Chestertown Vacations
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Find the Best Chestertown Vacation Packages
Chestertown Hotel Deals
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₩139,508 per night from Jan 4 to Jan 5
₩139,508
₩154,853 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.4/10 Very Good! (861 reviews)
Very nice
Reviewed on Dec 14, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₩102,937 per night from Jan 6 to Jan 7
₩102,937
₩114,261 total
Jan 6 - Jan 7, 2026
includes taxes & fees
7.2/10 Good! (422 reviews)
Very clean. Pets allowed.
Reviewed on Dec 14, 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,902 reviews)
Excellent location! Courteous staff. Clean rooms. Great stay!
Reviewed on Dec 30, 2025
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
Crumpton Auction
4.5/5(3 reviews)
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.
