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Shaftsbury Vacations

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

Hotwire can help you find your travel bliss with Shaftsbury 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 Shaftsbury

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 Shaftsbury 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 Shaftsbury well.

Top Hotel Deals

See all 194 Hotels in Shaftsbury
Governor's Rock Motel

Governor's Rock Motel

4325 Historic Route 7a, Shaftsbury
    2.0 out of 5.0
     
     

    Situated in Shaftsbury, this motel is 0.8 mi (1.2 km) from Shaftsbury Historical Society Museum and 2.3 mi (3.6 km) from Lake Shaftsbury State Park. Howard Park ...

    Paradise Inn

    Paradise Inn

    141 West Main Street, Bennington
      2.5 out of 5.0
       
       

      Located near the slopes, this Bennington hotel is in the city center and within 1 mi (2 km) of Bennington Museum, Bennington Arts Guild Gallery, and Old First ...

      Paradise Inn$86

      Paradise Inn$86
      The Orchards Hotel

      The Orchards Hotel

      222 Adams Rd, Williamstown
        3.5 out of 5.0
         
         

        Situated in a rural location, this hotel is within 1 mi (2 km) of Hopkins Observatory, Williams College Museum of Art, and Chapin Library of Rare Books and Manuscripts. ...

        The Orchards Hotel$159

        The Orchards Hotel$159
        Palmer House Resort

        Palmer House Resort

        5383 Main St, Manchester Center
          3.0 out of 5.0
           
           

          Located in the heart of Manchester Center, this golf hotel is within a 15-minute walk of Gander Gallery and Manchester Designer Outlets. Dana L. Thompson Memorial ...

          Palmer House Resort$98

          Palmer House Resort$98
          Berkshire Hills Country Inn

          Berkshire Hills Country Inn

          1146 Cold Spring Road, Williamstown
            2.5 out of 5.0
             
             

            Situated in Williamstown, this hotel is within 3 mi (5 km) of Williamstown Historical Museum, Waubeeka Golf Links, and 62 Center for Theater and Dance. Chapin ...

            Holiday Inn Berkshires

            Holiday Inn Berkshires

            40 Main St, North Adams
              3.0 out of 5.0
               
               

              Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library, and Western Gateway Heritage State Park. ...

              Holiday Inn Berkshires$111

              Holiday Inn Berkshires$111
              Hampton Inn and Suites Manchester

              Hampton Inn and Suites Manchester

              4519 Main St, Manchester
                2.5 out of 5.0
                 
                 

                Situated in the city center, this hotel is close to Manchester Designer Outlets, Orvis Fly Fishing, and American Museum of Fly Fishing. Also nearby are Southern ...

                Hampton Inn and Suites Manchester$127

                Hampton Inn and Suites Manchester$127
                Mount Snow Condominiums

                Mount Snow Condominiums

                89 Grand Summit Way, West Dover
                  3.5 out of 5.0
                   
                   

                  Conveniently located near the ski slopes, this West Dover condo building is 0.2 mi (0.4 km) from Mount Snow and within 16 mi (25 km) of Mount Snow Golf Course ...

                  The Williams Inn

                  The Williams Inn

                  1090 Main Street, Williamstown
                    3.0 out of 5.0
                     
                     

                    Situated in Williamstown, this hotel is within a 5-minute walk of Williamstown Historical Museum and 62 Center for Theater and Dance. Chapin Library of Rare ...

                    The Williams Inn$94

                    The Williams Inn$94
                    Inns at the Equinox

                    Inns at the Equinox

                    3567 Main Street Route 7A, Manchester
                      3.0 out of 5.0
                       
                       

                      Situated in Manchester, this spa hotel is within a 10-minute walk of American Museum of Fly Fishing and Orvis Fly Fishing. Southern Vermont Arts Center and Equinox ...

                      Inns at the Equinox$130

                      Inns at the Equinox$130

                      Top Flight Deals

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