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Holiday Rentals in Shelter Island, NY

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    All 8 Rentals in Shelter Island
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    From
    $521
    / Night
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    1 / 30
    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    $326
    / Night
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    1 / 11
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    From
    $1,824
    / Night
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    6 Bedrooms / 7 Bathrooms / Sleeps 17
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    $520
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    1 / 26
    4 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home: 4 bedrooms (we have two master bedrooms with their own porches), 2 baths, plus outdoor shower, large kitchen with double farmhouse sink and new GE washer/dryer, full dining room, large living room with large brick fireplace,... View all property information
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    Location Information
    Shelter Island, Hamptons 11965
    From
    $456
    / Night
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    1 / 16
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Enquiry
    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
    $2,997
    / Week
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    1 / 20
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large Shelter Island Farmhouse Beautiful Shelter Island is the most enjoyable, preserved, natural beauty on the North Fork and is yours to explore. Relaxing is mandatory... The farmhouse is close to all - steps from the golf course and beach 46 West Neck Road - overlooks Town Golf Course+ 1 Block... View all property information
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    Location Information
    Shelter Island, Hamptons 11965
    From
    $424
    / Night
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    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
    $6,515
    / Week
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    1 / 20
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    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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