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Chestertown Hotels

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Holiday Inn Express Hotel & Suites Chestertown Slideshow
#1 of 3 hotels in Chestertown
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Comfort Suites Slideshow
#2 of 3 hotels in Chestertown
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#3 of 3 hotels in Chestertown
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Still looking for a place to stay?
Chestertown has 12 B&Bs/inns with 672 reviews
#1 of 12 Chestertown B&B and Inns
#2 of 12 Chestertown B&B and Inns
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#3 of 12 Chestertown B&B and Inns
See all 12 Chestertown B&Bs/inns
Also consider hotels near Chestertown
See all hotels in or near Chestertown
Tallulah's on Main (Rock Hall)
7.0 miles from Chestertown
Swan Haven (Rock Hall)
7.2 miles from Chestertown
Mariners Motel (Rock Hall)
7.4 miles from Chestertown
17.7 miles from Chestertown
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17.8 miles from Chestertown
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Explore Chestertown, Maryland

Learn more about the best places to stay, eat, and play in Chestertown. Powered by first-hand advice from millions of travelers, TripAdvisor offers 1,781 reviews and 385 candid photos for 3 lodging options and 32 restaurants to help you plan the perfect trip to Chestertown.
Lemon Leaf Cafe
Where to eat Choose from 32 restaurants in Chestertown, such as Lemon Leaf Cafe. Here's what a recent traveler wrote about this restaurant: "The crabcakes are fabulous as is the cream of crab soup. There is a great pub next door which also has food and entertainment. Both places are an excellent addition to Chestertown. Brunch is served...". See all Chestertown restaurants.
Chestertown travel forum Need specific advice visiting Chestertown, Maryland? Visit the TripAdvisor Travel Forum for Chestertown and ask our Destination Experts and the travel community.