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Top hotels in Chestertown
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿3,858 per night from 12 May to 13 May
฿3,858
per night
12 May - 13 May
7.2/10 Good! (261 reviews)
"This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'."
Reviewed on 13 Apr 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿4,498 per night from 16 May to 17 May
฿4,498
per night
16 May - 17 May
8.4/10 Very Good! (669 reviews)
"Everything was great"
Reviewed on 5 May 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ฿6,254 per night from 28 May to 29 May
฿6,254
per night
28 May - 29 May
8.8/10 Excellent! (1,609 reviews)
"Very nice location."
Reviewed on 8 May 2024
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.
Frequently asked questions
Popular places to visit
Washington College
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
River Arts Chestertown
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.