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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$139 per night from 29 May to 30 May
NZ$139
per night
29 May - 30 May
7.2/10 Good! (267 reviews)
"Sometimes, you don’t need a fancy place; just a clean place. That’s what this is. Maybe there weren’t the newest finishes, but we really appreciated having the extra pull-out couch and space in the room. It was perfect for traveling with my 3 teenagers."
Reviewed on 20 May 2024
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 29 May to 30 May
NZ$218
per night
29 May - 30 May
8.4/10 Very Good! (673 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$297 per night from 27 May to 28 May
NZ$297
per night
27 May - 28 May
8.8/10 Excellent! (1,609 reviews)
"Beautiful, central location, well appointed! Heating/cooling system is way loud."
Reviewed on 21 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.
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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.