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Vacation Rentals in Shelter Island, NY

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    Travellers to Shelter Island are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    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 / 30
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
    • Satellite TV
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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 stars Reviewed 23 March 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
    3 Bedrooms, 4 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
    Location Information
    Shelter Island, Hamptons 11964
    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 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Private Garden
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    • x
    About this property
    Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home: Rental includes: Two kayaks, Tennis Court, Shelter Island Heights Private Beach Club Use (private beach, picnic area, playground, showers, cabanas) for you and your family Details: 4 bedrooms (we have two master bedrooms... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    1 / 35
    Private Room, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    About Seven Newly renovated in 2014, SEVEN bed and breakfast offers a selection guest rooms for various combinations of guests, with king, queen, double queen and double twin rooms. Each guestroom includes air conditioning, a flat screen television, light seasonal goose down comforters, 100%... View all property information
    Location Information
    Shelter Island, Hamptons 11965
    1 / 10
    4 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Satellite TV
    • Private Outdoor...
    • Air Conditioning
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on Shelter Island, NY down a quiet lane within walking distance of Wades Beach and the Nature Conservancy's Mashomack preserve. This impeccably maintained hilltop traditional, reminiscent of a European country home, is situated on 2 acres. Entering the front foyer, your eye will be drawn... View all property information
    Location Information
    Shelter Island, Hamptons 11964
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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    • Private Outdoor...
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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