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Shelter Island Flight + Hotel packages

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See all 468 Properties in Shelter Island
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk
    4.0 out of 5.0
     
     

    Nestled on the beach, this Montauk resort is within 3 mi (5 km) of Hither Woods Preserve, Kirk Park Beach, and South Edison Beach. Napeague State Park and Second ...

    Gurney's Montauk Resort & Seawater Spa$264

    Gurney's Montauk Resort & Seawater Spa$264
    Water's Edge Resort & Spa

    Water's Edge Resort & Spa

    1525 Boston Post Road, Westbrook
      3.5 out of 5.0
       
       

      This Westbrook resort is on the beach, 1.7 mi (2.8 km) from Tanger Outlets, and within 6 mi (10 km) of Harvey's Beach and Indian River Marina. General William ...

      Water's Edge Resort & Spa $155

      Water's Edge Resort & Spa $155
      The Atlantic Hotel

      The Atlantic Hotel

      1655 County Road 39, Southampton
        2.5 out of 5.0
         
         

        Situated by the ocean, this hotel is 1 mi (1.7 km) from Shinnecock Hills Golf Course and within 3 mi (5 km) of Shinnecock Nation Cultural Center and Museum and ...

        The Atlantic Hotel$105

        The Atlantic Hotel$105
        Gurney's Montauk Yacht Club & Resort

        Gurney's Montauk Yacht Club & Resort

        32 Star Island Rd, Montauk
          3.5 out of 5.0
           
           

          Nestled on the beach, this Montauk hotel is within 2 mi (3 km) of Montauk Marine Basin, Montauk Downs State Park Golf Course, and Montauk Downs State Park. Fort ...

          Gurney's Montauk Yacht Club & Resort$250

          Gurney's Montauk Yacht Club & Resort$250
          Bayview Resort

          Bayview Resort

          53 West Tiana Road, Hampton Bays
            2.5 out of 5.0
             
             

            Situated by the ocean, this motel is within 6 mi (10 km) of Meschutt Beach, Ponquogue Beach, and Quogue Community Hall. Shinnecock Hills Golf Course and Shinnecock ...

            Bayview Resort$235

            Bayview Resort$235
            Saybrook Point Inn, Marina and Spa

            Saybrook Point Inn, Marina and Spa

            2 Bridge St, Old Saybrook
              3.5 out of 5.0
               
               

              Situated on the waterfront, this spa hotel is 1.5 mi (2.4 km) from General William Hart House and 1.7 mi (2.7 km) from Katharine Hepburn Cultural Arts Center. ...

              Saybrook Point Inn, Marina and Spa$229

              Saybrook Point Inn, Marina and Spa$229
              Montauk Manor

              Montauk Manor

              236 Edgemere St., Montauk
                3.5 out of 5.0
                 
                 

                Situated near the beach, this condo resort is within 2 mi (3 km) of Fort Pond Bay Beach, South Edison Beach, and Shadmoor State Park. Montauk Downs State Park ...

                Montauk Manor$136

                Montauk Manor$136
                Southampton Inn

                Southampton Inn

                91 Hill Street, Southampton
                  3.0 out of 5.0
                   
                   

                  This family-friendly Southampton hotel is located by the ocean, within a 5-minute walk of Agawam Park and Southampton Cultural Center. Southampton Historical ...

                  Super 8 by Wyndham Old Saybrook

                  Super 8 by Wyndham Old Saybrook

                  37 Spencer Plain Rd, Old Saybrook
                    2.0 out of 5.0
                     
                     

                    Situated in Old Saybrook, this hotel is within 3 mi (5 km) of Katharine Hepburn Cultural Arts Center, General William Hart House, and Harvey's Beach. Tanger ...

                    Super 8 by Wyndham Old Saybrook$59

                    Super 8 by Wyndham Old Saybrook$59
                    Kenny's Tipperary Inn

                    Kenny's Tipperary Inn

                    432 West Lake Drive, Montauk
                      2.0 out of 5.0
                       
                       

                      Situated near the airport, this motel is within a 10-minute walk of Montauk Marine Basin and Gin Beach. Montauk Downs State Park and Montauk Downs State Park ...

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