Chestertown Holidays
Photo by Patricia Knorr
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Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
The price is €77 per night from 21 Oct to 22 Oct
€77
21 Oct - 22 Oct
includes taxes & fees
7.2/10 Good! (402 reviews)
"Well received by front desk attendant. Clean room!"
Reviewed on 10 Oct 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
The price is €98 per night from 26 Oct to 27 Oct
€98
26 Oct - 27 Oct
includes taxes & fees
8.4/10 Very Good! (826 reviews)
"Nice hotel"
Reviewed on 29 Sept 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is €130 per night from 23 Oct to 24 Oct
€130
23 Oct - 24 Oct
includes taxes & fees
7.8/10 Good! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
Reviewed on 5 Sept 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.
