Chestertown Vacations
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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
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩113,409 per night from Oct 6 to Oct 7
₩113,409
₩125,884 total
Oct 6 - Oct 7
includes taxes & fees
7.2/10 Good! (396 reviews)
"Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service."
Reviewed on Sep 1, 2025
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩163,813 per night from Oct 30 to Oct 31
₩163,813
₩181,832 total
Oct 30 - Oct 31
includes taxes & fees
8.4/10 Very Good! (820 reviews)
Clean and quiet
"Nicely appointed with plenty of towels, and easy to operate TV and A/C."
Reviewed on Sep 23, 2025
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is ₩185,234 per night from Oct 1 to Oct 2
₩185,234
₩205,611 total
Oct 1 - Oct 2
includes taxes & fees
7.8/10 Good! (70 reviews)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
Reviewed on Sep 5, 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
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.
