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Long Island Vacation Rentals

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    Travelers to Long Island are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 13
    Snyder Square
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 6
    Southampton
    2 Bedrooms, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 22
    5 of 5 bubbles (4) Excellent
    East Hampton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 12
    Montauk
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This Is a smartly furnished, relaxing house close to everything that beautiful Montauk has to offer. We just purchased the house In April 2015 and did an extensive renovation... new bathrooms, new floors, new A/C, painted, and new appliances. The house Is warm and relaxing and is drenched in... View all property information
    Location Information
    Montauk, Hamptons 11954
    1 / 13
    Sagaponack
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    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... View all property information
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    Sagaponack, Hamptons 11962
    1 / 22
    Southampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    About this property
    ONE-OF-A-KIND VILLA NESTLED ALONG THE SHORE OF THE GREAT PECONIC BAY, with 180 degree views. The newly renovated and newly furnished (indoor as well as out) with all white interior consists of an open kitchen, living and dining area which lead to french doors, opening out to the beachside stone... View all property information
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    Southampton, Hamptons 11968
    1 / 28
    Southampton
    4 Bedrooms, 5 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Welcome to your private Hamptons escape! This immaculate Southampton vacation rental house is sure to provide the perfect vacation spot for your next family getaway. Featuring 4 bedrooms, 5 bathrooms, and enough space to comfortably sleep up to 7 guests, this gorgeous home is a terrific size and... View all property information
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    Southampton, Hamptons 11968
    1 / 22
    East Hampton
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 16
    Greenport
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    • Children's Pool
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    • Central Heating
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    • ?
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    • x
    About this property
    Historic home in Greenport Village walking distance to restaurants, water, shopping etc..bike or short drive from vineyards. Large yard with outdoor patio with BBQ and outdoor shower. 2 family home with two separate duplex units that can be rented separately or together. Perfect for family... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 18
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This is your opportunity to experience summer living as many can only ask for. Enjoy this spectacular new home on the west end of Newtown La and away from the maddening crowds. The four bedrooms, 3 1/2 baths, gunite heated pool, spa and waterfall surround an indoor as well as an outdoor kitchen... View all property information
    Location Information
    East Hampton, Hamptons 11937
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    1 / 16
    Greenport
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    About this property
    Walking distance to Greenport Village, Sound and Bay Beaches! 1200 sq ft Victorian cottage perfect for a retreat from the heat. Large patio, new kitchen and bath! 1840s historic poet's house, perfect for couples, small family or single seeking reprieve from Manhattan. Original hardwood floors, 2... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 13
    East Hampton
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This lovely home includes a chefs kitchen, formal dining, spacious living area and 1st floor Master suite.There is also a finished lower level with a recreation room, gym, with an additional two bedrooms and a bathroom. Exterior includes two car garage, heated pool with water feature and spa. Just... View all property information
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    East Hampton, Hamptons 11937
    1 / 6
    Wainscott
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Enjoy this Charming Renovated Cottage with 2 Bedrooms, 1 Bath, Beamed Vaulted Ceilings and a Screened in Front Porch. A pretty kitchen is located in one end of the house that leads to the pool with waterfall. The Master bedroom is located on the first floor with a very large walk in closet. With... View all property information
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    Wainscott, Hamptons 11975
    1 / 21
    Southold
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 11
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Ocean Views
    • Patio
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    • Pet-friendly
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    • x
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    • x
    About this property
    Beautiful sunny home with south exposure. Large chefs kitchen. Spacious living room with flatscreen tv, baby grand piano and large french doors leading to a spacious deck. Four large bedrooms. Huge master bedroom with seating area and flatscreen tv. Large master bathroom with open air double shower... View all property information
    Location Information
    East Hampton, Hamptons 11942
    1 / 55
    5 of 5 bubbles (7) Excellent
    Southampton
    7 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    • x
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    • x
    About this property
    This is extravagant living at its best. Picture yourself enjoying expansive water views and majestic sunsets. The park like setting lends itself to an idyllic outdoor paradise. This home has 7 huge bedrooms and 5 palatial bathrooms. The house boasts a wide-open floor plan with soaring cathedral... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 7
    Amagansett
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Amagansett Beach House sits directly on the most beautiful beach in the world. The main floor has 3 Bedrooms with decks to beach, 2 Full Baths, and laundry room. Upstairs is the Gourmet Kitchen, Dining & Living Areas, complete with Flat screen TV. Stunning deck overlooks Atlantic Ocean. Includes... View all property information
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    Amagansett, Hamptons 11963
    1 / 6
    Remsenburg
    5 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • ?
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    19th Century house on 3 acres of gardens and fields. Traditional styling has been infused with modern touches and updates. Cook's professional kitchen, central air conditioning, jacuzzi, steam shower, heated swimming pool, internet and multi-room music system. Close to beach and recreation... View all property information
    Location Information
    Remsenburg, Long Island 11960
    1 / 21
    Fair Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    An ideal spot for a comfortable, peaceful beach vacation. Our charming, renovated cottage is located in Lonelyville, on Fire Island a short drive or train ride from New York City. If you've never visited Fire Island you're in for a treat. Close to the city yet a galaxy away. There are no private... View all property information
    Location Information
    Fair Harbor, Fire Island 11706
    1 / 19
    Shelter Island
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • x
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    • x
    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,... View all property information
    Location Information
    Shelter Island, Hamptons 11964
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    1 / 17
    Bridgehampton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
    1 / 8
    Sag Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    NEW CENTRAL AIR CONDITION WITH NEST THAT KEEPS HOUSE KOOL AT ALL TIME .PRICELESS!! All room have the own TV's. All Beds are memory form and super comfortable .house is very clean wit all new linens. 2 ned bathrooms.great home feeling in a family neighborhood. you can walk or walk into town main st... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 12
    Southampton
    4 Bedrooms, Sleeps 8 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
    About this property
    Southampton, Luxury 4 Bed 2 Bath home with pool, minutes to everything! New 25 x 50 Salt Generated Pool, no maintenance and much easier on the eyes! 3 Minutes to Private Beach! Free Parking, NO Beach Passes needed! This 4 bedroom, 2 bath home is nestled on 1.5 acres which abuts a 10 acre... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 7
    Southampton
    5 Bedrooms, 10 Bathrooms, Sleeps 16 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    You can rent this weekly, bi-weekly or full summer season. Summer 2015 weekly rentals start at $7000/week for any weeks in June, $8750/week for any weeks in July and $9200/week for any weeks in August. You can rent for as little as a week in the summer season or monthly or seasonal. In the... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 9
    Southampton
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This spacious 5 bedroom, 5.5 bath home provides an amazing living room with vaulted ceilings and 2 wood burning fireplaces. Expansive windows and French Doors overlook the landscaped grounds and heated gunite pool. Top-of-the-line appliances in the kitchen with granite countertops, desk, wine... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 25
    Hempstead
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
    About this property
    Plan your memorable escape to Long Island with this dazzling 4-bedroom, 2-bathroom Hempstead vacation rental house, which sleeps 9, rendering it perfect for large families or groups of close friends looking to escape the hustle and bustle of busy city life. Featuring state-of-the-art amenities, a... View all property information
    Location Information
    Hempstead, Long Island 11550
    1 / 16
    5 of 5 bubbles (1) Excellent
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Pet-friendly
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    • x
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    • ?
    About this property
    (East Hampton Rental Registry #16-335) 4 bedroom/2 Bath Single Level House with Central Air-Conditioning, located in the beautiful Clearwater Beach community. Rental includes electronic pass to private gated bay beach 2 minutes away. 7 minutes to East Hampton town and 9 minutes to ocean... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 10
    Sag Harbor
    1 Bedroom, 1 Bathroom, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Located in the quaint historic whaling Village of Sag Harbor, 12 minute walking distance to the center of town, with close proximity to the bay and ocean beaches. This European designer's home totals 5000 sq.ft., the lower level just shy of 1000, sq ft and is the designer's private lower level... View all property information
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    Sag Harbor, Hamptons 11963
    1 / 17
    East Hampton
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 24
    Southold
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • x
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    • x
    About this property
    Large beach front with 5 bedrooms (2 ensuite), 4 living rooms, 3.5 baths This is the perfect home for the extended family vacation, with not only 5 bedrooms, including 2 with ensuite bathrooms but 4 separate sitting/family/den or game rooms plus a pool room! The unique layout offers areas to gather... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 15
    East Quogue
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
    About this property
    Light, Bright And Completely Renovated. Spacious Modern Contemporary Home. Offers 5 Bedrooms, 3.5 Baths On Over 2 Private Acres. Enjoy Heated Pool, Hot Tub And Tennis, Foosball And Ping Pong. Great Room W/Fireplace And Wall Of French Doors. Open To Expansive Poolside Deck Inviting Outdoor... View all property information
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    East Quogue, Hamptons 11942
    1 / 33
    Valley Stream
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Gorgeous Freshly remodeled 2 bedrooms/living room 1st floor Park View apartment. It comes with a Full bath (shower/tub combo) and a fully equipped kitchen (stove, fridge, microwave, toaster oven, pots/pans, dishware, glassware, silverware, and kitchen utensils). Its warm cozy feeling will make you... View all property information
    Location Information
    Valley Stream, Long Island 11580
    1 / 12
    4.5 of 5 bubbles (24) Very good
    Greenport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer... View all property information
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    Greenport, North Fork 11944
    1 / 12
    East Setauket
    5 Bedrooms, 8 Bathrooms, Sleeps 10 | Quick View
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    • x
    About this property
    A wonderful summer getaway with stunning waterfront views, a few steps away from private beach access. This house sits on 2 full acres of land with steps leading down to the beach great for getting jet skiing, getting a tan or fishing, secluded from the busy streets of Long Island. Including a full... View all property information
    Location Information
    East Setauket, Long Island 11733
    1 / 34
    Hampton Bays
    8 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    • ?
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    • x
    About this property
    Inspired by Walden, Thoreau and Emerson, Shell House is the quintessential luxury rental in the Hamptons. Dock in the nearby marina or rent a boat for the day. Shell House is your gateway to world class fishing, sprawling vineyards and quaint villages bustling with charming shops. With a resort... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 16
    Baiting Hollow
    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    About this property
    Seasonal rental within a 5 minute walk to private beach, ten minute walk to Giorgio's. 5 minute drive to local horse riding farm and ten minutes drive to local north fork wineries. 10 minute drive to downtown Riverhead, Long Island rail road, outlets and restaurants.... View all property information
    Location Information
    Baiting Hollow, Long Island 11933
    1 / 13
    Mattituck
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • x
    • ?
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    • x
    About this property
    The Space The New York TImes Real Estate Section on Sunday, Feb. 9th, 2014, talked about the multi-million dollar homes being built in the Hamptons. The article said, "The look of the homes is evolving: modern is making a comeback, but modern in the guise of barnlike. 'The modern barn is the... View all property information
    Location Information
    Mattituck, North Fork 11952
    1 / 13
    Greenport
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Entirely renovated, spacious and quiet farmhouse two blocks from the marina, and a 5 minute bike ride to the beach or town. With original hardwood floors, modern kitchen with Viking appliances, two fireplaces, grill, and al fresco dining under a pergola. Located in Greenport, NY, the middle of wine... View all property information
    Location Information
    Greenport, North Fork 11944
    1 / 5
    5 of 5 bubbles (2) Excellent
    Southold
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This Home is located minutes from beautiful Long Island sound beaches, wineries, and historic Greenport village. Whether you enjoy the sun or antiquing everything is hereby. The house was built in 2009, having all modern conveniences but still holding the North Fork charm. The home has a central... View all property information
    Location Information
    Southold, North Fork 11971
    1 / 41
    5 of 5 bubbles (3) Excellent
    East Hampton
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • Pet-friendly
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    • x
    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... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 16
    East Hampton
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Deliciously close to the shimmering bay, is this very special 5 bedroom, 4 bath shingled traditional beautifully sited on a serene 1.8 acre well-landscaped parcel in the desirable Grace Estate area between East Hampton and Sag Harbor. A distinctive coffered ceiling foyer leads to the vaulted living... View all property information
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    East Hampton, Hamptons 11937
    1 / 9
    Ocean Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This home is located on Fire Island in the heart of Ocean Beach. Minutes to the Atlantic Ocean, the Great South Bay and Ocean Beach Restaurants and shops. This Spacious 4 Bedroom house has two good sized master bedrooms upstairs each with its own balcony and two additional bedrooms downstairs... View all property information
    Location Information
    Ocean Beach, Fire Island 11770
    1 / 30
    5 of 5 bubbles (1) Excellent
    Hampton Bays
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other traveler has booked this property
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    For family or group adults over 28 years old please up to max.8 guests inquire with your specific details for availability I'm on several sites. Min.2 nights JUN or SEP, 3 nights JUL5-SEP4, 4 nights for JUL 4th week-end. EXTRA at check-in: refundable sec.deposit up to 48h via... View all property information
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    Hampton Bays, Hamptons 11946
    1 / 22
    Wading River
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beachfront vacation home rental available for July and August 2017. This 4 Bedroom/2 Bathroom Beach home has everything you need to make the most of summer. Located on a private beach with both inside and outside living areas ideal for summer. Each room offers priceless sound views, has luxury... View all property information
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    Wading River, Long Island 11792
    1 / 6
    Sag Harbor
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    This beach vibes cottage is located in Sag Harbor village, you can walk to town, bike or walk to the beach. The house is located in the only private beach community in Sag Harbor. The cottage comes fully furnished with everything you need to have a memorable stay in Sag Harbor. No smoking Not... View all property information
    Location Information
    Sag Harbor, Hamptons 11963
    1 / 15
    East Hampton
    4 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Satellite TV
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    AVAILABLE Summer and Beyond. Wonderful, delightful, story book style cottage with white picket fence for your vacation pleasure ! This adorable 4 bedroom home is fully renovated, charming shabby chic decor. There is a heated pool and large driveway. BRAND NEW OUTDOOR SHOWER for sun-watering your... View all property information
    Location Information
    East Hampton, Hamptons 11937
    1 / 13
    Southampton
    4 Bedrooms, 10 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
    • Balcony
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Getaway to this charming Cottage on the water with spectacular views!! 3 Bedrooms & Baths in the main house with a separate<BR>guest cottage with Bedroom, Kitchen & Bathroom. Heated water front Gunite Pool, Hot Tub, Dock plus Kayaks & Bikes. Close to the village of Southampton, beaches and all the... View all property information
    Location Information
    Southampton, Hamptons 11968
    1 / 22
    Bridgehampton
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Bridgehampton, Hamptons 11932
    1 / 18
    Bellport
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Private Outdoor...
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This house has it all! 3 bedrooms with plenty of space for addition guests to sleep in the den. 2 bathrooms. Big living room, dining room, eat in kitchen. The den boasts a large screen TV with surround sound. Patio with furniture and gas grill. Heated pool! Dish washer in kitchen. Washing machine,... View all property information
    Location Information
    Bellport, Long Island 11951
    1 / 3
    East Hampton
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
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    • Washer
    • Satellite TV
    • DVD Player
    • Outdoor Dining Area
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Sunny very comfortable 3Br 2Ba with formal dining room, sitting on quiet tree lined residential street in the Springs (East Hampton), close to fine restaurants, private beach, marinas and sports. Minutes from shopping, arts, and local seasonal attractions. Great for entertaining weekend guests.... View all property information
    Location Information
    East Hampton, Hamptons 11937
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