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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 147 Properties in Chestertown
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. ...

$97 per night for 2 guests

John L Stam House

John L Stam House

114 Washington Ave, Chestertown, MD
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 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

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
     
     

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

    Waterfront W/deepwater Pier Walking Distance to Downtown ChestertownGet Rates

    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 in the same area as Washington College. Regional attractions also include Rock Hall Harbor.

      Stunning Home on a 25-acre Private Woodland EstateGet 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 ...

        $179 per night for 2 guests

        Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay

        Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay

        Chestertown, MD
        Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake Bay
           
           

          Situated in a rural location, this vacation home is 11.7 mi (18.8 km) from Washington College.

          Sunview Cottage - Modern, Cozy Cottage for Relaxing Getaway on Chesapeake BayGet 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

            La Quinta Inn & Suites Edgewood / Aberdeen-South

            La Quinta Inn & Suites Edgewood / Aberdeen-South

            2112b Emmorton Park Rd, Edgewood, MD
            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 9.9 mi (15.9 km) from Ripken Stadium and 10.5 mi (16.9 km) from Harford Community College. Aberdeen Proving Ground and White ...

            $71 per night for 2 guests

            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. ...

            $57 per night for 2 guests

            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.

              $150 per night for 2 guests

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