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 €95 per night from 1 Feb to 2 Feb
€95
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (866 reviews)
Very nice
Reviewed on 14 Dec 2025
Pendry Baltimore
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is €358 per night from 29 Jan to 30 Jan
€358
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, and the staff was courteous and friendly.
Reviewed on 5 Jan 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 €63 per night from 18 Jan to 19 Jan
€63
18 Jan - 19 Jan
includes taxes & fees
7/10 Good! (1,125 reviews)
Cool
Reviewed on 7 Jan 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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