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 Rp1.686.724 per night from 25 Jan to 26 Jan
Rp1.686.724
Rp1.872.265 total
25 Jan - 26 Jan 2026
includes taxes & fees
8.4/10 Very Good! (861 reviews)
Very nice
Reviewed on 14 Dec 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is Rp1.205.352 per night from 2 Jan to 3 Jan
Rp1.205.352
Rp1.337.941 total
2 Jan - 3 Jan 2026
includes taxes & fees
7.2/10 Good! (421 reviews)
Very clean. Pets allowed.
Reviewed on 14 Dec 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,904 reviews)
Great customer service!
Reviewed on 21 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
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
Crumpton Auction
Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
