We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chestertown Vacations

With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British... more
With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Sponsor:
Chestertown
Chestertown (SkiScuba, Mar 2009)
Recommended for you...
The Inn at Mitchell House 5.0 of 5 stars 42 reviews Great Oak Manor Inn 5.0 of 5 stars 131 reviews Simply Bed and Bread 5.0 of 5 stars 101 reviews Comfort Suites 4.0 of 5 stars 72 reviews
Show Prices ABS:HotelCheckRates-d93725?&src=Tourism&fromServlet=Tourism&Action=QC_TourismRFYBelowFold
View all 3 hotels in Chestertown, ranked by popularity

Are You a Chestertown Tourism Organization?

  • Visit our page for Chestertown tourism organizations
  • Add Photo
  • Add Video
Other Destinations
Popular Maryland Destinations
Aberdeen Hotels
14 hotels, 540 Reviews
Annapolis Hotels
62 hotels, 4,581 Reviews
Baltimore Hotels
107 hotels, 16,464 Reviews
Cumberland
8 hotels, 372 Reviews
Easton Hotels
22 hotels, 862 Reviews
Frederick Hotels
34 hotels, 1,389 Reviews
Ocean City Vacation Rentals
711 hotels, 16,000 Reviews
St. Michaels
29 hotels, 2,103 Reviews