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Chestertown Vacations

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

Hotwire can help you find your travel bliss with Chestertown 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 Chestertown

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 Chestertown 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 Chestertown well.

Top Hotel Deals

See all 102 Hotels in Chestertown
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
    2.5 out of 5.0
     
     

    Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 25.2 mi (40.5 km) from Queenstown Premium Outlets.

    Holiday Inn Express Hotel & Suites Chestertown$113

    Holiday Inn Express Hotel & Suites Chestertown$113
    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown
      2.0 out of 5.0
       
       

      Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.

      Inn at Mitchell House

      Inn at Mitchell House

      8796 Maryland Pkwy, Chestertown
        3.0 out of 5.0
         
         

        Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College.

        John L Stam House

        John L Stam House

        114 Washington Ave, Chestertown
          3.0 out of 5.0
           
           

          Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from Queenstown Premium Outlets.

          Great Oak Manor

          Great Oak Manor

          10568 Cliff Rd, Chestertown
            3.5 out of 5.0
             
             

            Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.

            Quality Suites

            Quality Suites

            160 Scheeler Rd, Chestertown
              2.5 out of 5.0
               
               

              Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 25.4 mi (40.9 km) from Queenstown Premium Outlets.

              Best Western Plus Hotel & Conference Center

              Best Western Plus Hotel & Conference Center

              5625 O'Donnell Street, Baltimore
                3.0 out of 5.0
                 
                 

                The Best Western Plus is located just off highway I-95 and 3.8 miles (6.1 km) from Baltimore's port and Cruise Terminal. Little Italy’s restaurants, cafés, and ...

                Best Western Plus Hotel & Conference Center$93

                Best Western Plus Hotel & Conference Center$93
                Home2 Suites by Hilton Baltimore/White Marsh

                Home2 Suites by Hilton Baltimore/White Marsh

                10465 Philadelphia Road, White Marsh
                  2.5 out of 5.0
                   
                   

                  Situated in the entertainment district, this hotel is 2.2 mi (3.6 km) from White Marsh Mall and within 12 mi (20 km) of Towson University and Double Rock Park. ...

                  Home2 Suites by Hilton Baltimore/White Marsh$96

                  Home2 Suites by Hilton Baltimore/White Marsh$96
                  Red Roof Inn Aberdeen

                  Red Roof Inn Aberdeen

                  988 Hospitality Way, Aberdeen
                    2.0 out of 5.0
                     
                     

                    Situated in a shopping district, this hotel is 1.7 mi (2.8 km) from Ripken Stadium and 1.8 mi (3 km) from Cal Ripken Museum. Aberdeen Proving Ground and Bulle ...

                    Red Roof Inn Aberdeen$55

                    Red Roof Inn Aberdeen$55
                    Best Western Kent Narrows Inn

                    Best Western Kent Narrows Inn

                    3101 Main Street, Grasonville
                      2.5 out of 5.0
                       
                       

                      Situated in Grasonville, this motel is within 12 mi (20 km) of Queenstown Premium Outlets, Chesapeake Bay Bridge, and Sandy Point State Park. U.S. Naval Academy ...

                      Best Western Kent Narrows Inn$99

                      Best Western Kent Narrows Inn$99

                      Top Flight Deals

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