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Top 10 Hotels in Chestertown

See all 129 Properties in Chestertown
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
John L Stam House
  • Free Cancellation
  • Reserve now, pay when you stay
3.0 out of 5.0
 
 

Situated in Chestertown, this bed & breakfast is 13.3 mi (21.5 km) from The Mainstay and within 32 mi (52 km) of Queenstown Harbor Golf Club and Frog Hollow ...

$190 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. Regional attractions also include Rock Hall 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
    Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
       
       

      Situated in the city center, this historic vacation home is close to Washington College. Regional attractions also include The Mainstay and Rock Hall ...

      Waterfront W/deepwater Pier Walking Distance to Downtown ChestertownGet Rates

      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 13.1 mi (21.1 km) from The Mainstay and within 32 mi (52 km) of Queenstown Harbor Golf Club and Frog Hollow Golf ...

      $89 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 13 mi (20.9 km) from The Mainstay and within 32 mi (52 km) of Queenstown Harbor Golf Club and Frog Hollow Golf Club.

      $57 per night for 2 guests

      Chester River Waterfront, Magnificent Views, Dock, Beach

      Chester River Waterfront, Magnificent Views, Dock, Beach

      , Chestertown
      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 32 mi (52 km) of The Mainstay and Frog Hollow Golf ...

        Chester River Waterfront, Magnificent Views, Dock, BeachGet Rates

        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
        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 32 mi (52 km) of Queenstown Premium Outlets and ...

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

          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 12 mi (19.3 km) from The Mainstay.

            $179 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 Ripken Stadium, Harford Community College, and Aberdeen Proving Ground. Boordy Vineyards and Harford ...

            $71 per night for 2 guests

            Inn at Mitchell House

            Inn at Mitchell House

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

              Situated near the beach, this bed & breakfast is 6.7 mi (10.7 km) from The Mainstay.

              $150 per night for 2 guests

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