Hotels with WiFi in Chestertown
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Featured Chestertown Hotels with WiFi

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $112 total per night
$112 total
Feb 25 - Feb 26
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

Driftwood Inn
609 Washington Avenue Chestertown MD
At Driftwood Inn, guests have access to free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Pet friendly
Parking 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
Feb 5 - Feb 6
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 vending machine, and a fireplace in the lobby.
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 | 1,081 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $112 |
Popular hotels | Comfort Inn & Suites Chestertown, Driftwood Inn, Red Roof Inn & Suites Chestertown |
Recent Hotels with WiFi Reviews

Historic Inns of Annapolis
5/5 Excellent
"Due to the history and age of this beautiful bldg, we expected relatively dated rooms. Much to our surprise, the room was clean, spacious and modern. This is one of the most pleasurable experiences I ever have had not only in Annapolis, but anywhere. "
A verified traveler stayed at Historic Inns of Annapolis
Posted 2 days ago


