An aerial view of a town with a river, buildings, and surrounding greenery.

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Tonight
23 Sep - 24 Sep
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24 Sep - 25 Sep
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25 Sep - 27 Sep
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2 Oct - 4 Oct
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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"It was great"
Peter 1-night trip
Posted 6 hours ago
Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"room was clean, and the breakfast was as expected. The only bad thing was that treadmill in the gym was out of service, which I found disappointing."
Steven 1-night trip
Posted 9 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."
John 2-night trip
Posted 10 hours ago
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"This Comfort Inn exceeded our expectations. The staff was very friendly and helpful, and the room was clean, comfortable, and updated. Easy and free parking. Breakfast offerings were generous and well presented, especially compared to other places on our trip. I would definitely stay here again. Thanks."
Teri 1-night trip
Posted 13 hours ago
Comfort Inn & Suites Chestertown
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."
Karen 3-night trip
Posted 1 day ago
Annapolis Waterfront Hotel, Autograph Collection
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Large rooms, refrigerator and microwave, good breakfast. Plenty of parking."
Mary 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"The room was clean and spacious"
Carla 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

8/10 Good
"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."
Jane 1-night trip
Posted 3 days ago
The Lodge at Great Oak Landing
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"I arrived early for check in and the desk clerk worked hard to get me in my room early before I had to leave for an event. She was very on top of things and friendly. I waited in the lobby while the room was being prepared and it was clean and comfortable. Later when I returned, we had a drink at the bar and the service was once again, great, with a friendly bartender (who remembered me from another stay). I looks as if the rooms have been refreshed since my last stay - clean and well designed. I slept like a log on the very comfortable bed! Basically, it was the least problematic hotel stay I may have ever had."
Barbara 1-night trip
Posted 3 days ago
Hilton Garden Inn Baltimore/White Marsh