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Featured Chestertown Hotels with Air Conditioning
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chestertown MD
Located in Chestertown, this vacation home is on the waterfront, within a 10-minute drive of Chestertown Dog Park and Washington College.
Breakfast included
Kitchen
Driftwood Inn
609 Washington Avenue Chestertown MD
Free Cancellation
Reserve now, pay when you stay
With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 11 minutes by foot from Larrabee Arts Center.
Pet friendly
Parking included
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$114 nightly
The price is $126 total per night
$126 total
May 4 - May 5
Total with taxes and fees
Free Cancellation
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
160 Scheeler Rd Chestertown MD
$72 nightly
The price is $80 total per night
$80 total
May 10 - May 11
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 Larrabee Arts Center.
Pet friendly
Parking included
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.
Chestertown hotels essential information
Accommodation | 1,090 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $126 |
Popular hotels | Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, Driftwood Inn, Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown |
Most Recent Chestertown Hotel Reviews
Historic Inns of Annapolis
4 out of 5
Posted 4 hours ago
CheapTickets Verified Review
"Very good hotel but too expensive. Parking price was 50$, a rip off. We should have parked with an app. We didn’t expect the surprise in Annapolis. We pay that money in DC or NYC."
A verified traveler stayed at Historic Inns of Annapolis
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