Hotels with Restaurants in Chestertown
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Featured Chestertown Hotels with Restaurants

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
$114 nightly
The price is $126 total per night
$126 total
Jun 7 - Jun 8
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included

Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $80 total per night
$80 total
May 17 - May 18
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a TV in a common area, and a vending machine.
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 | 1,092 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $126 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown |
Recent Hotels with Restaurants Reviews

Historic Inns of Annapolis
5/5 Excellent
"The only thing that was not 100% amazing was the toilet in our room was small and short and so was the shower head. I am only 5’4” so there is no way my husband would have been able to use either at 6’2”…. Other than that it was such an incredible historic place with all the grandeur and old wonderful charm!"
A verified traveler stayed at Historic Inns of Annapolis
Posted 7 hours ago
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