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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 ฿2,762 per night from 28 May to 29 May
฿2,762
per night
28 May - 29 May
7.2/10 Good! (261 reviews)
"Hotel was a hotel… hated the small toilets… if you go to wipe your hand will end up touching the water.. yuck! If you’re a man and have to poop…. hold your junk up!!!"
Reviewed on 13 May 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ฿4,472 per night from 29 May to 30 May
฿4,472
per night
29 May - 30 May
8.4/10 Very Good! (672 reviews)
"The onsite manager was very helpful. The staff was very nice."
Reviewed on 13 May 2024
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ฿5,801 per night from 28 May to 29 May
฿5,801
per night
28 May - 29 May
8.8/10 Excellent! (1,613 reviews)
"Beautiful hotel in the heart of the city. Everything was in walking distance. Nice staff. Loved the valet parking."
Reviewed on 13 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.