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Vacation Rentals and House Rentals in Shelter Island, NY

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    From
    $2,500
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    4 Bedrooms, 3 Bathrooms, Sleeps 6
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    From
    $2,100
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    3 Bedrooms, 2 Bathrooms, Sleeps 4
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    $1,400
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    6 Bedrooms, 7 Bathrooms, Sleeps 17
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    $5,000
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    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Washer
    • Dryer
    • Wi-Fi
    • Private Tennis Court
    • Private Outdoor...
    • Fireplace
    • Air Conditioning
    • Pool Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • 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
    From
    $2,500
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • TV
    • Watersports Nearby
    • Deck
    • There Are Tennis...
    • Dryer
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Lovely summer home on a quiet cul-de-sac. Renovated bathrooms and a fully-equipped renovated kitchen with a convection oven, dishwasher and more. Large, well-maintained 1/2 acre yard with private outdoor shower, two lovely open decks plus a screened dining porch with seating for 8. Three bedrooms... View all property information
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    Location Information
    Shelter Island, Hamptons 11964
    From
    $350
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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Satellite TV
    • Private Outdoor...
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    $350
    / Night
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    1 / 16
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Stereo System
    • Private Outdoor...
    • Fireplace
    • Deck
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Inquiry
    Location Information
    Shelter Island, Hamptons 11965
    From
    $400
    / Night
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    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Waterfront
    • Stereo System
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    From
    $325
    / Night
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Internet Access
    • Stereo System
    • Air Conditioning
    • Deck
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    $400
    / Night
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    1 / 30
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Reviews (1) Make Inquiry
    Overview Reviews (1)
    Amenities & Details
    • Hot Tub
    • Satellite TV
    • Stereo System
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Inquiry
    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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    From
    $325
    / Night
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
    Amenities & Details
    • Private Outdoor...
    • Fireplace
    • Satellite TV
    • Stereo System
    • Deck
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Make Inquiry
    Location Information
    Shelter Island, Hamptons 11965