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Blue Heron Farm Waterfront Chalet
Location! Location!
Reviewed on Jan 22, 2026
Pendry Baltimore
NA
Reviewed on Apr 20, 2026
Historic Inns of Annapolis
Unauthorized room charges after I checked out of over $100. Still unresolved.
Reviewed on Apr 21, 2026
Comfort Inn & Suites Chestertown
The whole experience was great
Reviewed on Apr 23, 2026
Hampton Inn Baltimore/Glen Burnie
Room were super clean and well kept. Excellent variety to choose from at breakfast, staff friendly and polite. Highly recommended.
Reviewed on Apr 20, 2026
The Lodge at Great Oak Landing
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, ...
Reviewed on Apr 23, 2026
Best Western Plus Hotel & Conference Center
Eggs were the bagged kind. Bland. Lot of pot smell by our room, very unhealthy. People hanging outside of their rooms and loud. Rugs need cleaning or replacement and bathrooms need some renovation.
Reviewed on Apr 12, 2026
Hilton Garden Inn Baltimore/White Marsh
My guess and I were pretty pleased
Reviewed on Apr 23, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
The elevator was broken. They did not have enough wash rags & towels. They told my adults children to come back in the morning and ask for amenities. Instead of going out their way to provide us with them. The hallway smelled like smoke . The telephone in the room was broke. The back door was broke ...
Reviewed on Apr 21, 2026
Driftwood Inn
5 Star Hotels
Chestertown Hotel & Travel Guide\n
For those adventurers that find themselves roaming around in Eastern Chesapeake Shore and decide on spending some time in Chestertown, there are a select number of hotels. With 5 accommodation options on Travelocity within a 6-mile (10-kilometer) sweep of Chestertown, it'll be easy finding something that ticks all your boxes.
Chestertown's downtown region is within strolling distance of comfortable hotels including Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.
Chestertown features just a handful of no-frills hotels; you'll find the Driftwood Inn located 2 miles (3 kilometers) from the heart of town.
Check out the Historic Kent Manor Inn and also the Hilton Garden Inn Kent Island. The Historic Kent Manor Inn is located 20 miles (32 kilometers) away from the center of Chestertown. The Hilton Garden Inn Kent Island, is located 18 miles (29 kilometers) away. Some other accommodation options include the Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island.
Keen on exploring more of the coastal plains and wetlands that this area features? How about you have a few nights in some of the other places in Eastern Maryland? No matter if you get involved with commonplace local activities, like, for example, ice fishing, hiking and shore fishing, or desire to zigzag across the region to photograph the many attractions, you will have no trouble booking comfortable Travelocity-listed hotels close to here.
Looking for more things to do? You could spend a few hours seeing Chesapeake Bay Maritime Museum and St. Michaels Museum, which you'll find in St. Michaels, 30 miles (47 kilometers) south of Chestertown. If you head to St. Michaels, check out the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. For another option, head to Rock Hall, 10 miles (16 kilometers) to the southwest of Chestertown, where you can pick from the Mariners Motel and Inn at Osprey Point. When you visit Rock Hall, be sure to venture to the Mainstay and Rock Hall Harbor.
Baltimore Washington International Thurgood Marshall Airport is 30 miles (50 kilometers) away from the center of Chestertown. Enlightened visitors who need to find a room nearby can easily secure a convenient option in the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.
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