Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 750,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.



Top Hotel Deals

See all 455 properties in Shelter Island Heights
The Pridwin Hotel C$334
The Pridwin Hotel

The Pridwin Hotel

81 Shore Road, Shelter Island Heights
     
    4.2
    of 5, from 18 reviews
    3.0 out of 5.0

    Nestled on the beach, this Shelter Island Heights hotel is within a 10-minute walk of Crescent Beach, Sunset Beach, and Shelter Island Tennis Club. Shell Beach and Shelter Island Country Club are also within 3 mi (5 km).

    The Chequit Inn C$356
    The Chequit Inn

    The Chequit Inn

    23 Grand Ave, Shelter Island Heights
       
      4.6
      of 5, from 93 reviews
      4.0 out of 5.0

      Situated by the ocean, this hotel is within 1 mi (2 km) of Shelter Island Country Club, Sunset Beach, and Crescent Beach. Sylvester Manor and East End Seaport Maritime Museum are also within 2 mi (3 km). Greenport Station is 21 minutes by foot.

      Shelter Island House C$358
      Shelter Island House

      Shelter Island House

      11 Stearns Point Rd, Shelter Island Heights
         
        4.2
        of 5, from 17 reviews
        3.5 out of 5.0

        Situated near the beach, this hotel is within a 10-minute walk of Sunset Beach and Shelter Island Country Club. Crescent Beach and Shelter Island Tennis Club are also within 1 mi (2 km).

        House on Chase Creek
        House on Chase Creek

        House on Chase Creek

        3 Locust Avenue, Shelter Island Heights
           
          4.7
          of 5, from 14 reviews
          2.5 out of 5.0

          Situated near the beach, this bed & breakfast is within 1 mi (2 km) of Shelter Island Country Club, Sunset Beach, and Crescent Beach. Sylvester Manor and East End Seaport Maritime Museum are also within 2 mi (3 km). Greenport Station is 26 minutes by foot.

          West Neck Guesthouse C$295
          West Neck Guesthouse

          West Neck Guesthouse

          31 W Neck Rd, Shelter Island Heights
             
            4.3
            of 5, from 6 reviews
            3.5 out of 5.0

            Situated in Shelter Island Heights, this bed & breakfast is within a 15-minute walk of Sunset Beach, Shelter Island Country Club, and Crescent Beach. Sylvester Manor and Shelter Island Tennis Club are also within 1 mi (2 km).

            SEVEN - Shelter Island Guest House C$467
            SEVEN - Shelter Island Guest House

            SEVEN - Shelter Island Guest House

            7 Stearns Point Road, Shelter Island Heights
               
              4.9
              of 5, from 46 reviews
              3.5 out of 5.0

              Situated by the ocean, this bed & breakfast is within a 10-minute walk of Sunset Beach, Shelter Island Country Club, and Crescent Beach. Shelter Island Tennis Club and Sylvester Manor are also within 1 mi (2 km).

              Dering Harbor Inn
              Dering Harbor Inn

              Dering Harbor Inn

              13 Winthrop Road, Shelter Island Heights
                 
                4.2
                of 5, from 5 reviews
                2.5 out of 5.0

                Situated on the waterfront, this condo resort is within 1 mi (2 km) of Shelter Island Country Club and Sylvester Manor. Sunset Beach and Shelter Island Whale's Tail are also within 2 mi (3 km).

                Shelter Island! Central Air! Walk TO Sunset Beach!
                Shelter Island! Central Air! Walk TO Sunset Beach!

                Shelter Island! Central Air! Walk TO Sunset Beach!

                , Shelter Island
                   
                  0.0 out of 5.0

                  Situated in Shelter Island Heights, this historic vacation home is within 1 mi (2 km) of Crescent Beach, Shelter Island Country Club, and Shelter Island Tennis Club. Sunset Beach and Sylvester Manor are also within 2 mi (3 km).

                  Top Flight + Hotel Deals

                  Top Deals On Flights

                  These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.