Chestertown Vacation Packages
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Your Chestertown Vacation
There's no better way to embark on an adventure than with one of our vacation packages to Chestertown. The colonial history and cultural experiences are just two of the countless reasons to spend some time in this captivating city. Fill your free time with visits to Washington College, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater, some of the things you simply have to see during a trip to Chestertown. A couple of quick clicks is all it takes to put together a tailor-made Chestertown vacation on Expedia.
Top Chestertown Vacation Deals
Grand Hotel Ocean City Oceanfront
Reviewed on Feb 1, 2026
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
Polite and kind hotel manager
Reviewed on Jan 25, 2026
Historic Inns of Annapolis
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on Jan 31, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Very nice stay, staff was very understanding and breakfast was amazing. Room was clean and we had no problems.
Reviewed on Feb 4, 2026
Discover the most popular places to visit in Chestertown
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
