Chestertown Holidays
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is €102 per night from 30 Jun to 1 Jul
€102
30 Jun - 1 Jul
includes taxes & fees
8.6/10 Excellent! (918 reviews)
"I stayed here for 5 days and 4 nights housekeeping did not check my room once I never got new towels trash was never collected even when there was 2 adults and 3 kids in one room. Also The water pressure was not the best"
Reviewed on 1 Jun 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is €69 per night from 15 Jun to 16 Jun
€69
15 Jun - 16 Jun
includes taxes & fees
7.2/10 Good! (451 reviews)
"Towels might be too old? Must have been cleaned bath towels. But there are yellow stains. I did not feel like using them."
Reviewed on 2 Jun 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
The price is €130 per night from 3 Jun to 4 Jun
€130
3 Jun - 4 Jun
includes taxes & fees
7.8/10 Good! (83 reviews)
"There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. ..."
Reviewed on 28 May 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Garfield Center for the Arts at the Prince Theater
You can make plans for a show at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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