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Choose from 1098 Chestertown Hotel Deals
Red Roof Inn & Suites Chestertown
"Hair dryer was broken and looked like it had been broken for awhile. Upon request staff provided one. Bed spread was clean but stained. No amenities at hotel not even list of restaurants close by. Hotel needs a complete renovation."
Reviewed on Oct 13, 2026
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
"Staff listened to my issues but didn't resolve them. Poor menu choices at breakfast and NO COFFEE on the last morning of the stay"
Reviewed on Oct 14, 2026
Historic Inns of Annapolis
"Great location."
Reviewed on Oct 14, 2026
Best Western Plus Hotel & Conference Center
"Oh my goodness thanks to all who made our stay so covenant and comfortable. I would definitely suggest a stay here if you are in the area. Kindest Regards"
Reviewed on Oct 13, 2026
Pendry Baltimore
"Great service teams and beautiful property! Also had a large group family style dinner in the Rec Pier Chop House and the food and service was superb! I’d definitely stay here again!"
Reviewed on Oct 13, 2026
Hampton Inn Baltimore/White Marsh
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Hampton Inn Baltimore/Glen Burnie
"The room was clean and comfortable. Staff friendly, especially the gentleman handling the breakfast. Unfortunately, I did not receive wake up calls in a timely manner. The first was 15 minute late and I do not know if I got a call the 2nd morning as it may have occurred after I left for breakfast. ..."
Reviewed on Oct 11, 2026
The Inn at Chesapeake Bay Beach Club
"We stayed at the Wilson’s Cove section next to the marina. Very nice accommodations. Restaurant was at the main hotel two blocks away. The staff was very friendly and the check-in staff at the main hotel helped me to get the room without having to pay extra since there was an Expedia reservation ..."
Reviewed on Oct 13, 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Find cheap hotels in Chestertown
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Frequently Asked Questions About Chestertown hotels
Where can I find the best last-minute travel deals?
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