
Chestertown Vacations
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Better together
Save up to ₩234,741 when you book a flight and hotel together*
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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 ₩154,480 per night from Aug 3 to Aug 4
₩154,480
₩171,473 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (778 reviews)
"We have stayed with this Comfort Inn, Chestertown, MD location in the past. Breakfast is handy, nearby grocery store and eateries are convenient. Farmers Market on Saturday and trendy Mom & Pop shops are close by. The staff are efficient and ice machines are abundant along with a washer/dryer (coins ..."
Reviewed on Jul 5, 2025

Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩94,065 per night from Jul 17 to Jul 18
₩94,065
₩104,412 total
Jul 17 - Jul 18
includes taxes & fees
7.2/10 Good! (370 reviews)
"Had a good time and enjoyed the quietness at the hotel."
Reviewed on Jul 3, 2025

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
The price is ₩181,943 per night from Jul 13 to Jul 14
₩181,943
₩201,957 total
Jul 13 - Jul 14
includes taxes & fees
7.8/10 Good! (53 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
Reviewed on Jun 22, 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.