Chestertown Holidays
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is €111 per night from 3 May to 4 May
€111
3 May - 4 May
includes taxes & fees
8.6/10 Excellent! (899 reviews)
The room was very clean but smelled as if someone had smoked in the room. Parlikg area was not well lighted and not welcoming.
Reviewed on 12 Apr 2026
Blue Heron Farm Waterfront Chalet
Chestertown MD
10/10 Exceptional! (2 reviews)
Location! Location!
Reviewed on 22 Jan 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is €105 per night from 19 Apr to 20 Apr
€105
19 Apr - 20 Apr
includes taxes & fees
7.8/10 Good! (77 reviews)
I was unaware that this hotel was a seasonal place to stay. When we arrived the place was a ghosttown. The two employees i
Reviewed on 8 Dec 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.
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