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Shepherdstown Vacations

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

Hotwire can help you find your travel bliss with Shepherdstown 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 Shepherdstown

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 Shepherdstown 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 Shepherdstown well.

Top Hotel Deals

See all 117 Hotels in Shepherdstown
Bavarian Inn

Bavarian Inn

164 Shepherd Grade Rd, Shepherdstown
    3.5 out of 5.0
     
     

    Situated in Shepherdstown, this hotel is within a 10-minute walk of Shepherd University, Shepherdstown Museum, and Shepherdstown Opera House. Rumsey Steamboat ...

    Clarion Hotel & Conference Center

    Clarion Hotel & Conference Center

    233 Lowe Dr, Shepherdstown
      3.0 out of 5.0
       
       

      Situated near the airport, this hotel is within a 15-minute walk of Shepherdstown Opera House, Morgan's Grove Park, and Shepherdstown Museum. Rumsey Steamboat ...

      Thomas Shepherd Inn

      Thomas Shepherd Inn

      300 West German St, Shepherdstown
        3.5 out of 5.0
         
         

        Located in the heart of Shepherdstown, this bed & breakfast is within a 5-minute walk of Shepherdstown Opera House, Shepherdstown Museum, and Shepherd University. ...

        Quality Inn

        Quality Inn

        70 Maddex Square Dr, Shepherdstown
          2.5 out of 5.0
           
           

          Situated in Shepherdstown, this hotel is within a 15-minute walk of Shepherdstown Opera House, Shepherd University, and Shepherdstown Museum. Rumsey Steamboat ...

          Country Inn & Suites by Radisson, Hagerstown, MD

          Country Inn & Suites by Radisson, Hagerstown, MD

          17612 Valley Mall Rd, Hagerstown
            3.0 out of 5.0
             
             

            Situated in Hagerstown, this hotel is within 9 mi (15 km) of Maryland Theater, Hagerstown Premium Outlets, and Hagerstown Speedway. Martins Mill Bridge and Antietam ...

            Country Inn & Suites by Radisson, Hagerstown, MD$84

            Country Inn & Suites by Radisson, Hagerstown, MD$84
            Days Inn by Wyndham Frederick

            Days Inn by Wyndham Frederick

            5646 Buckeystown Pike, Frederick
              2.0 out of 5.0
               
               

              Situated in Frederick, this hotel is within 1 mi (2 km) of Francis Scott Key Mall, Westview Promenade, and Harry Grove Stadium. Monocacy National Battlefied ...

              Days Inn by Wyndham Frederick$63

              Days Inn by Wyndham Frederick$63
              Best Western Historic Frederick

              Best Western Historic Frederick

              420 Prospect Blvd, Frederick
                2.5 out of 5.0
                 
                 

                Situated in Frederick, this hotel is within 3 mi (5 km) of National Museum of Civil War Medicine, Harry Grove Stadium, and Frederick Fairgrounds. Francis Scott ...

                Best Western Historic Frederick$79

                Best Western Historic Frederick$79
                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
                  Super 8 by Wyndham Frederick

                  Super 8 by Wyndham Frederick

                  20 Monocacy Blvd, Frederick
                    2.0 out of 5.0
                     
                     

                    Situated in Frederick, this hotel is within 1 mi (2 km) of Harry Grove Stadium and National Museum of Civil War Medicine. Frederick Fairgrounds and Francis Scott ...

                    Super 8 by Wyndham Frederick$51

                    Super 8 by Wyndham Frederick$51
                    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

                      Top Flight Deals

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