Compare Hotels with Restaurants in Chestertown

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Featured Chestertown Hotels with Restaurants

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
$107 nightly
The price is $119 total per night
$119 total
Jan 6 - Jan 7, 2026
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 13 - Dec 14
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
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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
1,085 hotels
Lowest Price
$80
Highest Price
$119
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown

Most Recent Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

5 out of 5
Posted 1 day ago
CheapTickets Verified Review
"The room was exll"
A verified traveler stayed at Hilton Garden Inn Baltimore/White Marsh
Hilton Garden Inn Baltimore/White Marsh

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