Hotels & places to stay in Chestertown
26 places to stay in Chestertown, MD — ranked by guest rating and popularity.
Where to stay in Chestertown
There are 8 places to stay in Chestertown on Where to Rest, mostly hotels. Among the highest-rated stays are Brampton 1860, Comfort Inn & Suites Chestertown and Driftwood Inn.
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The numbers
26 places to stay · 6 guest-rated · average 4.0★ — including 1 five-star hotels
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HotelDaylight hours in Chestertown
Daylight hours (15th of each month).
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Staying in Chestertown — FAQs
How many places to stay are there in Chestertown?
There are 26 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 Brampton Bed and Breakfast Inn, Brittland Estates, Comfort Inn & Suites. See our ranked list of the best places to stay in Chestertown.
Are there pet-friendly places to stay in Chestertown?
3 places to stay in Chestertown welcome pets. Use the "Pet friendly" filter to see them all.