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Holiday Rentals with Pools in Bridgehampton

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    $2,769 Average
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    11 Matching Rentals in BridgehamptonView all 34 rentals
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    Travellers to Bridgehampton are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    5 Bedrooms, Sleeps 10Quick View
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    4 Bedrooms, Sleeps 8Quick View
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    4 Bedrooms, Sleeps 8Quick View
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    3 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Internet Access
    • Parking
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 7 March 2017
    On a quiet street, in a perfect location. My family stayed here for presidents weekend. We loved the modern look of the house and it had everything we needed. The house is...
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    About this property
    Bridgehampton White House RATES INCLUDE THE FOLLOWING: Electric consumption, cable TV & wi-fi, propane consumption, telephone, trash removal, lawn & pool service and heating of pool to 85 degrees between Memorial Day and Labor Day. OVERVIEW OF HOME: 3 bedrooms 3 bathrooms Finished Basement with TV...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 10Quick View
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    • Patio
    • Private Garden
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Secure Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate, newly renovated home is conveniently located on a quiet cul-de-sac walking distance from the center of Bridgehampton Village and and a quick bike ride to the beach. Sleeping quarters consist of 4 bedrooms and 3 full baths. The home has central air conditioning. The master bedroom...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 9Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On a quiet shy 2 acre beautiful parcel adjacent to hundreds of acres of town reserve sits this updated light filled home with sweeping lawn, and reserves on 3 sides for complete privacy. Spacious with 4 bedrooms and 3.5 baths,Two masters with king beds and private baths, two additional bedrooms one...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    11 Bedrooms, Sleeps 22Quick View
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    • DVD Player
    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A total of 15,000 sq.ft. encompasses 11 bedrooms and 11.5 bathrooms including the main house and a luxurious guest house both with three floors of superbly crafted living space. Amenities include all-weather tennis, an over sized 25' x 55' heated gunite pool, fully finished lower levels in both...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 11 Bedrooms, 9 Bathrooms, Sleeps 22
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    5 Bedrooms, Sleeps 10Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous four bedroom, four bathroom home is nestled in Bridgehampton, close to town. The home is bright and sunny, with a large heated pool. Seperate Guest/nanny...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home features four bedrooms and four baths, and fantastic chef's kitchen, and large bright living spaces. The guesthouse includes two additional bedrooms and a bath. Expansive open lawns and a heated gunite pool complete the property. This south of the highway, shingled masterpiece is close to the...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 14Quick View
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    • Wi-Fi
    • Balcony
    • Satellite TV
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful villa is 5 bedrooms, 3 bath with a garage, Fantastic pool, and yard, and is just minutes from the town of Bridgehampton, Southampton and the beaches! 1 week villa rental preferred. This beautiful villa is 5 bedrooms, 3 bath with a garage, Fantastic pool, and yard, and is just...
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    Bridgehampton, Hamptons 11968
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 8Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 4 bedroom home backs to preserve and is located just north of the village with an open floor plan and wonderful light and high ceilings throughout. Main floor has guest bedroom and bath, living room with fireplace and double height ceilings, separate dining area and eat-in kitchen, which...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    • Washer
    • Housekeeping Included
    • Grill
    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    1 Night stay is available. Please inquire negotiable rates for longer stay. BOOK 2 NIGHTS AND STAY 3RD NIGHT FREE up until May 1st. (Excludes Free Fri or Sat nights.) Each season brings fun festivities! Seasonal rates reduced, please inquire to negotiate! Fenced in backyard. Minutes from Hampton...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    • Hot Tub
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    Pet friendly
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    About this property
    Traditional two-story featuring 4 bedrooms, 3.5 bath, gourmet kitchen, Jacuzzi and heated pool. This home is a perfect summer getaway. You do not only get to enjoy your summer vacation with the beaches, good food and shopping nearby, but the house itself offers you amazing amenities to enjoy summer...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    • Private Garden
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful contemporary home set on 1.6 private idyllic acres. <BR>Perfect for families with children as well as entertaining. Beautiful Bluestone deck and patio.<BR>Walk to town, near beaches. Easy drive to Sag Harbor, Southampton and East Hampton. Right by Hampton Classic and Polo grounds....
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Beautiful sundenched hamptons property recently renovated quiet and private yet centrally located to all ocean and bay beaches, shopping and transportation. Bike to beaches, towns of Bridgehampton and Sag Harbor. Vineyards and farm stands just up the street. Dead end street location great for kids...
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    Bridgehampton, Hamptons 11936
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 10Quick View
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    This 5 bedroom, 4.5 bath home is located on .67 acres in Bridgehampton north. New floors throughout, new kitchen, Pool table in basement with 40 inch plasma TV, indoor and outdoor speakers and pull out sofa bed. You can relax by the heated pool and new outdoor shower after spending the day on the...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 6Quick View
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    Bridgehampton Summer Beach rental with heated gunite pool, close to Channing Winery and conveniently located between Bridgehampton and Sag Harbor Villages in the heart of the horse country. The house is a convenient five minute drive to either town and less than a ten minute drive to the beach. The...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, Sleeps 14Quick View
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    This 10,000 + sq. cedar-shingled gambrel style home located on the most desired street in Bridgehampton sits across from a pristine reserve and incorporates all contemporary estate features. The private gated entry gives way to one acre of lush gardens offering privacy and tranquility for all to...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 7 Bedrooms, 11 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 8Quick View
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    Impressive Bruce Nagel designed and professionally decorated Bridgehampton Village home with dramatic entry foyer with sweeping stairway, 2 master bedrooms overlooking the expansive rear yard and 2 guest bedrooms with an exquisitely outfitted bath,formal living room with fireplace, family room with...
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    Bridgehampton, Hamptons 11937
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    7 Bedrooms, Sleeps 14Quick View
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    About this property
    Romantic & elegant home. Totally renovated. Original woodwork, fireplaces & doors; wrap-around porch; back patio; carport; pool house w/toilet, sink, frig, outdoor shower; 1st fl: formal LR, sitting room, formal DR, butler's pantry. large country kitchen, bathroom & laundry room; 2nd FL: Master...
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    Bridgehampton, Hamptons 11937
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, Sleeps 6Quick View
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    Spend your summer in this bright, open and airy Traditional with large entertaining space all centered around a beautiful stone fireplace, spacious master bedroom with bath and two additional en-suite bedrooms . Close to village of Bridgehampton and ocean beaches. Private half acre surrounds the...
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    Bridgehampton, Hamptons 11937
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Enjoy this Magical 3 Bedroom, 3 Bath Cottage. Master Suite with Sitting Room. Exquisitely Landscaped with Deck, Pool and a Wisteria Draped Pergola to Dine Under. This beach cottage is beautifully landscaped in a .5 acre and close the Bridgehampton beaches and village. The house has a radiant feel...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, Sleeps 12Quick View
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    • Ocean Views
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    Pet friendly
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    About this property
    Spend your summer in this beautiful 6 bedroom, 7 bath home and enjoy endless views to the ocean and Mecox Bay. Featuring a light filled interior with a living room with fireplace, dining room with gorgeous views and an eat-in kitchen, this home is the perfect summer get-away. Water side heated...
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    Bridgehampton, Hamptons 11976
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    8 Bedrooms, Sleeps 16Quick View
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    This spacious 7000 square feet home features 8 bedrooms, and 8.5 baths. The high-ceiling foyer leads to its spacious living room. It is located in a private gated community this home offers views of the lakes and a heated pool on 2.25 acres. Kellis pond is of Hamptons amazing water lakes with...
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    Bridgehampton, Hamptons 11976
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 10Quick View
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    Enjoy your Summer in this 5 Bedroom, 3 Bath Post Modern Home Situated Conveniently near Bridgehampton and Sag Harbor Villages. This Home Boasts a Large Open Floor Plan, Outdoor Decks and...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    Located south of the highway on a private street, is this elegant 4 bedroom 5 1/2 bath estate on 4 manicured acres. Previously featured in prominent publications, this Beautiful and professionally decorated traditional and spacious home boasts 8 fireplaces, a state of the art country kitchen,...
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    Bridgehampton, Hamptons 11968
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 10Quick View
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    Beautiful Post Modern built in 2009 with 5 bedrooms, 4.5 bathrooms, gourmet kitchen, spacious open interior with double height ceilings, stylish furniture, tennis , 18x50 gunite pool and pool house, large...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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    Abutting a 13 acre horsefarm - this spacious six bedroom home has room for all your loved ones! Open living areas and multi windowed areas allow the light to stream in. There is master and 3 guests in main house and a separate wing has additional master suite and guest bedroom for additional...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    7 Bedrooms, Sleeps 14Quick View
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    7500 square feet of the Finest Craftmenship Throughout. Gourmet Eat-In-Kitchen with Sitting Room, Dining Room, Library, Living Room with Fireplace, Master Suite with Fireplace and Separate Sitting Room all on the First Floor with 11' Ceilings. Second Floor has Six Elegant En Suite Bedrooms. There...
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    Bridgehampton, Hamptons 11976
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    5 Bedrooms, Sleeps 10Quick View
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    Situated on one of the famous streets south of the highway in Bridgehampton, this beautiful property is 2.25 acres of gorgeously landscaped with a Gunite pool, and a tennis court. This 5 bedroom home has a gourmet kitchen, living room, family room, formal dining, large master suite with office, 6.5...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 10Quick View
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    Beautiful traditional close to ocean beaches. Featuring 6 bedrooms, 6.5 baths, a library, 2 fireplaces, formal dining room, chef's kitchen and a tastefully furnished cathedral living room. Beautifully landscaped grounds include a heated gunite pool and lovely outdoor dining spaces. House just...
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    Bridgehampton, Hamptons 11976
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    6 Bedrooms, Sleeps 12Quick View
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    This Bridgehampton six bedroom offers everything you want in a summer vacation. The house has been recently renovated from top to bottom. The backyard offers tennis and an amazing pool for entertaining. A...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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    7 Bedrooms, Sleeps 14Quick View
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    7500 square feet of the Finest Craftmenship Throughout. Gourmet Eat-In-Kitchen with Sitting Room, Dining Room, Library, Living Room with Fireplace, Master Suite with Fireplace and Separate Sitting Room all on the First Floor with 11' Ceilings. Second Floor has Six Elegant En Suite Bedrooms. There...
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    Bridgehampton, Hamptons 11976
    Holiday Rental House - 7 Bedrooms, 8 Bathrooms, Sleeps 14
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    2 Bedrooms, Sleeps 4Quick View
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    • Parking
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    • Private Garden
    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Lovely Hamptons Cottage. 2BR with w/d on site and plenty of off street parking. Lovely ponds and peaceful environment. Central to accessing all of the Hamptons. Internet, Cable TV, Wifi, contemporary design. New furniture. Full kitchen. Outdoor patio. Lovely landscaping. Nature walks. Enjoy a...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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