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Tonight Apr 24 - Apr 25
This weekend Apr 26 - Apr 28
Next weekend May 3 - May 5

Top 10 Hotels in Chestertown

See all 146 Properties in Chestertown

Estimated price for 1 night/2 adults

Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown, MD
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 within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. ...

$90 per night for 2 guests

May 6 - May 7
John L Stam House

John L Stam House

114 Washington Ave, Chestertown, MD
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 within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf ...

    $190 per night for 2 guests

    Apr 29 - Apr 30
    Stunning Home on a 25-acre Private Woodland Estate

    Stunning Home on a 25-acre Private Woodland Estate

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

      Situated in Chestertown, this historic vacation home is 3.9 mi (6.3 km) from Washington College and 9.1 mi (14.7 km) from Rock Hall Harbor. Queenstown Harbor ...

      Stunning Home on a 25-acre Private Woodland EstateGet Rates

      Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown

      Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown

      Chestertown, MD
      Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
         
         

        Located in the heart of Chestertown, this historic vacation home is 1.5 mi (2.4 km) from Washington College and within 32 mi (52 km) of Rock Hall Harbor and ...

        Waterfront W/deepwater Pier Walking Distance to Downtown ChestertownGet Rates

        Driftwood Inn

        Driftwood Inn

        609 Washington Avenue, Chestertown, MD
        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 within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. ...

        $59 per night for 2 guests

        Apr 25 - Apr 26
        Chester River Waterfront, Magnificent Views, Dock, Beach

        Chester River Waterfront, Magnificent Views, Dock, Beach

        Chestertown, MD
        Chester River Waterfront, Magnificent Views, Dock, Beach
           
           

          Situated in Chestertown, this historic vacation home is 2.9 mi (4.7 km) from Washington College and within 25 mi (40 km) of Rock Hall Harbor and Mount Harmon ...

          Chester River Waterfront, Magnificent Views, Dock, BeachGet Rates

          Great Oak Manor

          Great Oak Manor

          10568 Cliff Rd, Chestertown, MD
          Great Oak Manor
            3.5 out of 5.0
             
             

            Nestled on the beach, this Chestertown bed & breakfast is next to a golf course, 9.1 mi (14.6 km) from Washington College, and 12.5 mi (20.2 km) from Rock Hall ...

            $199 per night for 2 guests

            Apr 24 - Apr 25
            Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

            Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town

            Chestertown, MD
            Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From Town
               
               

              Located in Chestertown, this family-friendly property is 2.3 mi (3.8 km) from Washington College, and within 16 mi (25 km) of The Mainstay and Rock Hall Harbor. ...

              Waterfront 3 Br/1 ba Country Cottage w/ Gameroomdeep Water,dock, 2 mi From TownGet Rates

              Quality Suites

              Quality Suites

              160 Scheeler Rd, Chestertown, MD
              Quality Suites
                2.5 out of 5.0
                 
                 

                Situated in Chestertown, this hotel is 0.6 mi (1 km) from Washington College and within 32 mi (52 km) of Rock Hall Harbor and Queenstown Harbor Golf Club. Queenstown ...

                Quality SuitesGet Rates

                Inn at Mitchell House

                Inn at Mitchell House

                8796 Maryland Pkwy, Chestertown, MD
                Inn at Mitchell House
                  3.0 out of 5.0
                   
                   

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

                  $125 per night for 2 guests

                  May 20 - May 21
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