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location Chestertown is highly rated for Sports and Universities by 542 people

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Top 10 Hotels in Chestertown

See all 121 Properties in Chestertown
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
John L Stam House
    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.

    $190 per night for 2 guests

    Holiday Inn Express Hotel & Suites Chestertown

    Holiday Inn Express Hotel & Suites Chestertown

    150 Scheeler Road, Chestertown
    Holiday Inn Express Hotel & Suites Chestertown
    • Free Cancellation
    • Reserve now, pay when you stay
    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.

    $83 per night for 2 guests

    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown
    Driftwood Inn
    • Free Cancellation
    • Reserve now, pay when you stay
    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.

    $59 per night for 2 guests

    Great Oak Manor

    Great Oak Manor

    10568 Cliff Rd, Chestertown
    Great Oak Manor
      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.

      $169 per night for 2 guests

      Stunning Home on a 25-acre Private Woodland Estate

      Stunning Home on a 25-acre Private Woodland Estate

      , Chestertown
      Stunning Home on a 25-acre Private Woodland Estate
         
         

        Situated in Chestertown, this historic vacation home is in the same area as Washington College.

        Stunning Home on a 25-acre Private Woodland EstateGet Rates

        Annapolis home with many amenities

        Annapolis home with many amenities

        1013 Magothy Park Ln, Annapolis
        Annapolis home with many amenities
        • Free Cancellation
        • Reserve now, pay when you stay
        3.0 out of 5.0
         
         

        Situated in the suburbs, this villa is close to Sandy Point State Park and Chesapeake Bay Bridge. Area attractions also include U.S. Naval Academy and William ...

        $198 per night for 2 guests

        Extended Stay America Baltimore - Bel Air- Aberdeen

        Extended Stay America Baltimore - Bel Air- Aberdeen

        1361 James Way, Bel Air
        Extended Stay America Baltimore - Bel Air- Aberdeen
        • Free Cancellation
        • Reserve now, pay when you stay
        2.5 out of 5.0
         
         

        Situated in Bel Air, this hotel is within 9 mi (15 km) of Ripken Stadium, Cal Ripken Museum, and Harford Community College. Aberdeen Proving Ground and Liriodendron ...

        $58 per night for 2 guests

        La Quinta Inn & Suites Edgewood / Aberdeen-South

        La Quinta Inn & Suites Edgewood / Aberdeen-South

        2112b Emmorton Park Rd, Edgewood
        La Quinta Inn & Suites Edgewood / Aberdeen-South
        • Free Cancellation
        • Reserve now, pay when you stay
        2.5 out of 5.0
         
         

        Situated in Edgewood, this hotel is within 12 mi (20 km) of Harford Mall, Ripken Stadium, and Harford Community College. Aberdeen Proving Ground is 11.8 mi (19 ...

        $79 per night for 2 guests

        Inn at Haven Harbour

        Inn at Haven Harbour

        20880 Rock Hall Ave., Rock Hall
        Inn at Haven Harbour
          3.0 out of 5.0
           
           

          Situated on the waterfront, this bed & breakfast is 13.7 mi (22 km) from Washington College.

          $101 per night for 2 guests

          Mariners Motel

          Mariners Motel

          5681 South Hawthorne Avenue, Rock Hall
          Mariners Motel
            2.0 out of 5.0
             
             

            Situated near the bay, this motel is within a 15-minute walk of Rock Hall Harbor, The Mainstay, and Ferry Park. Garfield Center for the Arts at the Prince Theater ...

            $97 per night for 2 guests

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