Popular Hotels in Chestertown 2025

• 

  John L Stam House, Chestertown

  HOTEL

  From $190.00

  0.8 mile from Center

  Get Details
• 

  Lodging at The Imperial

  From $158.00

  0.8 mile from Center

  Get Details
• 

  Brampton Bed and Breakfast Inn

  HOTEL

  From $189.00

  0.8 mile from Center

  Get Details
• 

  Driftwood Inn

  HOTEL

  From $65.00

  1.0 mile from Center

  Get Details
• 

  Holiday Inn Express Hotel & Suites Chestertown

  HOTEL

  From $84.00

  1.2 mile from Center

  Get Details
• 

  Great Oak Manor

  HOTEL

  From $199.00

  7.6 mile from Center

  Get Details
• 

  Inn at Mitchell House, Chestertown

  HOTEL

  From $125.00

  8.1 mile from Center

  Get Details