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Vineyard Haven Vacations

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

Hotwire can help you find your travel bliss with Vineyard Haven 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 Vineyard Haven

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 Vineyard Haven 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 Vineyard Haven well.

Top Hotel Deals

See all 294 Hotels in Vineyard Haven
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 ...

    Clark House at the Twin Oaks Inn

    Clark House at the Twin Oaks Inn

    20 Edgartown Road, Vineyard Haven
      3.0 out of 5.0
       
       

      Situated near the beach, this bed & breakfast is within a 10-minute walk of Martha's Vineyard Chamber of Commerce and Vineyard Playhouse. Martha's Vineyard Film ...

      Thorncroft Inn

      Thorncroft Inn

      460 Main St, Vineyard Haven
        3.0 out of 5.0
         
         

        Situated near the beach, this bed & breakfast is within a 15-minute walk of Tisbury Town Beach and Vineyard Haven Public Library. Vineyard Playhouse and West ...

        Hanover House at the Twin Oaks Inn

        Hanover House at the Twin Oaks Inn

        28 Edgartown Road, Vineyard Haven
          3.0 out of 5.0
           
           

          Situated near the beach, this bed & breakfast is within a 10-minute walk of Martha's Vineyard Chamber of Commerce and Vineyard Playhouse. Martha's Vineyard Film ...

          The 1720 House

          The 1720 House

          152 Main Street, Vineyard Haven
            2.5 out of 5.0
             
             

            Situated in Tisbury, this bed & breakfast is within a 5-minute walk of Vineyard Haven Public Library and Vineyard Playhouse. Martha's Vineyard Chamber of Commerce ...

            The Vacation House

            The Vacation House

            183 Skiff Avenue, Vineyard Haven
              3.5 out of 5.0
               
               

              Situated in Tisbury, this vacation home is within a 15-minute walk of Martha's Vineyard Chamber of Commerce and Martha's Vineyard Film Center. Vineyard Playhouse ...

              Nature's Pocket

              Nature's Pocket

              9 Sylvan Avenue, Vineyard Haven
                3.5 out of 5.0
                 
                 

                Situated in Tisbury, this vacation home is within 2 mi (3 km) of Martha's Vineyard Chamber of Commerce, Island Cove Adventures, and Vineyard Playhouse. Martha's ...

                The CAVU Mansion on Bellevue

                The CAVU Mansion on Bellevue

                20 Bellevue Ave, Vineyard Haven
                  3.5 out of 5.0
                   
                   

                  Situated in Tisbury, this vacation home is within 2 mi (3 km) of Martha's Vineyard Chamber of Commerce, Island Cove Adventures, and Vineyard Playhouse. Martha's ...

                  The Looks Pond Garden House

                  The Looks Pond Garden House

                  42 Looks Pond Way, Vineyard Haven
                    3.5 out of 5.0
                     
                     

                    Situated in Vineyard Haven, this vacation home is 1.6 mi (2.6 km) from Polly Hill Arboretum and within 6 mi (10 km) of Long Point Wildlife Refuge and Lucy Vincent ...

                    The Happy Place

                    The Happy Place

                    75 Oklahoma Avenue, Vineyard Haven
                      3.5 out of 5.0
                       
                       

                      Situated in Tisbury, this vacation home is within 2 mi (3 km) of Martha's Vineyard Chamber of Commerce, Island Cove Adventures, and Vineyard Playhouse. Martha's ...

                      Top Flight Deals

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