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Featured Chestertown Hotels with Pools

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
$102 nightly
The price is $113 total per night
$113 total
Dec 25 - Dec 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland.
Pool
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
$72 nightly
The price is $80 total per night
$80 total
Dec 11 - Dec 12
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Chestertown Dog Park.
Pet friendly
Parking included
Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue Chestertown MD
$64 nightly
The price is $70 total per night
$70 total
Dec 24 - Dec 25
Total with taxes and fees
With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 12 minutes by foot from Rolling Road Park.
Pet friendly
Parking included
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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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Chestertown hotels essential information

Accommodation
1,086 hotels
Lowest Price
$70
Highest Price
$113
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Driftwood Inn

Most Recent Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Over all the room was everything we expected and more 😊😊 will definitely be booking again."
A verified traveler stayed at Best Western Plus Hotel & Conference Center
Best Western Plus Hotel & Conference Center

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