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Charles Town Vacations

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

Hotwire can help you find your travel bliss with Charles Town 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 Charles Town

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 Charles Town 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 Charles Town well.

Charles Town Flight + Hotel packages

Top Hotel Deals

See all 105 Hotels in Charles Town
Hampton Inn and Suites Charles Town

Hampton Inn and Suites Charles Town

157 Pimlico Dr, Charles Town
    2.5 out of 5.0
     
     

    Located in the heart of Charles Town, this hotel is within 2 mi (3 km) of Charles Town Library, Jefferson County Courthouse, and Old Opera House. Gibson-Todd ...

    Hampton Inn and Suites Charles Town$119

    Hampton Inn and Suites Charles Town$119
    Americas Best Value Inn-Charles Town

    Americas Best Value Inn-Charles Town

    807 Willow Spring Dr, Charles Town
      1.5 out of 5.0
       
       

      Situated in Charles Town, this motel is within 1 mi (2 km) of Charles Town Library, Jefferson County Courthouse, and Old Opera House. Gibson-Todd House and Sleepy ...

      Americas Best Value Inn-Charles Town$55

      Americas Best Value Inn-Charles Town$55
      Hillbrook Inn

      Hillbrook Inn

      4490 Summit Point Road, Charles Town
        3.0 out of 5.0
         
         

        Situated near the airport, this romantic bed & breakfast is 3 mi (4.8 km) from Summit Point Raceway and 3 mi (4.8 km) from Winchester Visitors Center. Locust ...

        Motel 6 Charles Town, WV

        Motel 6 Charles Town, WV

        106 Jefferson Terrace Road, Charles Town
          2.0 out of 5.0
           
           

          Situated in Charles Town, this motel is within 2 mi (3 km) of Charles Town Library, Jefferson County Courthouse, and Sleepy Hollow Country Club. Old Opera House ...

          Motel 6 Charles Town, WV$70

          Motel 6 Charles Town, WV$70
          Rodeway Inn & Suites

          Rodeway Inn & Suites

          741 E Washington St, Charles Town
            2.0 out of 5.0
             
             

            Situated in the entertainment district, this motel is within a 15-minute walk of Charles Town Library, Jefferson County Courthouse, and Old Opera House. Gibson-Todd ...

            Rodeway Inn & Suites$90

            Rodeway Inn & Suites$90
            The Carriage Inn B&B

            The Carriage Inn B&B

            417 E Washington Street, Charles Town
              3.5 out of 5.0
               
               

              Situated in Charles Town, this bed & breakfast is within a 10-minute walk of Charles Town Library, Jefferson County Courthouse, and Old Opera House. Gibson-Todd ...

              Clarion Inn Harpers Ferry - Charles Town

              Clarion Inn Harpers Ferry - Charles Town

              4328 William L Wilson Fwy, Harpers Ferry
                3.0 out of 5.0
                 
                 

                Located in the heart of Harpers Ferry, this hotel is 0.7 mi (1.2 km) from Civil War Living History Museum and within 3 mi (5 km) of Appalachian Trail Conservancy ...

                Clarion Inn Harpers Ferry - Charles Town$99

                Clarion Inn Harpers Ferry - Charles Town$99
                La Quinta Inn & Suites Winchester

                La Quinta Inn & Suites Winchester

                1055 Millwood Pike, Route 50 East, Winchester
                  3.0 out of 5.0
                   
                   

                  Situated in the suburbs, this hotel is within 1 mi (2 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

                  La Quinta Inn & Suites Winchester$99

                  La Quinta Inn & Suites Winchester$99
                  Country Inn & Suites by Radisson, Winchester, VA

                  Country Inn & Suites by Radisson, Winchester, VA

                  141 Kernstown Commons Blvd, Winchester
                    3.0 out of 5.0
                     
                     

                    Situated in Winchester, this hotel is within 6 mi (10 km) of The Kernstown Battlefield, Shenandoah University, and Rock Harbor Golf Course. Shenandoah Valley ...

                    Country Inn & Suites by Radisson, Winchester, VA$71

                    Country Inn & Suites by Radisson, Winchester, VA$71
                    Clarion Hotel & Conference Center Leesburg

                    Clarion Hotel & Conference Center Leesburg

                    1500 E Market St, Leesburg
                      2.5 out of 5.0
                       
                       

                      This family-friendly Leesburg hotel is located near the airport, 2.6 mi (4.2 km) from Leesburg Corner Premium Outlets, and within 6 mi (10 km) of Balls Bluff ...

                      Clarion Hotel & Conference Center Leesburg$102

                      Clarion Hotel & Conference Center Leesburg$102

                      Top Flight Deals

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