Chestertown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
"I called the central reservation desk to extend my stay at 08000 the morning of check-in. They verified the reservation under the current ID was extended. When I confirmed this with the front desk, she said they were no rooms available. There was no discussion and she and the next clerk gave no explanation. ..."
Reviewed on May 19, 2026
Red Roof Inn & Suites Chestertown
"This hotel is in need of repair. The pull out sofa had more rips and tears than what should ever be seen. Way over priced for what you get"
Reviewed on May 19, 2026
The Lodge at Great Oak Landing
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again"
Reviewed on May 18, 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.
