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Pick from 5 Chestertown Adventure Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "

SAR 442 total

includes taxes & fees

15 Dec - 16 Dec

Find out more about Chestertown

Recent reviews of Chestertown hotels

5/5 Excellent

"I love staying at this property. It is within walking distance of everything, especially Main Street and the Naval Academy. The valet service is excellent, and the staff is always friendly and helpful. The rooms are always clean and comfortable."

A verified traveler stayed at Historic Inns of Annapolis

Posted 1 day ago