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 Rp1.696.297 per night from 23 Feb to 24 Feb
Rp1.696.297
Rp1.882.890 total
23 Feb - 24 Feb
includes taxes & fees
8.4/10 Very Good! (872 reviews)
Polite and kind hotel manager
Reviewed on 25 Jan 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,885 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 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 Rp1.088.964 per night from 17 Feb to 18 Feb
Rp1.088.964
Rp1.257.754 total
17 Feb - 18 Feb
includes taxes & fees
7/10 Good! (1,159 reviews)
Staff was nice room was clean...
Reviewed on 8 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
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.
