Find hotels near Chestertown Historic District, Chestertown from $160

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Compare 2,126 hotels close to Chestertown Historic District with room rates, reviews, and availability. Most hotels are fully refundable.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
$144 nightly
The price is $160
Nov 2 - Nov 3
Total with taxes and fees
Mariners Motel

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (70)
"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!!"
$151 nightly
The price is $168
Oct 5 - Oct 6
Total with taxes and fees
The Lodge at Great Oak Landing
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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