Chestertown Holidays
Photo by Patricia Knorr
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is €98 per night from 4 Dec to 5 Dec
€98
4 Dec - 5 Dec
includes taxes & fees
8.4/10 Very Good! (857 reviews)
Excellent hotel. Will stay there anytime I travel to the area.
Reviewed on 26 Nov 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is €69 per night from 30 Dec to 31 Dec
€69
30 Dec - 31 Dec
includes taxes & fees
7.2/10 Good! (417 reviews)
room was clean but the shower curtain was in tatters. multiple rings torn off
Reviewed on 20 Nov 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is €98 per night from 30 Dec to 31 Dec
€98
30 Dec - 31 Dec
includes taxes & fees
7.8/10 Good! (76 reviews)
Beautiful view
Reviewed on 8 Nov 2025
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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
