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Pick from 6 Chestertown Hotels with WiFi and compare room rates, reviews, and availability. Most hotels are fully refundable.

"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

"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

SAR 265 total

includes taxes & fees

23 Nov - 24 Nov

"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."

SAR 308 total

includes taxes & fees

1 Dec - 2 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 23 hours ago