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Bennington Vacations

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

Hotwire can help you find your travel bliss with Bennington 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 Bennington

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 Bennington 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 Bennington well.

Top Hotel Deals

See all 403 Hotels in Bennington
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
    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
      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
        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
          Best Western Bennington

          Best Western Bennington

          220 Northside Drive, Bennington
            2.5 out of 5.0
             
             

            Situated in Bennington, this hotel is within 2 mi (3 km) of Bennington Battle Monument, Old First Congregational Church, and Bennington Museum. Bennington Arts ...

            Best Western Bennington$98

            Best Western Bennington$98
            Hampton Inn Bennington

            Hampton Inn Bennington

            51 Hannaford Square, Bennington
              2.5 out of 5.0
               
               

              Situated in Bennington, this hotel is within 3 mi (5 km) of Bennington College, Park McCullough House, and Old First Congregational Church. Bennington Battle ...

              Hampton Inn Bennington$134

              Hampton Inn Bennington$134
              Bennington Motor Inn

              Bennington Motor Inn

              143 West Main Street, Bennington
                2.0 out of 5.0
                 
                 

                Located in the heart of Bennington, this motel is within a 10-minute walk of Bennington Museum and Bennington Arts Guild Gallery. Old First Congregational Church ...

                Bennington Motor Inn$71

                Bennington Motor Inn$71
                Kimpton Taconic Hotel

                Kimpton Taconic Hotel

                3835 Main St., Manchester
                  4.0 out of 5.0
                   
                   

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

                  Kimpton Taconic Hotel$135

                  Kimpton Taconic Hotel$135
                  Four Winds Country Motel

                  Four Winds Country Motel

                  7379 Main Street, Manchester Center
                    2.0 out of 5.0
                     
                     

                    Situated in Manchester Center, this motel is within 3 mi (5 km) of Gander Gallery, Manchester Designer Outlets, and Dana L. Thompson Memorial Park. Orvis Fly ...

                    Econo Lodge

                    Econo Lodge

                    2187 Depot St, Manchester Center
                      2.5 out of 5.0
                       
                       

                      Situated in the mountains, this motel is within 3 mi (5 km) of Gander Gallery, Manchester Designer Outlets, and Dana L. Thompson Memorial Park. Orvis Fly Fishing ...

                      Econo Lodge$100

                      Econo Lodge$100

                      Top Flight Deals

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