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Shelter Island Vacations

Pack those stellar shades. We have Shelter Island 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 – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Shelter Island 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

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 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 well.

Shelter Island Flight + Hotel packages

Top Hotel Deals

See all 276 Hotels in Shelter Island
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 ...

    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 $210

      Water's Edge Resort & Spa $210
      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$127

        The Atlantic Hotel$127
        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. 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 ...

            Aqualina Inn Montauk

            Aqualina Inn Montauk

            20 South Elmwood Avenue, Montauk
              2.5 out of 5.0
               
               

              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 ...

              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. ...

                Sleep Inn & Suites

                Sleep Inn & Suites

                5 King Arthur Dr, Niantic
                  2.5 out of 5.0
                   
                   

                  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$89

                  Sleep Inn & Suites$89
                  Topping Rose House

                  Topping Rose House

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

                    Situated in Bridgehampton, this luxury hotel is within a 15-minute walk of South Fork Natural History Museum and Nature Center and Children's Museum of The East ...

                    Motel 6 New London - Niantic

                    Motel 6 New London - Niantic

                    269 Flanders Rd, Niantic
                      2.0 out of 5.0
                       
                       

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

                      Motel 6 New London - Niantic$47

                      Motel 6 New London - Niantic$47

                      Top Flight Deals

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