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
$103 nightly
The price is $115 total per night
$115 total
Jul 12 - Jul 13
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.

Driftwood Inn
609 Washington Avenue Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$64 nightly
The price is $70 total per night
$70 total
Jun 22 - Jun 23
Total with taxes and fees
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.

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
Jun 25 - Jun 26
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 TV in a common area.
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 | 1,087 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $115 |
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
"We had an amazing stay at the Historic Inns of Annapolis and would absolutely stay here again. From the moment we arrived, the valet staff was incredible. Everyone was warm, welcoming, and genuinely helpful. One thing that really stood out was that they allowed us to keep our car with valet service until 2:00 p.m. on the day we checked out so we could spend a little more time exploring Annapolis before heading to the airport. That extra accommodation made a huge difference and was very much appreciated. The grounds and buildings are beautiful, and the historic charm throughout the property is amazing. Our room was comfortable, clean, and exactly what we hoped for in a historic inn. The only downside was the bathroom. The shower/tub area was very small. I'm not even 5 feet tall and barely 100 pounds, and it felt pretty cramped even for me. That said, it certainly wasn't enough to take away from an otherwise excellent stay. The bar was fantastic, and the bartender was awesome. I wish I could remember his name because he made the best chocolate martini I've ever had. While chatting with us, he even gave us a little tour of some of the downstairs historic lobby areas, which was such a nice touch and made us appreciate the property's history even more. Overall, everything was wonderful. Beautiful property, great staff, excellent service, and a perfect location. We'd absolutely stay here again and do it all over in a heartbeat."
A verified traveler stayed at Historic Inns of Annapolis
Posted 4 hours ago


