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Chestertown Holidays
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Photo by Assya A
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Our pick of the best Chestertown Hotel Deals
![Red Roof Inn & Suites Chestertown](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/0d84b7e3_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$146 per night from 26 Jun to 27 Jun
NZ$146
per night
26 Jun - 27 Jun
7.2/10 Good! (280 reviews)
"Not exceptional, but clean."
Reviewed on 16 Jun. 2024
![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/d4e0c3f2_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$231 per night from 24 Jun to 25 Jun
NZ$231
per night
24 Jun - 25 Jun
8.4/10 Very Good! (671 reviews)
"It was great"
Reviewed on 3 Jun. 2024
![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$254 per night from 7 Jul to 8 Jul
NZ$254
per night
7 Jul - 8 Jul
8.8/10 Excellent! (1,607 reviews)
"Great location. Clean rooms."
Reviewed on 18 Jun. 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.