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Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
"Great location. Clean rooms."
Reviewed on Aug 10, 2026
Red Roof Inn & Suites Chestertown
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
Reviewed on Aug 10, 2026
Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection
"When we checked in, on a humid 95 degree day, the staff lied to us and said that they were making a small adjustment and a/c was down but would be back up in an hour. Took our money, then, when we got to our room, a letter by the door said the a/c would not be fixed that day or night. Then, we found ..."
Reviewed on Aug 9, 2026
Pendry Baltimore
Best Western Plus Hotel & Conference Center
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
"The room wasn’t anything special.. The bed sheet was very worn.. the carpet felt sticky the tv remote felt gross.. The Tv barely worked and was off line during my entire stay. the staff looked like they didn’t want to be bothered especially the lady that check us out didn’t even look at us and just ..."
Reviewed on Aug 11, 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Hyatt Place Kent Narrows & Marina
Hampton Inn & Suites Edgewood/Aberdeen-South
"Traveled with kids. Excellent amenities and clean rooms. Staff friendly and helpful! Location was great for highway access into Baltimore."
Reviewed on Aug 11, 2026
Hampton Inn Baltimore/White Marsh
"Needs more Staffing at the front desk."
Reviewed on Aug 11, 2026
Find cheap hotels in Chestertown
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Choosing the right hotel in Maryland has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Chestertown’s 1,100 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $67. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Chestertown hotel deals at the last minute.
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Frequently Asked Questions About Chestertown hotels
Where can I find the best last-minute travel deals?
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How many hotels are there in Chestertown?
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