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

Join Orbitz Rewards
Earn rewards and exclusive perks with Orbitz Rewards, just like that.

Get Insider Pricing
Save up to 50% on select hotels with Insider Prices—it’s easy.

Save on Packages
Up to $536 by booking Flight + Hotel together*

Shelter Island Flight + Hotel packages

Shelter Island Hotels

See all 276 Hotels in Shelter Island
Waterfront Home on Beautiful Shelter Island W/large Deep Water Dock

Waterfront Home on Beautiful Shelter Island W/large Deep Water Dock

, Shelter Island
     
     

    Situated in Shelter Island, this vacation home is close to Sunset Beach, Shelter Island Country Club, and Sylvester Manor. Also nearby are Havens House and Crescent ...

    Immaculate New Construction Summer Getaway Home on Shelter Is. With Heated Pool

    Immaculate New Construction Summer Getaway Home on Shelter Is. With Heated Pool

    , Shelter Island
       
       

      Situated in Shelter Island, this vacation home is close to Havens House, Sylvester Manor, and Shelter Island Whale's Tail. Also nearby are Wades Beach and Shelter ...

      Sole East Resort

      Sole East Resort

      90 Second House Rd, Montauk
        3.0 out of 5.0
         
         

        Situated in Montauk, this hotel is within a 15-minute walk of Second House Museum and Kirk Park Beach. Fort Pond Bay Beach and South Edison Beach are also within ...

        Sole East Resort$269

        Sole East Resort$269
        Water's Edge Resort & Spa

        Water's Edge Resort & Spa

        1525 Boston Post Road, Westbrook
          3.5 out of 5.0
           
           
          4.5 out of 5 (4 reviews)

          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 $179

          Water's Edge Resort & Spa $179
          The Atlantic Hotel

          The Atlantic Hotel

          1655 County Road 39, Southampton
            2.5 out of 5.0
             
             
            4.0 out of 5 (3 reviews)

            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$189

            The Atlantic Hotel$189
            Gurney's Montauk Resort & Seawater Spa

            Gurney's Montauk Resort & Seawater Spa

            290 Old Montauk Highway, Montauk
              4.0 out of 5.0
               
               
              4.5 out of 5 (8 reviews)

              Nestled on the beach, this Montauk resort is within 3 mi (5 km) of Hither Woods Preserve, Kirk Park Beach, and South Edison Beach. Second House Museum is 2.3 ...

              Gurney's Montauk Resort & Seawater Spa$490

              Gurney's Montauk Resort & Seawater Spa$490
              Hampton Maid Motel

              Hampton Maid Motel

              259 E Montauk Hwy, Southampton
                2.5 out of 5.0
                 
                 

                Situated near the beach in Hampton Bays, this motel is close to Meschutt Beach, Shinnecock Hills Golf Course and Shinnecock East County Park. Area attractions ...

                Hampton Maid Motel$215

                Hampton Maid Motel$215
                Aqualina Inn Montauk

                Aqualina Inn Montauk

                20 South Elmwood Avenue, Montauk
                  2.5 out of 5.0
                   
                   
                  4.7 out of 5 (3 reviews)

                  Located in the heart of Montauk, this motel is within a 10-minute walk of South Edison Beach and Kirk Park Beach. Second House Museum and Shadmoor State Park ...

                  Aqualina Inn Montauk$109

                  Aqualina Inn Montauk$109
                  The Hermitage

                  The Hermitage

                  2148 Montauk Highway, Amagansett
                    3.5 out of 5.0
                     
                     

                    This Amagansett condo building is on the beach, 1.6 mi (2.6 km) from Hither Woods Preserve, and within 6 mi (10 km) of Kirk Park Beach and South Edison Beach. ...

                    The Hermitage$247

                    The Hermitage$247
                    Sleep Inn & Suites

                    Sleep Inn & Suites

                    5 King Arthur Dr, Niantic
                      2.5 out of 5.0
                       
                       
                      3.6 out of 5 (31 reviews)

                      Situated in Niantic, this hotel is within 3 mi (5 km) of Cedar Ridge Golf Course, Childrens Museum of Southeastern Connecticut, and Hole-in-the-Wall Beach. McCook ...

                      Sleep Inn & Suites$85

                      Sleep Inn & Suites$85
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      * Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.