Chestertown Holidays
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Chestertown Holiday
Our pick of the best Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundable
The price is NZ$225 per night from 26 Apr to 27 Apr
NZ$225
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (895 reviews)
The breakfast was as one would expect. Nothing unusual. I wish these hotels wouldn’t use so much plastic. Everything was clean. Chestertown is wonderful. Good restaurants. Much to see. The hotel is not fancy. Just a reliable place to be. Nothing unexpected. All good.
Reviewed on 3 Apr 2026
Blue Heron Farm Waterfront Chalet
Chestertown MD
10/10 Exceptional! (2 reviews)
Location! Location!
Reviewed on 22 Jan 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$319 per night from 19 Apr to 20 Apr
NZ$319
19 Apr - 20 Apr
includes taxes & fees
9/10 Wonderful! (1,868 reviews)
Great historic building… felt like home away from home.
Reviewed on 4 Apr 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.
Discover the most popular places to visit in Chestertown
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.
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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.
