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Chilmark Vacations

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

Hotwire can help you find your travel bliss with Chilmark 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 Chilmark

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 Chilmark 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 Chilmark well.

Top Hotel Deals

See all 213 Hotels in Chilmark
Menemsha Inn & Cottages

Menemsha Inn & Cottages

12 Menemsha Inn Rd, Chilmark
    3.0 out of 5.0
     
     

    Situated on the waterfront, this inn is 0.7 mi (1.2 km) from Menemsha Beach and 2 mi (3.2 km) from Lucy Vincent Beach. Polly Hill Arboretum and Gay Head Lighthouse ...

    The Bird s Nest

    The Bird s Nest

    260 South Rd, Chilmark
      3.5 out of 5.0
       
       

      Situated in Chilmark, this vacation home is 1.8 mi (2.9 km) from Lucy Vincent Beach and within 6 mi (10 km) of Polly Hill Arboretum and Menemsha Beach. Long ...

      Sweet Island Child

      Sweet Island Child

      47 State Rd, Chilmark
        3.5 out of 5.0
         
         

        Situated in Chilmark, this vacation home is 1.1 mi (1.8 km) from Lucy Vincent Beach and 2.1 mi (3.3 km) from Menemsha Beach. Gay Head Lighthouse and Aquinnah ...

        The Eliot Noyes

        The Eliot Noyes

        4 Glacier Glen, Chilmark
          3.5 out of 5.0
           
           

          Situated in Chilmark, this lodge is 1.4 mi (2.2 km) from Lucy Vincent Beach and 2.4 mi (3.9 km) from Menemsha Beach. Polly Hill Arboretum and Gay Head Lighthouse ...

          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 mi (0.1 km) from Old Silver Beach, and within 6 mi (10 km) of Wood Neck Beach and Cataumet Arts Center. Falmouth ...

            Sea Crest Beach Hotel$169

            Sea Crest Beach Hotel$169
            Harbor View Hotel

            Harbor View Hotel

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

              This family-friendly Edgartown hotel is located near the airport, within a 5-minute walk of Edgartown Lighthouse and Lighthouse Beach. Vincent House Museum and ...

              Harbor View Hotel$249

              Harbor View Hotel$249
              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$199

                Kelley House$199
                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 Tisbury, this spa hotel is within a 5-minute walk of Martha's Vineyard Chamber of Commerce and Vineyard Playhouse. Martha's Vineyard ...

                  Falmouth Inn

                  Falmouth Inn

                  824 Main Street, Falmouth
                    2.0 out of 5.0
                     
                     

                    Situated in Falmouth, this hotel is within 1 mi (2 km) of Island Queen Ferry, Falmouth Museums on the Green, and Menauhant Beach. Surf Drive Beach and College ...

                    Falmouth Inn$109

                    Falmouth Inn$109
                    Admiralty Inn & Suites

                    Admiralty Inn & Suites

                    51 Teaticket Highway, Falmouth
                      2.0 out of 5.0
                       
                       

                      Located in the heart of Falmouth, this motel is within 2 mi (3 km) of Island Queen Ferry, Menauhant Beach, and Falmouth Museums on the Green. College Light Opera ...

                      Admiralty Inn & Suites$91

                      Admiralty Inn & Suites$91

                      Top Flight Deals

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