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

Shelter Island Heights Vacations

Pack those stellar shades. We have Shelter Island Heights vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Shelter Island Heights – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Shelter Island Heights vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Shelter Island Heights

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Shelter Island Heights vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Shelter Island Heights well.

Shelter Island Heights Flight + Hotel packages

Top Hotel Deals

See all 230 Hotels in Shelter Island Heights
The Pridwin Hotel

The Pridwin Hotel

81 Shore Road, Shelter Island Heights
    3.0 out of 5.0
     
     

    Nestled on the beach, this Shelter Island Heights hotel is within a 10-minute walk of Shelter Island Tennis Club and Crescent Beach. Sunset Beach and Shelter ...

    Shelter Island House

    Shelter Island House

    11 Stearns Point Rd, Shelter Island Heights
      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 ...

      The Chequit Inn

      The Chequit Inn

      23 Grand Ave, Shelter Island Heights
        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 Sylvester Manor. Crescent Beach and East End Seaport ...

        House on Chase Creek

        House on Chase Creek

        3 Locust Avenue, Shelter Island Heights
          2.5 out of 5.0
           
           

          Situated near the beach, this bed & breakfast is within 1 mi (2 km) of Shelter Island Country Club and Sunset Beach. Sylvester Manor and Crescent Beach are also ...

          West Neck Guesthouse

          West Neck Guesthouse

          31 W Neck Rd, Shelter Island Heights
            3.5 out of 5.0
             
             

            Situated in Shelter Island Heights, this bed & breakfast is close to Shelter Island Country Club, Sunset Beach, and Crescent Beach. Also nearby are Sylvester ...

            Dering Harbor Inn

            Dering Harbor Inn

            13 Winthrop Road, Shelter Island Heights
              2.5 out of 5.0
               
               

              Situated near the beach in Shelter Island Heights, this condo resort is close to Sylvester Manor, Shelter Island Country Club and Shelter Island Whale's Tail. ...

              SEVEN - Shelter Island Guest House

              SEVEN - Shelter Island Guest House

              7 Stearns Point Road, Shelter Island Heights
                3.5 out of 5.0
                 
                 

                Situated by the ocean, this bed & breakfast is within a 10-minute walk of Sunset Beach and Shelter Island Country Club. Crescent Beach and Shelter Island Tennis ...

                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$189

                  The Atlantic Hotel$189
                  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 $179

                    Water's Edge Resort & Spa $179
                    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 ...

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.