Best Hotels in Chestertown, MD

Here’s the America’s Best Online list of the best Hotels in Chestertown, MD. Imperial Hotel got the current top hotel ranking for Chestertown. Closely following #1 are Inn at Mitchell House, Comfort Suites Chestertown, White Swan Tavern and Driftwood Inn. After reading the top ten hotels in Chestertown (and the honorable mentions including Parker House) be sure to check out the Maryland Hotels nearby in cities such as Centreville, Queenstown, Edgewood, Grasonville and Stevensville.

Top 10 Hotels in Chestertown, MD

  1. Imperial Hotel
    208 High St, Chestertown, MD 21620
     • 800-295-0014

  2. Inn at Mitchell House
    8796 Maryland Pkwy, Chestertown, MD 21620
     • 410-778-6500

  3. Comfort Suites Chestertown
    160 Scheeler Rd, Chestertown, MD 21620
     • 410-810-0555

  4. White Swan Tavern
    231 High St, Chestertown, MD 21620
     • 410-/-778-2300
    Unrated

  5. Driftwood Inn
    609 Washington Avenue, Chestertown, MD 21620
     • 410-778-3200
    Unrated

  6. April Inn
    407 E Campus Ave, Chestertown, MD 21620
     • 410-778-3603
    Unrated

  7. Carriage House Inn
    5877 Coleman Road, Chestertown, MD 21620

    Unrated

  8. Gracious Inns of The Chesapeake
    110 Wilton Rd, Chestertown, MD 21620
     • 410-778-3970
    Unrated

  9. Great Oak Landing Lodge
    22170 Great Oak Landing Rd, Chestertown, MD 21620
     • 410-778-5007
    Unrated

  10. Holiday Inn Exp Stes Chestertw
    150 Scheeler Road, Chestertown, MD 21620
     • 800-4654329
    Unrated

Honorable Mentions for Hotels in Chestertown

  • Parker House
    108 Spring Ave, Chestertown, MD 21620
     • 410-778-9041

Top Hotels Near Chestertown

  • Hillside Motel (Centreville, MD)
    11.6 miles from Chestertown
  • Pintail Point (Queenstown, MD)
    15.9 miles from Chestertown
  • Hampton Inn Baltimore/Edgewood (Edgewood, MD)
    18.9 miles from Chestertown
  • Hilton Garden Inn Kent Island (Grasonville, MD)
    19 miles from Chestertown
  • Historic Kent Manor Inn (Stevensville, MD)
    20.6 miles from Chestertown