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Cheap Shelter Island Hotels

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway, Montauk, NY
    4.0 out of 5.0
     
     

    Located in Montauk, Gurney's Montauk Resort & Seawater Spa is within a 10-minute drive of Shadmoor State Park and Montauk County Park.

    $550

    Hero Beach Club

    Hero Beach Club

    626 Montauk Hwy, Montauk, NY
      4.0 out of 5.0
       
       

      When you stay at Hero Beach Club in Montauk, you'll be on the beach, within a 10-minute drive of Montauk Point Lighthouse and Montauk Point.

      $256

      The Chequit Inn

      The Chequit Inn

      23 Grand Ave, Shelter Island Heights, NY
        4.0 out of 5.0
         
         

        With a stay at The Chequit Inn in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sylvester ...

        $195

        Topping Rose House

        Topping Rose House

        One Bridgehampton - Sag Harbor Turnpike, Bridgehampton, NY
          4.5 out of 5.0
           
           

          With a stay at Topping Rose House in Bridgehampton, you'll be within a 15-minute drive of Cooper's Beach and Children's Museum of The East End.

          $795

          The Maidstone

          The Maidstone

          207 Main Street, East Hampton, NY
            4.0 out of 5.0
             
             

            With a stay at The Maidstone in East Hampton, you'll be a 3-minute walk from Home Sweet Home Museum and 6 minutes by foot from Guild Hall.

            $595

            The 1770 House Restaurant & Inn

            The 1770 House Restaurant & Inn

            143 Main Street, East Hampton, NY
              4.0 out of 5.0
               
               

              With a stay at The 1770 House Restaurant & Inn in East Hampton, you'll be by the ocean, just steps from Guild Hall and a 4-minute drive from LongHouse ...

              $550

              Marram

              Marram

              21 Oceanview Terrace, Montauk, NY
                4.0 out of 5.0
                 
                 

                Located in Montauk, Marram is by the ocean, within a 15-minute walk of South Edison Beach and Shadmoor State Park.

                $325

                East Hampton Art House Bed & Breakfast

                East Hampton Art House Bed & Breakfast

                9 Bon Pinck Way, East Hampton, NY
                  4.0 out of 5.0
                   
                   

                  With a stay at East Hampton Art House Bed & Breakfast in East Hampton (Clearwater Beach), you'll be within a 5-minute drive of Pollock-Krasner House and Study ...

                  $463

                  Jedediah Hawkins Inn

                  Jedediah Hawkins Inn

                  400 South Jamesport Avenue, Riverhead, NY
                    4.0 out of 5.0
                     
                     

                    With a stay at Jedediah Hawkins Inn in Riverhead, you'll be within a 10-minute drive of Martha Clara Vineyards and Harbes Family Farm.

                    $295

                    A Butler's Manor

                    A Butler's Manor

                    244 North Main Street, Southampton, NY
                      4.0 out of 5.0
                       
                       

                      Located in Southampton, A Butler's Manor is in a rural location, within a 5-minute drive of Southampton Historical Museum and Southampton Arts Center.

                      $395

                      White Fences Inn

                      White Fences Inn

                      371 Montauk Highway, Water Mill, NY
                        4.0 out of 5.0
                         
                         

                        With a stay at White Fences Inn in Water Mill, you'll be by the ocean, within a 10-minute drive of Cooper's Beach and Parrish Art Museum.

                        $499

                        Orient Inn

                        Orient Inn

                        25500 Main Road, Orient, NY
                          4.0 out of 5.0
                           
                           

                          When you stay at Orient Inn in Town of Southold Town, you'll be by the ocean, within a 5-minute drive of Oysterponds Historical Society and Truman's Beach.

                          $295

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                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.