Hotels & places to stay in Chestertown
8 places to stay in Chestertown, MD — ranked by guest rating and popularity.
About Chestertown:Population 5,0934 m elevationAmerica/New York time
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Showing 8 of 8
Bed & BreakfastThe Guesthouse Bed and Breakfast
114 Washington Ave, Chestertown, MD 21620
★ 5.0 (22)
HotelBrampton 1860★★★★★
25227 Chestertown Rd, Chestertown, MD 21620
★ 4.9 (606)
HotelWhite Swan Tavern
★ 4.9 (61)
HotelComfort Inn & Suites Chestertown
150 Scheeler Rd, Chestertown, MD 21620
★ 3.6 (156)
HotelRed Roof Inn★★★
160 Scheeler Road, Chestertown
★ 3.1 (104)
MotelDriftwood Inn★★
609 Washington Avenue, Chestertown
★ 2.4 (119)
Hotel
Comfort Inn & Suites
150 Scheeler Road, Chestertown
HotelInn at Perry’s Cabin
Dorchester House, Chestertown, MD 21620
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Staying in Chestertown — FAQs
How many places to stay are there in Chestertown?
There are 8 places to stay listed in Chestertown on Where to Rest — hotels, motels, hostels, apartments and more, with photos, guest ratings, amenities and booking links.
Where is the best place to stay in Chestertown?
Top-rated stays in Chestertown include Comfort Inn & Suites, Inn at Perry’s Cabin, Brampton 1860. See our ranked list of the best places to stay in Chestertown.