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Vacation Rentals and House Rentals in Shelter Island, NY

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    All 8 Rentals in Shelter Island
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    $2,300
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    3 Bedrooms / 2 Bathrooms / Sleeps 4
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    $399
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    4 Bedrooms / 3 Bathrooms / Sleeps 6
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    $1,400
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    6 Bedrooms / 7 Bathrooms / Sleeps 17
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Our Quaint two bedroom house offers easy access to everything on Shelter Island. Large backyard offers room to kick back or to run around. Bedrooms are comfortable. one with a queen size bed, another with two twins - for those kids of yours, or push them together for a king size bed for extra... View all property information
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    Location Information
    Shelter Island, Hamptons 11964
    4 of 5 stars Reviewed August 16, 2014
    This is a reasonably priced and clean place to stay. The furniture and furnishings are dated from the 60's/70's and it has a slightly musty feel. Other than that, it's a good deal...
    5 of 5 stars Reviewed August 5, 2013
    Everything about this rental was outstanding. The space is clean, airy, as shown in the photos. The yard is large and very beautiful, and the place is peaceful. The location is...
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    $400
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    1 / 30
    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    Shelter Island, Hamptons 11965
    4 of 5 stars Reviewed March 24, 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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    $350
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    1 / 16
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Shelter Island, Hamptons 11965
    From
    $325
    / Night
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • 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
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    Location Information
    Shelter Island, Hamptons 11965
    From
    $5,000
    / Week
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Pool Table
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Tennis Court, Swimming Pool, Bocci, Soccer Lawn, Luxury Shelter Island 3-Bedroom 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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    Location Information
    Shelter Island, Hamptons 11964
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