. This 8 bedroom, 9.5-bath, industrial modern barn built and designed by celebrity lifestyle restaurateur William Jack Degel, is located on 1.83 acres in Watermill's pristine horse country. The outdoor oasis features a 2,000 square feet covered outdoor living space with a full kitchen, fridge, pantry, bar, lounge, fireplace, dining area, 85 inch TVs, infrared heaters, and a covered raised 12 person heated spa. The private vineyard in the back drop named FORCYNTHIA, showcases Wolffer grapes and picnic tables. Adjacent is the 50-foot gunite saltwater pool, 10 by 10 raised spa, a sunken all-weather pickleball, basketball sports court, 700 hedges, 1,200 seasonal flowering perenn

This perfectly located Sag Harbor Village waterfront home with a private dock is ready for your enjoyment! Situated on the storied and private Bluff Point Lane, this home offers unmatched tranquility and generous views of Upper Sag Harbor Cove! This special home boasts three bedrooms, one and a half baths, an inviting living room with a fireplace, dining table overlooking the water, ample decking to enjoy spectacular sunrises and sunsets, outdoor shower and so much more! This is a must see! Available 10/1/2026 - 4/30/2027 $6k/month

Available for 2026 US Open for $100,000 This incredible modern-traditional 7 Bedroom, 7.5 Bath home features 8457+/- sqft of living space including extensive ground level and 1st floor deck. Completed in 2021, the new construction is situated on a very private 2.80 +/- acres in beautiful and convenient Water Mill. A covered front porch provides access to a grand double height foyer with great room and upper deck. The formal dining room in the front of the building connects the large gourmet chef's kitchen with breakfast room and butlers pantry with wine fridge. The great room and separate living room share a beautiful double exposure fireplace and a huge junior primary bedroom with walk-in closet features a private bath with double sinks. Upstairs, an impressive master suite has a grand bath with soaking tub, two walk-in closets and a separate linen closet. Three additional guest bedrooms each with en-suite baths are also located on this level with a convenient double capacity laundry

Enjoy this newly renovated Southampton Village home with 5 bedrooms and 7.5 baths which boasts 5,300 sq. ft. and features all new high-end staged furnishings and accessories that encompasses everything needed to enjoy a spectacular summer. Included in this full open concept design are beautiful wide plank oak flooring throughout. Upon entering the grand foyer enjoy views of the art work and stunning chandeliers that stretch throughout the home to the yard. There is a separate Home office/Den offering full privacy to use for entertaining or for conducting business with a wet bar and wine cooler in the neighboring hall way. The gourmet kitchen is fully equipped with custom cabinetry, stainless steel appliances including double Miele dishwashers and a marble center island for gatherings, and serves the sun bathed breakfast room. Dine in the grand sun filled great room with spectacular ship-lap 20' ceilings with French doors leading to the serene views of the pool and yard. This integrated

This beautifully restored historic 3-bedroom Victorian blends timeless charm with modernist sophistication, nestled in the very center of Bridgehampton’s coveted hamlet. Every detail of this spacious residence has been sensitively renovated to reflect a high standard of design and comfort, combining original character with sleek, contemporary updates. The main floor features a sunlit living room, a windowed dining area, and a stylish kitchen outfitted with brand-new appliances. A full bathroom and a delightful sunroom—perfect as a home office, library, or serene summer retreat—complete the first level. Upstairs, three bright bedrooms share a renovated full bath. The generous king-sized primary bedroom includes an adjoining ensuite bathroom. Outdoors, enjoy coffee or evening rosé on the inviting front porch overlooking a lush garden, or entertain in the elegant gravel patio surrounded by manicured hedges—an ideal summer setting. Just one block to Bridgehampton’s shops, art galleries, s

Tucked away amid the dunes of Southampton's coveted Oceanfront district of Meadow Lane awaits a traditional cedar-shake Cottage. Perched upon a privately landscaped 1.75-acre parcel that comprises 125 +/- ft of direct Oceanfront. A spellbinding atmosphere defines this seaside enclave; the location allows for captivating vistas of the coastline's sandy beaches and a sense of privacy and seclusion, an ever-rare commodity. Abundant foliage instills an opulent quality into the property's tiered outdoor grounds, which feature a heated saltwater pool, spa, and pool cabana, along with a mixed-media tennis court, multilevel decking overlooking the Atlantic Ocean, and a private walkway over the dunes. This Meadow Lane home makes no concessions when it comes to indulgence. Prime location along Meadow Lane offers convenient access to Main Street, Jobs Lane, and surrounding Beach and Tennis clubs, while the heliport awaits one (1) +/- mile(s) down Meadow Lane—50-amp outlet for electric cars with h

Recently updated 6 bedroom / 4.5 bathroom house with an oversized diving pool and a private tennis court centrally located on lush 4 acres in Water mill at 249 Roses Grove Road. The soaring living room and a fully stocked Poggenpohl kitchen open up into a wonderfully set up oversized deck & pool surrounded by lush greenery and hidden from the road at the end of a 150 foot driveway. All house systems including water filtration, central AC, heating, pool heating, and more have been recently updated or replaced with no expense spared. On the other side of the house you find your private clay tennis court, ping-pong table, and a cleared area with a fire table and 6 Adirondack chairs. Inside, there are 2 Primary suites with a private bathroom each, optimally located at the opposite ends of the house. There are a total of 6 bedrooms and 4.5 bathrooms perfectly positioned to house in-laws, 2 families or to separate hosts and guests for optimal privacy. 5 Large screen TVs (60-85 inches) are fe

Spend your summer in North Sea and be the first to rent this newly renovated and tastefully decorated home with brand new pool! This home has multiple bonus rooms and plenty of places to rest your head and relax your mind. Minutes to Southampton Village! The house features vaulted ceilings with skylights allowing a bright and open living area. Cook a great meal in the brand new, fully stocked kitchen. Rinse off the sand and salt in the outdoor shower and relax on the brand new deck in the back, perfect for BBQs and relaxing with friends. In addition to the bedrooms, there is a home office or quiet reading room. This is your perfect spot to enjoy a Hamptons summer

Spend your summer in style at this beautifully renovated Hamptons vacation rental, ideally located near North Sea Park and just minutes from the world-famous Southampton Town beaches and Southampton Village. This spacious and sun-filled 4 bedroom, 3.5 bathroom home offers the perfect blend of comfort, luxury, and convenience for an unforgettable summer escape in the Hamptons. Inside, you'll find an open-concept layout with a newly done kitchen that flows effortlessly into a naturally lit dining area, creating a seamless space for entertaining. The double-height living room features a striking wood-burning fireplace, making it the perfect place to gather and unwind. The home also includes a partially finished basement, a full-size washer and dryer, a 100-bottle wine refrigerator, and additional access to an oversized garage. Step outside into your own private oasis, where mature landscaping surrounds a newly redone heated and saltwater pool. An outdoor shower adds a touch of convenience

Escape to this beautifully appointed 4-bedroom Southampton Village home featuring a gunite pool and access to a community tennis court. Perfectly designed for both relaxation and entertaining, the home offers an ideal Hamptons getaway. The first floor boasts a spacious living room, dining room, and a well-equipped kitchen for all your culinary needs. A cozy den with French doors opens directly to the pool area, creating seamless indoor-outdoor living. A full bath, half bath, and washer/dryer complete this level for added convenience. Upstairs, the primary ensuite bedroom offers a private retreat with its own attached office, perfect for work-from-home flexibility. A guest ensuite bedroom and two additional guest bedrooms with a hall full bath ensure plenty of space for friends and family

Looking for a traditional summer getaway? This traditional two-story home offers 4 bedrooms, 4.5 baths, open living room with fireplace, chef's kitchen and sunroom. There is a wonderful pool area great for entertaining. Relax on the beautiful covered front porch

This charming 4-bedroom, 2.5-bathroom home offers the perfect blend of comfort, convenience, and seaside serenity. As you step inside, you'll notice the beachy feel that permeates every corner of this home. The spacious living areas invite you to relax and unwind, with ample room and a well-appointed Chef's Kitchen for gatherings and entertaining. Each bedroom is designed to offer tranquility and functionality, featuring windows that flood the rooms with natural light and offer glimpses of the surrounding natural beauty. Venture into the backyard, and you'll discover your own private paradise. A gunite saltwater pool offers a refreshing escape during hot summer days, accompanied by an outdoor shower. The Dave Allison Park is just a short stroll away. Its playground and sandy community beach are ideal destinations for picnics, games, and waterfront fun. East Creek Beach, a private haven, is also within walking distance, offering secluded shores and tranquil waters for swimming and sunba

This amazing new construction 6400 sq ft home exudes luxurious modern living with all the latest smart home wiring devices. Perfectly positioned, facing southwest the home is drenched with unrelenting natural light, all day. This expansive, open-concept home offers a gourmet chef's kitchen, island seating, breakfast area, formal dining room, and a considerable living/family room with sliding glass doors that open up to the beautifully landscaped backyard, inground gunite 20x40ft pool, and conveniently designed patio creating a private oasis or the perfect space to entertain. The generous master suite is fully equipped with a walk-in closet and custom shelving. Five additional spacious bedrooms, five full bathrooms and two half bathrooms. The lower level is fully finished with media room, exercise room with sauna, and additional storage areas. Virtual Tour

Escape to the beauty and tranquility of Sagaponack with your family and friends. Enjoy the newly renovated, designer-decorated, spacious 5,100 sq ft, 5-bedroom, 5-bathroom house, which sleeps up to 10 people in comfort. The 1.7 acre property features a backyard paradise with large pool, built-in hot tub and fire pit in a large bluestone patio stretching the entire length of the house. The property is in a superb location in one of the most sought-after zip codes in the Hamptons. All destinations are easily accessible. It is a 7-minute drive south to the Atlantic beaches (15 minutes by bicycle); 7-minute drive north to Sag Harbor village; and 6-minutes to the center of Bridgehampton village. East Hampton village is 12 minutes away. The award-winning and luxurious Wolffer Estate Vineyard is only a mile away. The Sagaponack Farm Distillery is even closer. The house is privately located on a long beautiful residential street of magnificent homes. The location is ideal because virtually any

Welcome to your Hamptons oasis, conveniently located within close proximity to the bay, Southampton Village and Sag Harbor! This four bedroom, four bath home is sited on over 3/4 of an acre and features a brand new kitchen, updated primary suite, brand new furniture and a finished lower level. The exterior boasts ample decking for indoor/outdoor living as well as a gunite heated pool and outdoor shower. Book your appointment to view today!

Show stopping new construction in the heart of Southampton Village, perfectly positioned just one block from town, offering an effortless blend of luxury, convenience, and lifestyle. Wrapped in a timeless cedar-shingled exterior, this residence seamlessly merges traditional Hamptons architecture with modern, light-filled interiors across 7 bedrooms and 7.5 baths—each thoughtfully designed with radiant heat, including the attached 2-car garage. The home’s open-concept layout is designed for both elevated entertaining and everyday living, with expansive gathering spaces that flow effortlessly from one room to the next. A custom chef’s kitchen with premium appliances and bespoke cabinetry anchors the main level, opening into a sun-drenched great room with fireplace and refined finishes throughout. The formal dining area, complete with a wet bar, connects to a grand paneled foyer and a junior primary suite, while a striking staircase leads to the second level. Upstairs, the primary suite i

This fabulous, newly constructed home is now available for rent at any time of year! The home boasts 6 ensuite bedrooms, 6.5 bathrooms, two large living rooms each with a fireplace, a beautiful gourmet chef’s kitchen, large island with seating, breakfast area, and formal dining room. The finished lower level offers a game room, home gym with floor to ceiling mirrors, and a home theatre with 8 reclining large chairs. The spacious yard is fully equipped with a heated in-ground pool, outdoor shower, large outdoor covered bar, covered deck with outdoor fans as well as flush mounted ceiling heaters providing the perfect place for entertaining. With quick and easy access to Village beaches and Main St restaurants and shops this incredible rental opportunity should not be missed!

This beautiful, seven bedroom, six bath new construction features an incredible open-concept floor plan with a generous gourmet chef's kitchen, attached dining area, living/family room and fireplace. The upper level houses five bedrooms, and three full bathrooms. The beautifully designed master suite includes a private balcony, and master bath with a large walk-in waterfall shower and stand-alone soaking bathtub. Large modern black windows and three sets of sliding glass doors allows an astonishing amount of natural light to flow throughout the main floor. Outside the sliding glass door is a covered porch that leads down to a stunning patio with an outdoor dining area, fireplace, and in-ground heated gunite pool. A detached pool house further reassures entertaining potential of this property with hardwood floors, air conditioning, a mini kitchen area and full bath. Lastly, this house has an amazing finished basement. You don't want to miss out on this incredible opportunity! Virtual To

Located in the exclusive community of The Fields Southampton, this exceptional Paramount residence offers approximately 6,250 square feet of luxury living space. With seven bedrooms, six full baths, and two half baths, it is perfect for full-season or year-round rental. The community boasts private tennis and basketball courts, as well as a scenic walking trail. Upon entry, a grand double-height foyer leads to open living areas, including a family room with a fireplace, a breakfast area, and a meticulously designed Chef's kitchen. Glass sliding doors open to a bluestone patio with an outdoor kitchen and a heated gunite pool. Other features include a den/TV room, a junior primary suite, a mudroom, and a two-car garage. Ascending to the upper level, a generously sized primary suite awaits with a walk-in closet and opulent bath. The bath includes a soaking tub, steam shower, separate shower, double quartz vanity, heated mirrors, and radiant heated flooring. Additional bedrooms on this lev

Handsome two-story traditional comprises nearly 6000 ft.2 of living space with carefully designer-curated rooms. The estate offers a private setting behind the hedges in an unrivaled location. It is a secluded four-acre corner lot on Little Plains Road and the storied Gin Lane, one block from the Atlantic Ocean. Virtual Tour

Experience the very best of Hamptons Village living with this charming cedar-shake home! Perfectly situated on a picturesque.4-acre lot, the main residence features a welcoming first floor with a kitchen, dining room, living room, and a half bath. Upstairs, you’ll find two comfortable bedrooms and a full bath. Designer finishes throughout, from unlacquered brass hardware to handcrafted Moroccan Zellige tiles in the spa-like primary and pool house bathrooms. Step outside to your private oasis, complete with an L-shaped pool, cold plunge, sauna, outdoor shower, and lush landscaping. A spacious two-story, 750-square-foot pool house serves as the ultimate retreat, featuring an upstairs bonus room, full bath, its own porch, private patio, and serene views of the beautifully landscaped grounds. Located just moments from the heart of Bridgehampton Village, this property provides effortless access to world-class shopping, exceptional dining, and the pristine ocean beaches that make the Hampton

Available for any two weeks for $53,000.00 from Wednesday, July 1, 2026 - Monday, September 7, 2026.* Situated in one of Southampton Village’s most desirable locations and masterfully designed by acclaimed architect Hank Flynn, this distinguished residence seamlessly blends timeless architecture with modern comfort. The home offers five generously proportioned bedrooms and three and two-half baths. A beautifully appointed eat-in kitchen flows effortlessly into the inviting family room, while a dramatic double-height living room and formal dining area create an impressive setting for entertaining. The finished lower level provides exceptional additional living space, featuring a beautiful media room and luxurious home theater, a spacious recreational/game room, a laundry room, and a half bath—creating the perfect environment for relaxation and entertainment. A spacious third-floor playroom or private office offers exceptional flexibility—ideal for today’s work-from-home lifestyle—and is

This inviting 4-bedroom, 3+ bathroom home is situated on nearly an acre of land. On the first floor, you'll find a newly renovated kitchen (completed in winter 2024), a cozy sitting/living area, a dining room, and a bonus room that could be used as an office or flex space. Upstairs, the primary bedroom is accompanied by three guest bedrooms. A finished lower level with bonus room gives plenty of indoor living space for extra guests that stop by. The backyard oasis is a relaxing retreat with a heated pool, full bar area with kitchen space and multiple lounge areas to enjoy the hamptons summer sun! This home has all the amenities for the most amazing summer you have had yet!

Tucked away on a cul-de-sac in a private waterfront community this 2500 sq ft residence is set on a full landscaped acre and is just half mile stroll to bay beach. First floor primary (King) with master en-suite bathroom renovated Winter 2022 with double vanity, 72 inch soaking tub and spa shower. Additionally the main level includes both a living room and a den (or can be converted to additional office space) and great room that includes open-style kitchen with island, dining table, sitting area and sliding doors to the backyard patio. The second floor includes second bedroom (two twins), guest bed (queen), full bath (renovated 2022) and bonus room perfect to house extra company or set up an additional lounge or work space. Outdoor area includes custom built 50 by 20 ft gunite pool with marble dusted bottom and automatic retractable solar safety cover. A large grassy area extends beyond the pool. Includes 6 chaise lounges, outdoor dining table for six, bistro table for four, fire pit

Show stopping new construction in the heart of Southampton Village, perfectly positioned just one block from town, offering an effortless blend of luxury, convenience, and lifestyle. Wrapped in a timeless cedar-shingled exterior, this residence seamlessly merges traditional Hamptons architecture with modern, light-filled interiors across 7 bedrooms and 7.5 baths—each thoughtfully designed with radiant heat, including the attached 2-car garage. The home’s open-concept layout is designed for both elevated entertaining and everyday living, with expansive gathering spaces that flow effortlessly from one room to the next. A custom chef’s kitchen with premium appliances and bespoke cabinetry anchors the main level, opening into a sun-drenched great room with fireplace and refined finishes throughout. The formal dining area, complete with a wet bar, connects to a grand paneled foyer and a junior primary suite, while a striking staircase leads to the second level. Upstairs, the primary suite i

Set on a private half acre in Southampton, this beautifully renovated contemporary offers Hamptons living just minutes from bay beaches, Water Mill, Sag Harbor, and Bridgehampton. Extensively updated in 2025, the property features refreshed modern interiors, a brand new heated pool, lush landscaping, enhanced outdoor living spaces, and a fully fenced backyard designed for privacy and entertaining. The home offers approximately 1,500 square feet across two levels, plus 600± square feet of finished lower-level space, with 3 bedrooms, 2.5 baths, and an attached 2-car garage (with Tesla charger). Inside, soaring ceilings, exposed wood beams, crisp white finishes, oversized windows, and abundant natural light create a warm, modern coastal aesthetic. A dramatic double height great room is anchored by a fireplace with shiplap detailing and opens through a wall of glass doors to an expansive wraparound porch, creating seamless indoor-outdoor living. The adjoining chef's kitchen features stainl

Located in the coveted Southampton shores community this five bedroom, two bathroom has all you need for a summer getaway. Location can't be beat as this is the second home from the entrance of the private community beach and just up the road from the community tennis and basket ball courts. This home features three bedrooms on the second floor with full bath and two additional guest bedrooms and full bathroom on the first floor. Lots of privacy for all with this home and don't forget to enjoy your time on the large back deck perfect for summer night bbqs. Call today for more information

Light-filled, beautifully renovated and updated four bedroom, two and a half bath home on a just-shy half acre in Shinnecock Hills isstylish and flooded with natural light. Open upstairs living areas feature a wall of energy-efficient glass doors opening to an upperdeck, and flow among a living area, formal dining area and beautiful kitchen with new cabinets, granite countertops and stainlesssteel appliances. All new baths feature marble flooring and walls, and new fixtures. Additional upgrades include new hardwoodflooring on the upper level, updated electrical work, new front roof, all new paint, new A/C and heating system, smart wiring for Sonos, high speed internet and cable lines. Extensive decking surrounds the heated pool wonderful gardens. The house is also equipped with EV charging for electric vehicals. Making this such a sought after location as you have Meschutt bay beach and Coopers ocean beach, which offers daily parking, all within 10 minutes

Ideally located between Southampton Village and Hampton Bays, this south-facing Shinnecock Hills ranch is the perfect summer escape. Set on.60 acre on a quiet street, the home offers simple, comfortable living with easy access to both ocean and bay beaches. With three bedrooms and two full bathrooms, there’s plenty of space to relax and unwind. The bright and open gathering/dining room is the heart of the home, featuring vaulted ceilings with wood beam detail, a wood-burning fireplace, and sliding doors that lead out to a large deck and private backyard—ideal for summer lounging and entertaining. The kitchen is well-equipped with stainless steel appliances and granite countertops, making at-home meals a breeze. A new composite deck with sleek post-and-wire railings adds to the home’s relaxed, stylish feel. Whether you're spending the season exploring the Hamptons or just unwinding close to the coast, this charming home has everything you need for an effortless summer