Chestertown Travel Guide
Tourist Guide
Visit Chestertown
Comfort Inn & Suites Chestertown
"Parking clean room"
Reviewed on 5 Jun 2026
Red Roof Inn & Suites Chestertown
"Staff was pleasant and room was clean… but the shower/bathroom was awkward… shower curtain hung to allow no room to move around. Common areas were very dusty and vending machines not operable. Outside was very full of weeds. We booked online and didn’t expect these conditions."
Reviewed on 4 Jun 2026
The Lodge at Great Oak Landing
"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
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
"The room had issues in the toilet and also the ceiling broke and ended up ruining a pair of shoes from a leakage. The description of the pictures was not accurate to the room. I was supposed to have a suite and had one regular room with balcony."
Reviewed on 28 May 2026
Shore Point Cottages
"Amazing property. Quiet. Clean. Our family loved it."
Reviewed on 3 Jun 2026
Ocean Terrace Family Apartments
"Check in was a little confusing but overall it was a nice place to stay."
Reviewed on 2 Jun 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.
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.
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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
