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Our pick of the best Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$154 per night from 30 May to 31 May
NZ$154
per night
30 May - 31 May
7.2/10 Good! (270 reviews)
"Property was OK, would stay again"
Reviewed on 26 May 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$223 per night from 30 May to 31 May
NZ$223
per night
30 May - 31 May
8.4/10 Very Good! (676 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 NZ$283 per night from 16 Jun to 17 Jun
NZ$283
per night
16 Jun - 17 Jun
8.8/10 Excellent! (1,614 reviews)
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance."
Reviewed on 27 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
Discover the most popular places to visit in Chestertown
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.