Chestertown Trip
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
The price is ₹10,222 per night from 2 Jul to 3 Jul
₹10,222
₹11,346 total
2 Jul - 3 Jul
includes taxes & fees
8.6/10 Excellent! (921 reviews)
"Parking clean room"
Reviewed on 5 Jun 2026
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
The price is ₹6,865 per night from 17 Jun to 18 Jun
₹6,865
₹7,620 total
17 Jun - 18 Jun
includes taxes & fees
7.2/10 Good! (455 reviews)
"The staff,( if you want to call them that)don't greet you when you walk in to register, I had to initiate the conversation. The elevator floor was filthy nasty and it creaked and groaned. We got off of the elevator on our floor and was greeted by Marijuana smoke and smell. I went back down to inform ..."
Reviewed on 7 Jun 2026
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is ₹12,615 per night from 17 Jun to 18 Jun
₹12,615
₹14,423 total
17 Jun - 18 Jun
includes taxes & fees
7.8/10 Good! (86 reviews)
"This property is situated in a beautiful marina with excellent facilities. Guests staying at the Lodge can also enjoy complimentary golf, which was a great bonus. We thoroughly enjoyed our stay and would happily return. The only drawback was that the Wi-Fi service was somewhat inconsistent."
Reviewed on 6 Jun 2026
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.
Popular places to visit
Historical Society of Kent County Maryland
You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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