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Vacation Rentals near Shelter Island Craft Brewery

55 N Ferry Road, Near Jaspa Rd, Shelter Island, New York
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    Don't let other travelers get your favorite Shelter Island vacation rental. You're so close to securing your perfect getaway. Book today.
    All 45 Rentals in Shelter Island
    Waterfront Condo C204 at The Cliffside Resort1 / 14
    (11)Excellent
    3.3 miles from Shelter Island Craft Brewery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Victorian Seasons one bedroom duplex farmhouse1 / 28
    (4)Excellent
    3.8 miles from Shelter Island Craft Brewery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    North Fork House with Private Beach Access1 / 14
    (6)Excellent
    4.2 miles from Shelter Island Craft Brewery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Beautiful French Country Cottage1 / 23
    (4)Excellent
    3.7 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Wi-Fi
    • Patio
    • DVD Player
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    • Parking
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    If you love the North Fork you will absolutely love staying here. This cottage embodies everything that I wanted for my time spent here which happened to also be my birthday...
    Reviewed March 13, 2018
    My family of four stayed in one of these twin cottages. They are mirror images of each other with separate entrances and patios. Plenty of parking right outside and just...
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    About this property
    Welcome to the Victorian Seasons guest cottages, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful North Fork of Long Island....
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    East Marion, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    CHARMING ONE-BEDROOM EFFICIENCY APARTMENT IN THE HEART OF EAST MARION1 / 21
    (1)Excellent
    3.9 miles from Shelter Island Craft Brewery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed September 5, 2017
    Irene and her husband are personable, responsive to any requests and delightful to deal with. Irene saw to it that all our needs were attended to. All i did is ask whether...
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    About this property
    This is a one-bedroom efficiency apartment with a kitchen and bistro dining area, located in the heart of East Marion on the beautiful North Fork. It is part of the main farmhouse that dates to the late 1800's with a separate entrance that once belonged to the Stars family. Mr. Stars owned the...
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    East Marion, North Fork
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    WATERFRONT Estate on Shelter Island. Fully Renovated. 100 Ft DOCK1 / 30
    (2)Excellent
    1.0 miles from Shelter Island Craft Brewery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed October 25, 2017
    Real nice inside and out. Great views. Fishing off private dock. Crabs too, better in summer. Quiet, peaceful. Can cook indoors or out. Good for families.
    Reviewed September 21, 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
    WINTER SPECIAL: Stay for long weekend or Week for $999, plus utils, taxes. Any week, except holidays. 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...
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    Shelter Island, Hamptons
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Unique  English Country Cottage1 / 22
    (2)Excellent
    3.8 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Very cute, clean, neat, comfortable cottage in a peaceful setting with beautifully manicured surroundings. Definitely coming back again!
    Reviewed August 12, 2016
    The house was beautifully maintained inside and out with a fantastic outdoor area to sit chill and enjoy barbecues and watch the local wildlife with a pretty rocky road beach a...
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    About this property
    . North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air...
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    East Marion, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beach House In Wine Country; walk to beach, large sun room, outdoor dining1 / 16
    (2)Excellent
    3.6 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
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    • Porch
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 3, 2015
    An absolutely stunning and beautiful home. Clean, comfortable, fully updated, this house is perfect for peace and relaxation. The bright and spacious sun room is perfect for...
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    About this property
    Walk to our private beach just houses away, kick back with a local bottle of pinot in our beautiful sunroom, barbecue in the backyard or cook your favorites in our new kitchen and dine al fresco on the patio, dining room or eat at the counter and entertain the cook. We provide 2 comfortable...
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    Southold, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Relaxed Village Farmhouse1 / 17
    (1)Excellent
    3.0 miles from Shelter Island Craft Brewery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 11, 2018
    Beautiful home in a great location. Very comfortable bedding and areas to relax. The backyard feels like you've been transported to Italy as you sip wine under the grapes...
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    About this property
    1903 Village Farmhouse, full of character, light and air. A place to relax, unwind and drink wine on the front porch, say hello to our neighbors or take an afternoon nap. Walk into the village for shopping and dinner or ride your bike to the beach. Visit one of the many local wineries and stop...
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    Greenport, North Fork
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant Designer Hamptons Retreat in Sag Harbor1 / 28
    (5)Excellent
    3.2 miles from Shelter Island Craft Brewery
    5 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Patio
    • Private Outdoor Pool (Heated)
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    • DVD Player
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    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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    Sag Harbor, Hamptons
    Rental Home - 5 Bedrooms, 7 Bathrooms, Sleeps 12
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    2.6 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Original details abound. Large, bright & airy rooms. Brand new furnishings. Perfect for entertaining or a quiet weekend retreat. The Space Located on a tree lined street this...
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    Greenport, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Victorian Seasons Stirling1 / 44
    (5)Excellent
    3.0 miles from Shelter Island Craft Brewery
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 10, 2018
    I stayed here with two families for a weekend getaway and our jaws dropped when we saw this stunning property. Walking through the door felt like stepping back in time into the...
    Reviewed July 5, 2018
    Amazing stay at Victorian seasons and beautiful hospitality walking distance to Greenport village .. The grounds were breathtaking surrounded by beautiful gardens and amazing...
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    About this property
    Elegant and especially designed and built for one of the wealthiest bankers on the North Fork. Situated on enormous property in the most prestigious setting of the National Historic District in Greenport Village. Lovingly restored to its original elegance and authentic Classic Queen Anne...
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    Greenport, North Fork
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.9 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southold, NY Beach Cottage, Walk to Beautiful Founders Landing Beach, Farm Stands, Wine, Shopping, Let us know your dates! BI - Weekly Rental - Bring the Dog(s) & Work Here! WIFI & CABLE Beautiful Restful Retreat! Come experience award-winning wineries, antique shops, art galleries, Summer 2017...
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    Southold, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Farmhouse1 / 15
    (1)Very good
    2.4 miles from Shelter Island Craft Brewery
    5 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed February 6, 2017
    My family rented this house for the holiday week between Christmas and New Years. The house is located within walking distance to town - which was quite great The house has...
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    About this property
    Renovated and tastefully furnished, The Farmhouse features one of the largest wrap around porches in the village and it is enviably located steps away from the town's best restaurants and bars, as well as just 3 short blocks to the beach. The space Just steps away from the center of the Greenport...
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    Greenport, North Fork
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 14
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    2.8 miles from Shelter Island Craft Brewery
    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Private Yard
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    Pet friendly
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    Smoking allowed
    About this property
    You will love this 4 bedroom 4.5 bathroom charmer on a quiet street. Walk to town, shops, carousel LIRR Jitney and ferry to Shelter Island Golf course and beaches 1 mile away. There are over 40 wineries nearby. The front deck has 2 Adirondack chairs to just relax. A full deck off the back over...
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    Greenport, North Fork
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 9
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    0.5 miles from Shelter Island Craft Brewery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, Salt Restaurant, Sylvestor Manor, Gardeners Bay country club, Shelter Island Heights, and the...
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    Shelter Island Heights, Shelter Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.7 miles from Shelter Island Craft Brewery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Patio
    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and handicapped accessible throughout with wrap around deck, extra wide doorways, new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque...
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    Southold, North Fork
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.8 miles from Shelter Island Craft Brewery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Historic Greenport Village has been recently renovated and is in walking distance to all. This is a 2 family home that can be rented separately or together. Pricing here is for house 2. One bedroom has a queen and the other can be configured as a king or two twins. Parking, beach access, convenient...
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    Greenport, North Fork
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1.0 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a great summer retreat? Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. This renovated Country Cape is nestled on a spacious and lush ¾ acre wooded lot....
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    Shelter Island, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.7 miles from Shelter Island Craft Brewery
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Southold, North Fork
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4.2 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning, spacious three bedroom home, with water views from every room, and a heated gunite pool, will be your dream-come-true vacation rental. You will be minutes away from several gorgeous beaches as well as 1 mile from the lively and historic village of Sag Harbor. Decorated to a high...
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    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.0 miles from Shelter Island Craft Brewery
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Greenport, North Fork
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2.4 miles from Shelter Island Craft Brewery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Designed and built in 2003, this cozy house has water views of Peconic Bay, enormous glass skylights, fully equipped kitchen, two bedroom, two bath, washer, dryer, Wifi, flat screen tv, private rose garden, private parking, a kayak, two bicycles, public swimming dock at end of block, and is one...
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    Greenport, North Fork
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3.7 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peaceful Year-Round Escape in the Middle of Wine Country It's starting to warm up so come to the North Fork - Sip local wine on the front porch or watch the waves at the private beach which is just a short walk away. Relax and kick back in our 3 bedroom house in Long Island's North Fork. Close...
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    Southold, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.1 miles from Shelter Island Craft Brewery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    3 Bedrooms 3 Bathroom home for rent. Beautiful landscape and privacy on a full acre with gigantic fenced in backyard with playground. 5 minute walk or 1 minute drive to private community Peconic Bay beach. Excellent condition and comfort. Weber Grill, sun filled deck , quality entertainment system....
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    Southold, North Fork
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Five Bedroom Italianate Great House - The Gem of East Marion1 / 39
    (3)Excellent
    3.8 miles from Shelter Island Craft Brewery
    5 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Reviewed July 9, 2018
    We spent a long weekend at this beautifully restored property and the combination of location, expansive private land, and owners hospitality was unmatched. Like taking a walk...
    Reviewed July 5, 2018
    We stayed here with our infant son , my parents, my sister and her three kids and my other sister and her husband. There was plenty of room for all of us. Our nieces loved...
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    About this property
    Welcome to the Victorian Seasons Main House, nestled between wildlife preserves and protected land. Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful North Fork of Long Island. This...
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    East Marion, North Fork
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 9
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    Shorecrest Beach House, 4 bedroom private beach front, new renovation1 / 32
    (3)Excellent
    4.0 miles from Shelter Island Craft Brewery
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Waterfront
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    We were absolutely blown away by how lovely our stay was at this beach front cottage right on the water in Southold! From the gorgeous sunsets seen from the porch over the water...
    Reviewed July 24, 2018
    This beach house is located right on the north shore of the long island sound, perfectly placed in the middle of the North Fork close to all the beautiful wineries and breweries...
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    About this property
    Newly renovated with two new full bathrooms, new kitchen and second floor bedroom/family room with glorious views overlooking the Long Island Sound, the Shorecrest Beach House has never looked so good! The Shorecrest beach house is located on a grassy bluff overlooking the ocean and available for...
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    Southold, North Fork
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Victorian Seasons 1 bedroom Carriage House Duplex1 / 21
    (1)Excellent
    3.8 miles from Shelter Island Craft Brewery
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Pet friendly
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    Reviewed July 5, 2018
    Great hospitality and amazing place to relax and unwind . The landscaping Grounds were beautiful highly recommended
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    About this property
    Welcome to the Victorian Seasons One bedroom Carriage House Duplex. Nestled between wildlife preserves and protected land, Victorian Seasons is a significantly important historic site that dates back to 1855. It is on the historic corridor in the heart of East Marion on the beautiful North Fork of...
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    East Marion, North Fork
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4.2 miles from Shelter Island Craft Brewery
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Ocean Views
    • Porch
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this idyllic beachfront located directly on the Sound in Southold NY, only 1 hour 45 minutes from NYC. Open-air, camp-style rooms are part of the house's simple charm. Linger over meals with family and friends on the screened-in porch, watch mesmerizing sunsets, swim in the salt water,...
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    Location Information
    Southold, North Fork
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Victorian Seasons Cape1 / 34
    (1)Excellent
    3.8 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Yard
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2018
    Had an Amazing stay .lovely grounds . Fell in love with the Gazebo and great hospitality. Very accommodating staff . Highly recommend.. enjoyably stay - Walking distance to a...
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    About this property
    This is a newly renovated 3 bedroom cottage in the beautiful historic district of East Marion. Two new full bathrooms, beautiful full kitchen & dining room, den & living room. Bedroom #1 has 1 queen bed, bedroom #2 has 1 queen and bedroom #3 has 1 twin. Located close to beaches, ferry, Jitney...
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    Location Information
    East Marion, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    4.7 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Renovated Waterfront Cottage with private beach and spectacular views! The house sits on the edge of the bluff with views of a secluded cove on the sound and has access to an infinity deck where you can relax and enjoy the water views, the sunsets, the landscaped garden and the birdlife all around...
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    Location Information
    East Marion, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.3 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Central Heating
    • Grill
    • DVD Player
    • Washer
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique, romantic beach cottage on the water 11 steps from actual water. Mini waves crash, ocean breezes, amazing water and sunrise views. Windows galore. Experience one of the most memorable getaways you will never forget. Cozy, romantic immaculate new beach cottage, just finished and slept in...
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    Location Information
    Noyack, Hamptons
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3.2 miles from Shelter Island Craft Brewery
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Cable/satellite TV
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your dream vacation awaits at this beautiful English manor on over an acre of private estate, just a two-minute walk from the beach overlooking the bay. Sag Harbor Luxury Estate is the ideal home for your next Hamptons holiday. Come and unwind by the 40-foot heated pool or take a trip to the town...
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    Location Information
    Sag Harbor, Hamptons
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    3.8 miles from Shelter Island Craft Brewery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect Summer rental! 3 bed, 2.5 bath Cape Cod style home with partially finished basement. Backyard oasis with pool, grill and fire pit. Meticulously maintained and lots of sunlight. Open concept kitchen, dining and living room. Master bedroom with king bed and ensuite on first floor with...
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    Location Information
    Sag Harbor, Hamptons
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.2 miles from Shelter Island Craft Brewery
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
    • Central Heating
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat to this exquisite 5 BR Sag Harbor beach house. Perfect for getaways from NYC. This roomy 5BR 3 bath home is located on the quiet & exclusive North Haven Peninsula, with famous neighbors Matt Lauer & Jimmy Buffett. Enjoy the picturesque & serene Sag Harbor Village & just 5 minutes from...
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    Location Information
    Noyack, Hamptons
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    1.3 miles from Shelter Island Craft Brewery
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Grill
    • Hot Tub
    • Patio
    • Terrace
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    55 Shore is a spectacular waterfront villa on Shelter Island, just a short walk from Sunset Beach and its stylish hotel. Enjoying panoramic bay and sunset views and a private beach with two boat docks, the 7,500 square-foot villa features beautiful alfresco living areas, exquisite interior spaces,...
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    Location Information
    Shelter Island Heights, Shelter Island
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    3.9 miles from Shelter Island Craft Brewery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally built in the late 1800s this lovely house is in the center of our quaint town of East Marion. We are just two miles from Greenport, a bustling port town, where you can catch the Shelter Island Ferry or the last stop on the LIRR, and just 4 miles from Orient and the Cross-Sound Ferry to...
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    Location Information
    East Marion, North Fork
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2.8 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Wi-Fi
    • Patio
    • Parking
    • Grill
    • Children's Pool
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Greenport, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3.4 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated ranch private home with spacious deck, large teak dining set, new grill, CAC, washer/dryer, front porch, fully equipped kitchen, wall mounted flat screen TVs in every bedroom and family room, farm dining room table. Nicely appointed home within walking distance to gorgeous private...
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    Location Information
    Greenport, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3.1 miles from Shelter Island Craft Brewery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Greenport, North Fork
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.8 miles from Shelter Island Craft Brewery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is a water lover’s paradise on sheltered water with easy access to surrounding east end towns. “2 East” features over 1500 square feet of decks & porch on three levels overlooking West Neck Harbor, with an opportunity to be in sun or shade and still enjoy spectacular water views. There...
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    Location Information
    Shelter Island, Hamptons
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3.4 miles from Shelter Island Craft Brewery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Yard
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Guests are sure to enjoy a memorable vacation in this Pristine 3 bedroom/2 bath contemporary property in a quiet bay front community located steps away from a private beach facing Shelter Island and across from a well known North Fork vineyard. This property is located on a quiet dead end street...
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    Location Information
    Southold, North Fork
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1.8 miles from Shelter Island Craft Brewery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Terrace
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer Caribbean-style elegance....
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    Location Information
    Shelter Island Heights, Shelter Island
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.1 miles from Shelter Island Craft Brewery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On your next visit to the Hamptons area, be sure to secure this updated and relaxing retreat in the heart of East Marion. This classic Cape Cod 3-bedroom, 2.5-bathroom vacation rental home accommodates up to 8 travelers, and sits within walking distance to a secluded beach and community park with...
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    Location Information
    East Marion, North Fork
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.8 miles from Shelter Island Craft Brewery
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect Hampton's retreat awaits at 'Shelter Island Hideaway,' a beautiful 4-bedroom, 4-bathroom vacation rental home. The private estate has 3,000 square feet of indoor space and luxurious accommodations for up to 9-10 guests. Enjoy the spacious pool, lounge around in the 1,500 square feet of...
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    Location Information
    Shelter Island, Hamptons
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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