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.
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...
Read more
2,562
travelers reviewed Chestertown
Be the first of your friends to travel here
See what your friends say about Chestertown
Log in with Facebook
Airports nearby (1)
Plan your day of travel
BWI
Balt.-Wash. Intl Airport
27.4 miles from Chestertown
Lowest airfare recently found by travelers like you
|
Local Weather
Powered by Weather Underground
77° 62°
August
70° 54°
September
59° 43°
October
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Sponsored by:
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Sponsored by:

    Are You a Chestertown Tourism Organization?

    Other Destinations
    Popular Maryland Destinations
    Aberdeen Hotels
    15 Hotels, 1,363 Reviews
    Annapolis Hotels
    21 Hotels, 8,744 Reviews
    Baltimore Hotels
    61 Hotels, 29,893 Reviews
    Cumberland
    3 Hotels, 732 Reviews
    Easton Hotels
    8 Hotels, 1,864 Reviews
    Frederick Hotels
    22 Hotels, 3,205 Reviews
    Ocean City Vacation Rentals
    1,218 Accommodations, 29,280 Reviews
    St. Michaels
    4 Hotels, 3,584 Reviews
    Interested in Chestertown?
    Get updates with the latest deals and traveler reviews every week.
    Sign up