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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 29 Hotels in Bennington
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

401 Winchester St, Keene
    3.0 out of 5.0
     
     

    This family-friendly Keene hotel is located in the suburbs, within 1 mi (2 km) of Thorne-Sagendorph Art Gallery, Cheshire Children's Museum, and Historical Society ...

    Best Western Plus Keene Hotel$85

    Best Western Plus Keene Hotel$85
    Courtyard by Marriott Keene Downtown

    Courtyard by Marriott Keene Downtown

    75 Railroad St, Keene
      3.0 out of 5.0
       
       

      Situated in Historic Main Street, this hotel is within a 5-minute walk of Colonial Theatre and Central Square. Horatio Colony Museum and Historical Society of ...

      Courtyard by Marriott Keene Downtown$98

      Courtyard by Marriott Keene Downtown$98
      Fairfield Inn & Suites by Marriott Keene Downtown

      Fairfield Inn & Suites by Marriott Keene Downtown

      30 Main Street, Keene
        3.0 out of 5.0
         
         

        Located in the heart of Historic Main Street, this hotel is steps from Central Square and Colonial Theatre. Horatio Colony Museum and Historical Society of Cheshire ...

        Fairfield Inn & Suites by Marriott Keene Downtown$98

        Fairfield Inn & Suites by Marriott Keene Downtown$98
        Benjamin Prescott Inn

        Benjamin Prescott Inn

        433 Turnpike Rd, Jaffrey
          3.0 out of 5.0
           
           

          Situated in Jaffrey, this bed & breakfast is 2.2 mi (3.6 km) from Jaffrey Civic Center and 2.3 mi (3.7 km) from Cathedral of the Pines. Shattuck Golf Course ...

          The Birchwood Inn

          The Birchwood Inn

          340 Senator Tobey Highway, Temple
            3.5 out of 5.0
             
             

            Situated in Temple, this inn is 3.1 mi (4.9 km) from Miller State Park and within 9 mi (15 km) of Pack Monadnock Mountain and The Monadnock Center for History ...

            Crotched Mountain Resort

            Crotched Mountain Resort

            740 2nd Nh Tpke N, Francestown
              3.0 out of 5.0
               
               

              Situated in Francestown, this golf condo building is 11 mi (17.6 km) from Harris Center for Conservation Education and 11.9 mi (19.1 km) from Peterborough Players. ...

              Crotched Mountain Resort$99

              Crotched Mountain Resort$99
              The Maples at Warner

              The Maples at Warner

              69 East Main Street, Warner
                3.0 out of 5.0
                 
                 

                Situated in Warner, this bed & breakfast is 0.2 mi (0.3 km) from New Hampshire Telephone Museum and 1.5 mi (2.3 km) from Mt. Kearsarge Indian Museum. Rollins ...

                Jack Daniels Motor Inn

                Jack Daniels Motor Inn

                80 Concord Street, Peterborough
                  2.5 out of 5.0
                   
                   

                  Situated in Peterborough, this hotel is within a 15-minute walk of Mariposa Museum and World Cultures Center, Peterborough Town House, and The Monadnock Center ...

                  The Monadnock Inn

                  The Monadnock Inn

                  379 Main Street, Jaffrey
                    2.5 out of 5.0
                     
                     

                    Situated in the mountains, this bed & breakfast is 0.7 mi (1.1 km) from Shattuck Golf Course and within 3 mi (5 km) of Jaffrey Civic Center and Monadnock State ...

                    Henniker Motel

                    Henniker Motel

                    61 Craney Pond Rd, Henniker
                      2.0 out of 5.0
                       
                       

                      Situated in Henniker, this motel is 0.2 mi (0.4 km) from Pats Peak and 11.9 mi (19.1 km) from Franklin Pierce Homestead. Stonebridge Golf Course and Capitol ...

                      Top Flight Deals

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