Chestertown
Travel Guide
Visit Chestertown
Comfort Inn & Suites Chestertown
"my favorite place to stay when going to Chestertown. Recommend this hotel vs any other in the area"
Reviewed on 28 May 2026
Red Roof Inn & Suites Chestertown
"The staff at the front is very rude. Everytime I would go to the front I would have to say hello multiple times for somebody to come to the front to assist me. There was a guy on night shift with black glasses, would always say Jesus Christ or would mumble under his breath because it seemed like ..."
Reviewed on 29 May 2026
The Lodge at Great Oak Landing
"There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. ..."
Reviewed on 28 May 2026
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
"Lovely cabin in the woods! Nice water access and quiet surrounding."
Reviewed on 18 May 2026
Chesapeake Houseboat Getaway on Kent Island, Maryland
"Such a cool experience"
Reviewed on 24 May 2026
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
"Love this property and this is the second time I have stayed here. You can't get closer to gate 1 of the Naval Academy, and a short walk to downtown. The place smells wonderful when you enter, very clean and fresh. Great bed, linens and towels. The courtyard in the back is a great place to relax ..."
Reviewed on 22 Apr 2026
Popular places to visit
Washington College
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
River Arts Chestertown
Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.
Chestertown Historic District
Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.
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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Chestertown Dog Park
Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
