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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
$64 nightly
The price is $70 total per night
$70 total
Aug 28 - Aug 29
Total with taxes and fees
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
Great Oak Manor
10568 Cliff Rd Chestertown MD
When you stay at Great Oak Manor in Chestertown, you'll be next to a golf course, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
On private beach
Breakfast included
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$107 nightly
The price is $119 total per night
$119 total
Sep 16 - Sep 17
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
$70 nightly
The price is $78 total per night
$78 total
Aug 30 - Aug 31
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 | 1,098 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $119 |
Popular hotels | Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town, Driftwood Inn, Great Oak Manor, Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown |
Most Recent Chestertown Hotel Reviews
Hampton Inn Baltimore/White Marsh
5 out of 5
Posted 11 hours ago
CheapTickets Verified Review
"Breakfast was good."
A verified traveler stayed at Hampton Inn Baltimore/White Marsh
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