Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Top Chestertown Hotels Deals

See all 107 Properties in Chestertown
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.

    Driftwood Inn$129

    Driftwood Inn$129
    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 27 mi (43.5 km) from Queenstown Premium Outlets.

      Holiday Inn Express Hotel & Suites Chestertown$100

      Holiday Inn Express Hotel & Suites Chestertown$100
      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.

        Inn at Mitchell House$150

        Inn at Mitchell House$150
        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 25.9 mi (41.7 km) from Queenstown Premium Outlets.

          John L Stam House$190

          John L Stam House$190
          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.

            Great Oak Manor$219

            Great Oak Manor$219
            Quality Suites

            Quality Suites

            160 Scheeler Rd, Chestertown
              2.5 out of 5.0
               
               

              Situated in Chestertown, this hotel is 0.6 mi (1 km) from Washington College and 27 mi (43.5 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$85

                Best Western Plus Hotel & Conference Center$85
                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 Double Rock Park and Boordy Vineyards. ...

                  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$59

                    Red Roof Inn Aberdeen$59
                    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 1.1 mi (1.7 km) from Kent Island and within 12 mi (20 km) of Queenstown Premium Outlets and Chesapeake Bay Bridge. Sandy ...

                      Best Western Kent Narrows Inn$99

                      Best Western Kent Narrows Inn$99