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Chappaquiddick Island Vacations

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

Hotwire can help you find your travel bliss with Chappaquiddick 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 Chappaquiddick 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 Chappaquiddick 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 Chappaquiddick Island well.

Top Hotel Deals

See all 408 Properties in Chappaquiddick Island
Briar Patch

Briar Patch

300 Chappaquiddick Road, Edgartown
    3.5 out of 5.0
     
     

    Situated in Edgartown, this vacation home is within 1 mi (2 km) of Mytoi Garden and Chappaquidick Dike Bridge. Norton Point Beach and Wasque Beach are also within ...

    Sea Crest Beach Hotel

    Sea Crest Beach Hotel

    350 Quaker Rd, North Falmouth
      3.0 out of 5.0
       
       

      This North Falmouth hotel is on the beach, 0.2 mi (0.3 km) from Old Silver Beach, and within 6 mi (10 km) of Wood Neck Beach and Cataumet Arts Center. Falmouth ...

      Sea Crest Beach Hotel$278

      Sea Crest Beach Hotel$278
      Hyannis Travel Inn

      Hyannis Travel Inn

      18 North St, Hyannis
        2.0 out of 5.0
         
         

        Located in the heart of Hyannis, this hotel is steps from John F. Kennedy Hyannis Museum and Cape Cod Baseball Hall of Fame. Cape Cod Maritime Museum and Cape ...

        Hyannis Travel Inn$115

        Hyannis Travel Inn$115
        Anchor In Distinctive Waterfront Lodging

        Anchor In Distinctive Waterfront Lodging

        1 South Street, Hyannis
          3.0 out of 5.0
           
           

          Situated on the waterfront, this hotel is within a 10-minute walk of Cape Cod Maritime Museum and Hyannis Harbor. John F. Kennedy Hyannis Museum and Cape Cod ...

          Anchor In Distinctive Waterfront Lodging$299

          Anchor In Distinctive Waterfront Lodging$299
          Harbor View Hotel

          Harbor View Hotel

          131 N Water Street Marthas Vineyard, Edgartown
            3.5 out of 5.0
             
             

            Situated near the airport, this historic hotel is within a 5-minute walk of Lighthouse Beach and Edgartown Lighthouse. Edgartown Public Library and Old Whaling ...

            Harbor View Hotel$244

            Harbor View Hotel$244
            Kelley House

            Kelley House

            23 Kelly Street, Edgartown
              3.0 out of 5.0
               
               

              Located in the heart of Edgartown, this hotel is within a 5-minute walk of Edgartown Public Library, Old Whaling Church, and Vincent House Museum. Martha's Vineyard ...

              Kelley House$369

              Kelley House$369
              Americas Best Value Inn and Suites Hyannis/Cape Cod

              Americas Best Value Inn and Suites Hyannis/Cape Cod

              206 Main St, Hyannis
                2.0 out of 5.0
                 
                 

                Located in the heart of Hyannis, this hotel is within a 10-minute walk of Cape Cod Maritime Museum, John F. Kennedy Hyannis Museum, and Cape Cod Baseball Hall ...

                Americas Best Value Inn and Suites Hyannis/Cape Cod$71

                Americas Best Value Inn and Suites Hyannis/Cape Cod$71
                Heritage House Hotel

                Heritage House Hotel

                259 Main Street, Hyannis
                  2.5 out of 5.0
                   
                   

                  Heritage House Hotel$87

                  Heritage House Hotel$87
                  Hyannis Harbor Hotel

                  Hyannis Harbor Hotel

                  213 Ocean St, Hyannis
                    3.5 out of 5.0
                     
                     

                    Located on Hyannis Harbor, this hotel overlooks the Nantucket and Martha's Vineyard ferries; the JFK Memorial is 1 block away.

                    Hyannis Harbor Hotel$206

                    Hyannis Harbor Hotel$206
                    Mansion House Inn And Spa

                    Mansion House Inn And Spa

                    9 Main Street, Vineyard Haven
                      3.5 out of 5.0
                       
                       

                      Located in the heart of Vineyard Haven, this spa hotel is within a 5-minute walk of Martha's Vineyard Chamber of Commerce and Vineyard Playhouse. Martha's Vineyard ...

                      Mansion House Inn And Spa$369

                      Mansion House Inn And Spa$369

                      Top Flight Deals

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