Skip to content
Sign up
Log in
Vacation rentals in Shelter Island

Vacation rentals in Shelter Island

Find and book unique accommodation on Airbnb

Top-rated holiday 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 bathrooms
    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!”

  • Roomy Hamptons Apartment - Pet friendly!
    SUPERHOSTEntire flat · 2 guests · 1 bed · 1 bathroom
    Roomy Hamptons Apartment - Pet friendly!

    Separate entrance lower level apartment surrounded by woods on a quiet cul de sac in a private neighborhood. House trained pets welcome! Queen size bed, Full package Cable TV, Netflix, WiFi, AC, board games. Unheated pool and BBQ in summer.

    What guests are saying:

    “I enjoy staying 2bed rooms apartment. It was very clean and amenities are awesome!! Will come back soon in the summer time. I had a very good time during my stay.”

  • Squire Chase House
    SUPERHOSTEntire flat · 6 guests · 3 beds · 2 bathrooms
    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!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Shelter Island holiday rentals

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

Other great holiday rentals in Shelter Island

A room for 2 with a shared bath
Private room
A room for 2 with a shared bath
Price:£104 / night
Beautiful Shelter Island getaway..Gourmet kitchen!
Entire house
Beautiful Shelter Island getaway..Gourmet kitchen!
Price:£263 / night
Squire Chase House
SUPERHOSTEntire flat
Squire Chase House
Price:£283 / night
Barons Cove- Harbor 2 Queen Room
SUPERHOSTEntire flat
Barons Cove- Harbor 2 Queen Room
Price:£202 / night
Case-Jennings House on Shelter Island    20-B-0001
SUPERHOSTEntire house
Case-Jennings House on Shelter Island 20-B-0001
Price:£211 / night
Studio sweet on Shelter Island
SUPERHOSTEntire guest suite
Studio sweet on Shelter Island
Price:£105 / night
Quiet and cozy apartment in the heart of Greenport
SUPERHOSTEntire flat
Quiet and cozy apartment in the heart of Greenport
Price:£154 / night
The Lord‘s Cottage on the Water
SUPERHOSTEntire house
The Lord‘s Cottage on the Water
Price:£188 / night
Refined Cottage on Idyllic Shelter Island
Entire house
Refined Cottage on Idyllic Shelter Island
Price:£283 / night
Greenport Pied A Terre
SUPERHOSTEntire flat
Greenport Pied A Terre
Price:£117 / night
American Beech - Deluxe King 6
SUPERHOSTRoom in boutique hotel
American Beech - Deluxe King 6
Price:£177 / night
Greenport Village Retreat. Walk to it All - Apt #2
SUPERHOSTEntire house
Greenport Village Retreat. Walk to it All - Apt #2
Price:£121 / night
Show all