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Windham County Vacations

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

Hotwire can help you find your travel bliss with Windham County 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 Windham County

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 Windham County 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 Windham County well.

Top Hotel Deals

See all 144 Hotels in Windham County
Colonial Motel And Spa

Colonial Motel And Spa

889 Putney Rd, Brattleboro
    3.0 out of 5.0
     
     

    Located in the heart of Brattleboro, this motel is 0.7 mi (1.1 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro ...

    Colonial Motel And Spa$69

    Colonial Motel And Spa$69
    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, ...

      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 ...

        Old Red Mill Inn

        Old Red Mill Inn

        18 North Main Street, Wilmington
          2.5 out of 5.0
           
           

          Situated in Wilmington, this inn is close to Adams Family Farm and Molly Stark State Park. Area attractions also include Mount Snow Golf Course and Honora ...

          Hampton Inn Brattleboro

          Hampton Inn Brattleboro

          1378 Putney Road, Brattleboro
            2.5 out of 5.0
             
             

            Situated in Brattleboro, this hotel is 0.7 mi (1.2 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

            Hampton Inn Brattleboro$107

            Hampton Inn Brattleboro$107
            Quality Inn & Conference Center

            Quality Inn & Conference Center

            1380 Putney Road, Brattleboro
              2.5 out of 5.0
               
               

              Situated in Brattleboro, this hotel is 0.8 mi (1.3 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

              Quality Inn & Conference Center$59

              Quality Inn & Conference Center$59
              Holiday Inn Express Hotel & Suites Brattleboro

              Holiday Inn Express Hotel & Suites Brattleboro

              100 Chickering Drive, Brattleboro
                2.5 out of 5.0
                 
                 

                Situated in a rural location, this hotel is 1 mi (1.6 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro ...

                Holiday Inn Express Hotel & Suites Brattleboro$106

                Holiday Inn Express Hotel & Suites Brattleboro$106
                Latchis Hotel

                Latchis Hotel

                50 Main Street, Brattleboro
                  2.5 out of 5.0
                   
                   

                  Situated in Brattleboro, this boutique hotel is within a 15-minute walk of Brattleboro Museum & Art Center and Brattleboro Common. Estey Organ Museum and Vermont ...

                  Riverside Hotel, an Ascend Hotel Collection Member

                  Riverside Hotel, an Ascend Hotel Collection Member

                  20 Riverside Drive, West Chesterfield
                    2.5 out of 5.0
                     
                     

                    Located in the heart of West Chesterfield, this hotel is 0.2 mi (0.3 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Madame Sherris Castle ...

                    Riverside Hotel, an Ascend Hotel Collection Member$129

                    Riverside Hotel, an Ascend Hotel Collection Member$129
                    Super 8 Brattleboro

                    Super 8 Brattleboro

                    1043 Putney Road, Brattleboro
                      2.0 out of 5.0
                       
                       

                      Situated in Brattleboro, this motel is 0.4 mi (0.7 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

                      Super 8 Brattleboro$57

                      Super 8 Brattleboro$57

                      Top Flight Deals

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