Chestertown Trip
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Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₹9,200 per night from 8 Mar to 9 Mar
₹9,200
₹10,212 total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (879 reviews)
I reserved a suite for two nights on 12/26/25. Almost 2 months in advance. When I arrived the check-in girl said that she downgraded my room to a double because they were overbooked and since I only two people in my group she gave my suite to a party with 4 people because they needed more room than ...
Reviewed on 17 Feb 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Fully refundableReserve now, pay when you stay
The price is ₹6,476 per night from 1 Mar to 2 Mar
₹6,476
₹7,479 total
1 Mar - 2 Mar
includes taxes & fees
7/10 Good! (1,171 reviews)
This was a run down, smelly property with questionable people staying at the same time. The main issues: - The room, which was supposed to be nonsmoking, reeked of cigarettes and was almost impossible to sleep in - The bathroom door was dirty, covered with red stains - The sink was cracked - The ...
Reviewed on 25 Feb 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,890 reviews)
The room really showed its age. The entire room was tilted.... so much so that a bottle rolled on the floor from the left to the right without any push. The bed was likewise tilted and really difficult to sleep comfortably. The elevator was out of order, and there were older guests on the 3rd floor ...
Reviewed on 23 Feb 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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