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 refundable
The price is ￥17,172 per night from Jul 8 to Jul 9
￥17,172
￥19,060 total
Jul 8 - Jul 9
includes taxes & fees
8.6/10 Excellent! (921 reviews)
"Parking clean room"
Reviewed on Jun 5, 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ￥11,519 per night from Jun 30 to Jul 1
￥11,519
￥12,786 total
Jun 30 - Jul 1
includes taxes & fees
7.2/10 Good! (455 reviews)
"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform ..."
Reviewed on Jun 7, 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is ￥21,169 per night from Jun 17 to Jun 18
￥21,169
￥24,204 total
Jun 17 - Jun 18
includes taxes & fees
7.8/10 Good! (87 reviews)
"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest ..."
Reviewed on Jun 10, 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.
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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.
