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Featured Chestertown Hotels with Air Conditioning

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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.
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.
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 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.
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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
$70
Highest Price
$113
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

Pendry Baltimore

Pendry Baltimore

5 out of 5
Posted 4 days ago
CheapTickets Verified Review
"Beautiful hotel. 5 out of 5"
A verified traveler stayed at Pendry Baltimore
Pendry Baltimore

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