Chestertown Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is €103 per night from 28 Jun to 29 Jun
€103
28 Jun - 29 Jun
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! (450 reviews)
"The price was very good. The room was clean and spacious. There were a few maintenance issues. Several light bulbs were burned out, the hair dryer did not work, the closet door was off its track, and the Satellite TV was not working. The staff were helpful but unsuccessful in programming the TV. ..."
Reviewed on 1 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
