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Holiday Rentals in Hamptons

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    Travellers to Hamptons are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 279 Rentals in Hamptons
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    Hamptons Beach House, steps to beach.1 / 6
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hip & Stylish East Hampton Getaway1 / 24
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Village Fringe glassy Modern with Pool and Tennis1 / 19
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2017
    My family was looking for a quiet house to relax in a beautiful setting, and we had just this house. This sunny, bright, clean and pleasant...most of all, luxurious house with...
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    About this property
    SPECIALS: July 21-31 (=2 weekends!) at only 10k plus cleaning and pool heat (=10.75k Total) Peace and quiet awaits in this modern house on the village fringe, featuring a first floor master with walk in closet, wonderfull spa-style master bath, flatscreen TV and direct access to the pool and...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is 2 weeks during High Season unless you see an availability between rentals. During the off season 1 week rentals may be possible. This elegant 6000 square foot home...
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    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Private Garden
    • Satellite TV
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, new space is nicely appointed with modern fixtures and finishes. High ceilings, clean and bright. Walk to the bay beach for stunning sunsets. New furniture, linens, towels, etc. Contact us for weekly, monthly or seasonal pricing. This beautiful, new space is nicely appointed...
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    11963, Sag Harbor, Hamptons
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is perfectly located. It has a 1 Bedroom cottage with a private deck. It's wonderfully cozy and a perfect place to come back to after adventuring around town or just lounging on the beach. Southampton village 3 min. Just 6 minutes away is Cooper's Beach, rated one of the best beaches in...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Montauk Modern with Heated Salt Water Pool1 / 21
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Secure Parking
    • Balcony
    • Washer
    • Grill
    • Wi-Fi
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Great house, great host. The salt water pool is amazing. Would definitely book again and recommend to friends.
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    About this property
    The Montauk Modern Compound is set up like a traditional bed and breakfast. The design elements, local art and the super clean environment is complimented by the native gardens and landscape. A little private oasis. The Montauk Family Compound has 3 different living zones. Currently available (all...
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    11954, Montauk, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    10 Minutes to Ocean Beaches. Poolside1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Satellite TV
    • Hot Tub
    • Patio
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2016
    We stayed for four days. The house is very nice and just as depicted in the photos. Pam was very gracious and very accommodating. She was very flexible with arrival and...
    Reviewed 5 August 2016
    Very cute and homey house, great hosts and a good location in the Hamptons. Close to Sag Harbor and East Hampton and close to the water. The pool is really nice and clean and...
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    About this property
    Spend your summer relaxing by the heated pool or enjoying the close beautiful bay beaches of the North West Woods or just a quick car ride to a sandy ocean beach of the Hamptons. This charming air-conditioned home is sited on a privately landscaped half acre property. An open light filled great...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Hampton Bay Home Getaway -- 2500sqft, 3br (sleeps 12) - 3 full bths & 1 half bth (HUGE Master Suite), sitting rm w/fp, living rm, dining rm, eat in kitchen, billiard room & game room -- Large Backyard w LARGE in-ground heated pool, wood burning fire pit, barbecue grill, sand volleyball...
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    Location Information
    11946, Hampton Bays, Hamptons
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Cottage by the Sea1 / 5
    (6)Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Satellite TV
    • Parking
    • Balcony
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2016
    Great location! Cottage was also very clean and well kept, perfect for our family beach vacation. Will definitely go back
    Reviewed 31 July 2016
    The cottage was very clean, well equipped and inviting. The location was terrific, only a block from the beach and town. We enjoyed the open floor plan and the lovely yard...
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    About this property
    This newly renovated cottage in the heart of Montauk is 1000 feet from the ocean beach. It is a free standing cottage with a large back yard for entertaining. It has been in our family for over 70 years. It has central heat and air, with hard wood floors and modern. It is located between the...
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    11954, Montauk, Hamptons
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Internet Access
    • Grill
    • DVD Player
    • Washer
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Let this stunning 3-bedroom, 2-bathroom vacation rental home jump start your East Hampton retreat! Offering fantastic amenities, accommodations for 6 and an unbeatable location near East Harbor, this unit leaves little to be desired! THE PROPERTY From the moment you arrive at this luxurious home,...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Hampton Dream House 'Serendipity' - Great Buy1 / 7
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2017
    My wife and I stayed at this lovely place last week. Our two sons and their girlfriends also stayed. We had a fantastic time. The heated swimming pool was absolutely fabulous...
    Reviewed 10 June 2016
    My wife and I stayed in this lovely house in May 2016.A lovely quiet area approx. 1/4 mile off the main road so supremely quiet.It was very well furnished and equipped and...
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    About this property
    Enjoy this sophisticated, newly renovated, three-bedroom, three-bath contemporary on one of the premier lanes near Jackson Pollack's house in East Hampton. Twenty-four-hundred square feet with oak flooring throughout. Great light in the beautifully designer decorated double height living/dining...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Immaculate 4BR Southampton House w/Private Pool!1 / 32
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    My husband and I stayed here over the fall for the long weekend. The house and décor were truly beautify, exactly what you’d think of for Hamptons style. It had big bay windows...
    Reviewed 23 May 2017
    Came here for a couples getaway with my wife and some friends. Had a great time and ended up inviting some friends from CT to join us when we realized the house sleeps many more...
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    About this property
    Experience the exquisite relaxation of upper Long Island, New York by staying at this luxurious 4-bedroom, 4-bathroom Southampton vacation rental home, which sleeps 8! With incredible upscale amenities, an alluring private pool, wraparound deck with bay views, exclusive access to a pristine natural...
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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located a few blocks from Wollfer Vineyard and blocks away from the town of Sag Harbor. You will have all the privacy you want. Enjoy a beautiful built in pool. The home is clean, stylishly decorated, and close to gorgeous beaches. Work out room, everything! The location...
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    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Satellite TV
    • Hot Tub
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Be close to everything the Hamptons has to offer while getting away from it all in your little piece of paradise.! You'll be a mere 1 mile away from the ocean beaches of and in close proximity to the Hampton Village of Southampton - with its exciting selection of restaurants, shops, movie theater,...
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    11968, Southampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sunshine Bungalow Shelter Island Retreat1 / 26
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Having spent just a day at Sunshine Bungalow, I still couldn't recommend this place highly enough. If you are planning a quick weekend getaway or just looking for a nice...
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    About this property
    '1 Master bedroom with King size bed and another bedroom with 2 Queen size beds. Sleeps 6. Newly renovated with top of the line furniture, this house is close to: world renown Sunset Beach restaurant by famed owner Andre Balazs, Commander Cody's, Marie Eiffel Dockside Market, Mashomack Preserve,...
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    11964, Shelter Island, Hamptons
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    North Fork 5 bed room home with forever farm view1 / 37
    (9)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Satellite TV
    • Grill
    • Wi-Fi
    • Secure Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2017
    This is a really cute house with a lot of bedrooms. The common areas are cozy but the backyard had plenty of room for a large group (10 people) to hang out and play yard games...
    Reviewed 7 May 2017
    Not a typical reviewer of places I stay, but this place wasn't typical. Bruce was a pleasure to work with. The location was excellent on a quiet street near Riverhead. Great...
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    About this property
    Five bedroom home with central air conditioning.This home has modern kitchen pillow top bed a large 52" plasma tvs.This home has tv in master and queen br bbq grill,12 gazebo with a tumbled stone patio.The patio has a table with seating for eight The view from the gazebo area is about one mile...
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    11931, Aquebogue, Riverhead
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Satellite TV
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in all that East Hampton has to offer at this stunning 4-bedroom, 3-bathroom vacation rental house that comfortably sleeps 10. Situated on 2 acres of fenced land with a playground, lush grass, and 50-foot pool with 10 chaise lounge chairs, you'll feel as though you're staying at a...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    East Hampton Family Retreat with Cottage1 / 41
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2015
    The best vacation ever! The main house, the cottage, the pool, the kitchen, the cabana, everything met or exceeded our expectations. The kitchen was stocked with everything...
    Reviewed 27 November 2014
    Beautiful property with plenty of space to relax. The owner was extremely helpful and professional. Also great location as there are many fun things to do close by.
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    About this property
    Please note: WEEKLY / MONTHLY ONLY IN JULY, AUGUST, THUR LABOR DAY! (HAVE THE LAST WEEK OF JUNE OPEN, THE 25 - JULY 2ND) Please note! The rates listed are off season only, higher Memorial Day to Labor Day. Beautiful wooded property and private retreat located between the ocean and bay, surrounded...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Porch
    • Central Heating
    • Secure Parking
    • Washer
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CLEAN, QUIET, LARGE BEDROOM - GREAT DEAL - AFFORDABLE PRICE! One Queen Size bed that accommodates Two people Perfectly! Bright and Airy room! Large 52in Hunter Ceiling fan directly above the bed as well as soothing cross breezes from the oversized windows that overlook the sunny front garden....
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    11937, East Hampton, Hamptons
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Hot Tub
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is perfectly located in Southampton. It is a 4 Bedroom, sleeps 10. If you have been wanting to visit The Hampton's for the first time this house is the perfect choice since its perfectly located in the heart of the Hampton's, just a three minute drive to the village with all the...
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    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Patio
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With the ultimate prime Hamptons location, and the comforts of home, this vacation rental is an excellent value for all types of friends and family retreats. The outdoor areas are newly designed and rebuilt with 3,100 square feet of mahogany decking. Right outside the great room there is a new...
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    11962, Sagaponack, Hamptons
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    Post Modern Quaint Home Near  Beach1 / 71
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Satellite TV
    • Patio
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Highly recommend this house. Clean, large enough for to fit our 2 families very comfortably. Owner was very responsive.
    Reviewed 3 September 2016
    It is a very big and clean house with a big pool. Our families are so enjoy the time of staying here, and the homeowner is very helpful before and during the stay.
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    About this property
    Immaculate four bedrooms, three full baths sleeps 8-10. Full gym, pool and jacuzzi nestled away in prestigious Red Cedar Ridge. Large deck with BBQ. Fully equipped kitchen. Wi-fi internet and premium channels cable tv. Pool table, basketball and children play ground for entertainment. Five min...
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    Location Information
    11946, Hampton Bays, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • 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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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    Mini Resort in East Hampton on a private acre1 / 22
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • DVD Player
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculate NW Woods Ralph Lauren furnished modern contemporary home has it all including a Hot Springs Spa, custom Heated Pool with stand alone Pool House, 3000 sq. ft. of decking that wraps around entire back of home leading down to the pool area with all the outdoor furniture/seating you...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sag Harbor with water views & perfect sunsets1 / 11
    (8)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Air Conditioning
    • Patio
    • Porch
    • Ocean Views
    • Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We felt very fortunate to have found this property! We have dear friends nearby who were hosting a birthday celebration and their house was full... our rooms were lovely and we...
    Reviewed 13 July 2017
    Combine a shore-front location with a welcoming inn-keeping couple, a historic house lovingly maintained and furnished in period comfort, and you get Payne House--a...
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    About this property
    This whaling captain's house has been in my family six generations. We offer the original wing of house for weekend rental May through October. One bedroom has a water view, the second bedroom is larger at the front of the house, and they share a dressing room/office. The room at the front of...
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    Location Information
    11963, Sag Harbor, Hamptons
    Private Room - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beautiful Southampton home with large pool  jacuzzi sleeps 13 Beach & Town1 / 28
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Internet Access
    • Hot Tub
    • Washer
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    Great location and close to town. Pool and Jacuzzi are beautiful. Would definitely recommend to anyone looking for a nice weekend out east.
    Reviewed 8 July 2017
    Recently spent a week in the Shinnecock Hills home. It way exceeded my expectations. The house is a perfect setup and size for a large shared group or family. There is plenty of...
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    About this property
    Beautiful Southampton home. Very private with a large pool and a beautiful, large Jacuzzi. This home is perfectly located in Southampton. Sleeps 13. If you have been wanting to visit The Hampton's for the first time house is the perfect choice since its perfectly located in the heart of the...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    The Graybarn Cottage in the Heart of East Hampton1 / 123
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In a quaint seaside village of historic beach homes The Graybarn Cottage is like no other. For 15 years The Mill House Inn has defined luxury accommodations in the Hamptons. Now we cordially invite you to relish in the luxury of a very special home, one designed exclusively with our clients'...
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    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Exquisite Waterfront Estate on Shelter Island NY; 100 Foot Dock; Beaches, Town1 / 14
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Reviewed 22 September 2016
    This house was fantastic. It felt more like a home than a rental house. The garden is massive and runs down to the water with a jetty. The kitchen is really well equipped and...
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    About this property
    Beautifully renovated waterfront cottage from early 1800s. Marble baths, two master suites. Sweeping waterfront lawn. 100 foot dock. Swimming, boating, grill on back deck. Beaches easy bike ride or walk. All amenities. Flat screen TVs in all bedrooms, wood burning fireplace. Restaurants, bars,...
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    11964, Shelter Island, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    This cozy furnished country-style farmhouse sleeps ten people comfortably and is minutes to ocean or bay beaches, shopping, and restaurants. The house sits on over an acre of land adjacent to 1,000-acre Long Pond Reserve. Out back is a wooden deck, an in-ground pool, and a pool house. There are 8...
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    11932, Bridgehampton, Hamptons
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    >>> ROMANTIC Beach Getaway! Seclusion, Waterfalls1 / 20
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
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    • Internet Access
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your...
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    Location Information
    11964, Shelter Island, Hamptons
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located down a winding drive in the town of East Hampton our four bedroom home was constructed in the classic Hampton's style with cedar shingles and white wood trim. Sited on an acre and a half in the Northwest Woods, beautifully landscaped and private with close to 20 acres of reserve land...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Outdoor Dining Area
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walking distance to harbor. 10 minutes north to bay beaches, 10 south to downtown East Hampton and ocean beaches. Upside down house with master bedroom and bath, 25x15 room with grand piano and kitchen upstairs, deck; 3 bedrooms and 2 baths downstairs. Light and airy!
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Grill
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is nestled in a park like setting with a private tree-lined yard. You will have all the privacy you want. Enjoy a beautiful built in pool & Jacuzzi. The home is clean, stylishly decorated, and steps away from a gorgeous north Sea bay beach. Visit Southampton or Sag Harbor town only 3 min...
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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 7 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to your private Hamptons escape! Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this immaculate Southampton vacation rental house is sure to provide the perfect spot for families or a close group of friends traveling together. Boasting a beautiful...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is right on the sand, just a block away from a beautiful, uncrowded ocean beach in one of the world's most famous resort communities. Clean and comfortable, there is an upstairs deck off the living room and a downstairs patio off the eat-in kitchen, three bedrooms, two full bathrooms, a...
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    Location Information
    11930, Amagansett, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lauren Berger Collection : Westhampton House!! Dating back to 1890, this historic home exudes vintage charm as well as providing all the contemporary conveniences required for a memorable wedding day or family gathering. Noteworthy original features include vaulted ceilings, wide plank oak...
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    Location Information
    11977, Westhampton, Hamptons
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in Montauk, but hide from the club scene at our clean and roomy beachhouse Our spacious and modern condo townhouse on the golf course is perfect for one or two families to share. There are two master suites, and a kids room with 5 beds. 2 full bathrooms and one half, ensure there is never a...
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    Location Information
    11954, Montauk, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Tranquil Montauk House Near Ocean, Bay, Sports1 / 13
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4BR House Minutes From Ocean & Across From Montauk Downs (golf, Tennis, Pool) This newly listed and furnished 4 bedroom, 2 bathroom beach house in Montauk is ready for August through Labor Day weekend. Also available in September. The property is across from Montauk Downs - public tennis, golf,...
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    11954, Montauk, Hamptons
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3500 sq ft Hampton's styled home has a large light filled living room with fireplace and sliding glass doors to the expansive deck with heated pool. The open floor plan makes this home perfect for entertaining. This home is situated on .75 of an acre of property that backs up to a private...
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    Location Information
    11976, Water Mill, Hamptons
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Washer
    • Private Outdoor Pool (Heated)
    • Grill
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RR#16-992 4/09/2018 Heading to the Hamptons? Then go ahead and book this 6-bedroom, 5.5-bathroom vacation rental home in Amagansett with sleeping for 12! Great for larger families, friends, or couples seeking a beach getaway, this will serve as the perfect home base for all of your adventures....
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    Location Information
    11930, Amagansett, Hamptons
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Sag Harbor designer home, Chef's kitchen & one block from the water1 / 14
    (2)Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We loved everything about this place. From the outdoor fire pit to my elderly parents having the time of their lives. Everything was impeccable. We look forward to returning...
    Reviewed 23 March 2017
    Our family enjoyed a great week in Sag Harbor and wonderful accommodations. The house is as advertised, nicely and warmly decorated with beautiful pool and outdoor grounds. The...
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    About this property
    For a truly authentic experience of Sag Harbor, stay at this delightful 5-bedroom, 2-bathroom designer's home with oversized heated pool and ideally situated just 2 blocks from Long Beach . With 2,800-square feet of living space and enough sleeping accommodations for up to 10 guests, this residence...
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    Location Information
    11963, Sag Harbor, Hamptons
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Hampton accommodations  21 / 8
    (3)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Satellite TV
    • Grill
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    • DVD Player
    • Central Heating
    • Secure Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2015
    Cori's a lovely hostess and her place is immaculate. The outside shower rocks and the deck is super relaxing . She's well versed in all that the east end has to offer from the...
    Reviewed 16 September 2014
    Great choice for a stay in the East Hampton Area!Clean Comfortable room with queen size bed that will give you a good nite sleep!Italan tiled full bath also clean and...
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    About this property
    Cozy -Clean- sunny Queen Size Bed - AC. Cable Tv with Premium Channels- WiFi Full bath - Half Bath - OutDoor Shower. Complimentary Breakfast Each Morning / Self-Serve Coffee Free In-House Bicycles for your enjoyment. One Mile to Beach - Ten Min to East Hampton Village Close to Great Harbor Front...
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    Location Information
    11937, East Hampton, Hamptons
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Sag Harbor with perfect water view and sunset1 / 14
    (3)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Outdoor Dining Area
    • Ocean Views
    • Secure Parking
    • Air Conditioning
    • Waterfront
    • Porch
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    My family have just spent 7 days at a charming whaling cottage in Sag Harbor.The position to town was great and the tranquility of the home was ideal.The owners Anne and Dave...
    Reviewed 8 July 2016
    Ann and Dave offer this lovely, historic home to guests and provide everything needed for a wonderful stay. The porch overlooking the water is heavenly. You really feel like...
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    About this property
    Historic whaling captains home. We are the sixth generation to live here. It is a quick walk from our house to the village of Sag Harbor, where you will find restaurants, boutiques, antique stores, marinas and much more. If you wish to stay around the house, we have a dock, hammock and the best...
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    Location Information
    11963, Sag Harbor, Hamptons
    Private Room - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    "Amazing Summer Getaway In East Quogue"1 / 28
    (3)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    This homey 8-bedroom house is on a beautiful, quiet street, just a short drive from wineries, the beach, great restaurants with ocean views, and the town of South Hampton. I...
    Reviewed 6 July 2016
    We stayed here for a long holiday weekend. The house had enough rooms to easily accommodate our entire family and local friends who visited us. The pool was great and well...
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    About this property
    Beautiful two level 4,100 sq. ft. home in East Quogue is sure to accommodate all your summer get away needs. If you enjoy spending quality time together our home provides a large backyard with an in-ground heated pool, and a new BBQ. Than come hang out inside in our game room that holds a...
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    Location Information
    11942, East Quogue, Hamptons
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning contemporary house is set on two private acres in the near Northwest Woods. Bright, white filled with sunlight, this four bedroom, two and a half bath multi-level home has soaring cathedral ceilings on the main level, large king master bedroom suite with private deck, TV, new bath...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Southampton, this 6 bedroom home is 8 km from Agawam Park. Southampton 6 Bed with Pool features a grand entrance, kitchen area with marble counters, stainless steel appliances and French doors with an outside seating area. The living room offers an archway with a fireplace and separate...
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    Location Information
    11968, Southampton, Hamptons
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    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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    Location Information
    11932, Bridgehampton, Hamptons
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Grill
    • Secure Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful four bedroom, two bathroom beach house is newly renovated and available for rent! Located on .7 acres, this property is a dream come true for all those looking for a peaceful escape into one of the most beautiful parts of the country. Our lovely home is located only 7 minutes away...
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    Location Information
    11937, East Hampton, Hamptons
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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