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Vacation rentals in Shelter Island

Vacation rentals in Shelter Island

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shelter Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Beautiful Shelter Island getaway..Gourmet kitchen!
    Entire house · 6 guests · 4 beds · 3.5 baths
    Beautiful Shelter Island getaway..Gourmet kitchen!

    Perfectly situated just past the Island Boatyard and Salt in a peaceful neighborhood surrounded by water on 3 sides. 4 town landings and beach access across the street. Newly renovated gourmet kitchen with large island and beautiful marble counters. 3 bedrooms upstairs and private office off of master suite, a 4th bedroom on the first floor and finished basement with full bathroom. Use if two kayaks and paddle board make this the perfect getaway retreat!

    What guests are saying:

    “The house was spacious, stylish and clean and would be comfortable for a large group, though there were only 2 of us. The pool is beautiful and private. There are water views from the master bedroom upstairs. We enjoyed using the two kayaks — there are a couple entry points within carrying distance if you are fairly strong. Shelter Island is very low key and great for kayaking! There are also some good (and pricey) restaurants on the island. We also enjoyed exploring nearby Greenport, Sag Harbor and Montauk - easily reachable by ferry/car. Unfortunately, the weather was not on our side, otherwise we would have spent a day or two on Cresent/Sunset beach on the island. We did go to the Pridwin and catch an amazing sunset. Recommend!”

  • The Lord‘s Cottage on the Water
    SUPERHOSTEntire house · 4 guests · 3 beds · 2 baths
    The Lord‘s Cottage on the Water

    Cozy, quiet, newly renovated cottage on the picturesque Menantic Peninsula. Located on a Shelter Island historical landmark (The Lord's Shipyard), and perfect for families or couples looking for a quiet paradise nestled in nature on the sea. 5 minute walk from the Island Boatyard and excellent restaurants, and a 5 minute drive from Sunset Beach. Sea views from every room and bathroom. Stunning sunsets every evening visible from the back porch.

    What guests are saying:

    “My wife and I went out during the week in late August. The house is tucked away from the road, overlooking beautiful waterways with a really nice front lawn. Hosts are very friendly and accommodating (by airbnb/text message). Overall, we had everything we needed and really enjoyed our stay. We could hear the construction next door during the day, but weren't there much as we were exploring beaches, town, etc, and all was quiet by late afternoon for sunset on the water. Thanks for the hospitality. We'd certainly come back.”

  • Squire Chase House
    SUPERHOSTEntire apartment · 6 guests · 3 beds · 2 baths
    Squire Chase House

    Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

    What guests are saying:

    “Jason's apartment is exceptional. It is right in the heart of Shelter Island -- you can walk to many great restaurants and cafés nearby and go on beautiful run or walk in any direction. The apartment is SO spacious. It is situation on multiple levels with enormous common areas -- beautiful high-ceiling, sunny, and well-lit living room, kitchen, and dining area. There are three very thoughtfully appointed bedrooms, and the top floor has a master suite and an additional room that make give it added privacy from the main floor, complete with a huge bathroom. The kitchen is well stocked, and there are multiple outdoor spaces -- huge balconies, including one with a grill. The place is filled with beautiful coffee table books on art, cooking, and photography, board games, entertainment, etc. We had 3 couples stay in this apartment for a weekend and it couldn't have been more comfortable. Jason was so easy to communicate with, and check-in and check-out were a breeze given the keypad entry. Thank you!”

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Popular amenities for Shelter Island vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Shelter Island

Beautiful Shelter Island getaway..Gourmet kitchen!
Entire house
Beautiful Shelter Island getaway..Gourmet kitchen!
Price:$447 CAD/night
Squire Chase House
SUPERHOSTEntire apartment
Squire Chase House
Price:$482 CAD/night
The Lord‘s Cottage on the Water
SUPERHOSTEntire house
The Lord‘s Cottage on the Water
Price:$319 CAD/night
Case-Jennings House on Shelter Island    20-B-0001
SUPERHOSTEntire house
Case-Jennings House on Shelter Island 20-B-0001
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Shelter Island Year Round Luxury
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A room for 2 with a shared bath
Private room
A room for 2 with a shared bath
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Bridgehampton Private Loft Walk to Town Monthly
Tiny house
Bridgehampton Private Loft Walk to Town Monthly
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Shelter Island Lake House Retreat
Entire house
Shelter Island Lake House Retreat
Price:$688 CAD/night
Studio sweet on Shelter Island
SUPERHOSTEntire guest suite
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Price:$179 CAD/night
Relax on the North Fork in Orient!
Entire apartment
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Price:$117 CAD/night
Sleek and Chic cottage/Pool House
Entire guesthouse
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Escape! Immaculate NEW Beach Cottage Sleeps 2-4
SUPERHOSTEntire cottage
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Price:$812 CAD/night
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