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House Rentals and Apartments in Shelter Island, NY

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    Travelers to Shelter Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    1 / 35
    Private Room, 4 Bathrooms, Sleeps 11 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Large Shelter Island Farmhouse<BR>Beautiful Shelter Island is the most enjoyable, preserved, natural beauty on the North Fork and is yours to explore. Relaxing is mandatory...<BR>The farmhouse is close to all - steps from the golf course and beach<BR>46 West Neck Road - overlooks Town Golf Course+... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    About this property
    This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking distance to Silver Beach off of Bootleggers Alley. We have bikes on hand to help you reach these and other beautiful destinations around... View all property information
    Location Information
    Shelter Island, Hamptons 11964
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Outdoor Dining Area
    • Terrace
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    • Grill
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    • Balcony
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    About this property
    Tennis Court, Swimming Pool, Bocci, Soccer Lawn, Luxury Shelter Island 3-Bedroom<BR>Located in what is arguably the most desirable part of the island, this house appeals to guests who are looking for clean, modern, and stylish accomodations in a picturesque setting. Huge open kitchen with Sub-zero... View all property information
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    Shelter Island, Hamptons 11964
    1 / 19
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
    Location Information
    Shelter Island, Hamptons 11964
    1 / 30
    4 of 5 bubbles (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Waterfront
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    About this property
    DURING THE PEAK MONTHS, THIS HOUSE IS ONLY AVAILABLE BY THE WEEK OR LONGER! We just completed remodeling 2 of the baths and some additional painting. We just had custom plush white leather seating in the eat in kitchen nook as well as the window seat in one of the bedrooms. We are in the... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    4 of 5 bubbles Reviewed March 23, 2015
    My wife and I are very hard to please when it comes to travel and accommodation. However, Shelter Island Hideaway left us wanting more. The pergola, the décor, the pool, the semi...
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    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... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    1 / 17
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master with an attached private office, 2.5 baths, living, dining, entertaining spaces and... View all property information
    Location Information
    Shelter Island, Hamptons 11965
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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    • Private Outdoor...
    • Washer
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    This eclectic 'Round' house is a one of a kind on Shelter Island. Sited on 1.5 acres in Hay Beach with slices of bay views, this upside down house offers 4 Bedrooms and 2 Baths on the ground floor with an open layout upstairs which includes the living and dining room, kitchen, ½ bath, and covered... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    Shelter Island Flight and Weather Info
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    Additional Shelter Island Info

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