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Charlestown Vacations

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

Hotwire can help you find your travel bliss with Charlestown 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 Charlestown

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 Charlestown 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 Charlestown well.

Charlestown Flight + Hotel packages

Top Hotel Deals

See all 184 Hotels in Charlestown
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$100

    Best Western Plus Keene Hotel$100
    Holiday Inn Express Springfield

    Holiday Inn Express Springfield

    818 Charlestown Rd, Springfield
      2.5 out of 5.0
       
       

      Situated in a rural location, this hotel is within a 15-minute walk of Baltimore Covered Bridge and Eureka Schoolhouse. The Fort at No.4 Open Air Museum is 1.3 ...

      Holiday Inn Express Springfield$110

      Holiday Inn Express Springfield$110
      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$116

        Courtyard by Marriott Keene Downtown$116
        Days Inn by Wyndham Keene NH

        Days Inn by Wyndham Keene NH

        3 Ash Brook Road, Keene
          2.0 out of 5.0
           
           

          Situated in Keene, this hotel is within 2 mi (3 km) of Cheshire Children's Museum, Thorne-Sagendorph Art Gallery, and Alumni Field. Horatio Colony Museum and ...

          Days Inn by Wyndham Keene NH$80

          Days Inn by Wyndham Keene NH$80
          Jackson Gore Inn

          Jackson Gore Inn

          111 Jackson Gore Road, Ludlow
            3.0 out of 5.0
             
             

            This Ludlow condo building is in the mountains, offering ski-in/ski-out access within 3 mi (5 km) of Okemo Valley Golf Club and Okemo Mountain Resort and close ...

            Jackson Gore Inn$159

            Jackson Gore Inn$159
            The Upper Pass Lodge at Magic Mountain

            The Upper Pass Lodge at Magic Mountain

            420 Magic Mountain Access Road, Londonderry
              2.5 out of 5.0
               
               

              Conveniently near skiing facilities, this Londonderry motel is located in the mountains within 3 mi (5 km) of Magic Mountain Ski Resort, Viking Nordic Center, ...

              The Upper Pass Lodge at Magic Mountain$42

              The Upper Pass Lodge at Magic Mountain$42
              The Putney Inn

              The Putney Inn

              57 Putney Landing Rd, Putney
                2.5 out of 5.0
                 
                 

                Situated in Putney, this motel is 0.4 mi (0.6 km) from Yellow Barn and within 9 mi (15 km) of United States Navy Seabee Bridge and Brattleboro Common. Madame ...

                The Putney Inn$120

                The Putney Inn$120
                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$107

                  Fairfield Inn & Suites by Marriott Keene Downtown$107
                  Sunapee Lake Lodge

                  Sunapee Lake Lodge

                  1403 Route 103, Newbury
                    2.5 out of 5.0
                     
                     

                    Situated in the mountains, this hotel is 2 mi (3.2 km) from Mount Sunapee and within 6 mi (10 km) of The Fells and Newport Historical Society. Newport Golf Club ...

                    Sunapee Lake Lodge$99

                    Sunapee Lake Lodge$99
                    Timber Inn Motel

                    Timber Inn Motel

                    112 Route 103 S, Ludlow
                      2.5 out of 5.0
                       
                       

                      Situated on a river, this hotel is close to Dorsey Park, Okemo Mountain Resort, and Okemo Valley Golf Club. Area attractions also include Buttermilk Falls and ...

                      Top Flight Deals

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