Chestertown Holidays
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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 €95 per night from 22 Mar to 23 Mar
€95
22 Mar - 23 Mar
includes taxes & fees
8.6/10 Excellent! (879 reviews)
I reserved a suite for two nights on 12/26/25. Almost 2 months in advance. When I arrived the check-in girl said that she downgraded my room to a double because they were overbooked and since I only two people in my group she gave my suite to a party with 4 people because they needed more room than ...
Reviewed on 17 Feb 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is €70 per night from 16 Mar to 17 Mar
€70
16 Mar - 17 Mar
includes taxes & fees
7/10 Good! (1,172 reviews)
I had a one night stay at this property, and I came home with bedbugs and bedbug bites all over my body… I actually had to seek medical attention. The condition of the hotel is very poor and disgusting. I believe it serves as a hotel and a homeless shelter in One. Please be aware of this ...
Reviewed on 3 Mar 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,877 reviews)
Such a cool place to stay! Water pressure wasn’t great but it’s a very old building.
Reviewed on 26 Feb 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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