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Bridgehampton Holiday Vacation with Pools

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    $1,627 Average
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    Travellers to Bridgehampton are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    11 Matching Rentals in BridgehamptonView all 39 rentals
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Designer Decorated 3 Bedroom in Prime Location Heated Salt Water Pool1 / 21
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bridgehampton South Traditional. 5 bedrooms (including a master both upstairs and downstairs), 4 baths, and a new kitchen with brand new marble island. The lucky tenant of this property will enjoy elegantly appointed principal rooms, further enhanced by a wonderful open and circular flow. Sleeping...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    11 Bedrooms, 9 Bathrooms, Sleeps 22 Quick 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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 11 Bedrooms, 9 Bathrooms, Sleeps 22
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious, renovated 5-bedroom, 4-bath home is on a secluded 1/2 acre, with a 200-foot private driveway leading to the wonderful, bright residence. The house backs onto a community reserve, so there is complete privacy in the pool, decks, and backyard. On the main level, there are 4 bedrooms...
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    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy this 4 Bedroom, 2.5 Bath Post Modern Home with Screened in Porch and Heated Pool. Conveniently Located between Sag Harbor and Bridgehampton, Beautifully and comfortably decorated, a few minutes to restaurants and the beaches! This is the best location you can get with lots of rooms to relax...
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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Bridgehampton, Hamptons 11932
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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