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The Lodge at Great Oak Landing
"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and ..."
Reviewed on Aug 30, 2026
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Pendry Baltimore
Hampton Inn Baltimore/Glen Burnie
"Only one elevator working and it was the slowest elevator ever, especially since there is only 5 floors! The lobby is bright and welcoming, but the room, while clean, had dark furniture and dark carpeting and are generally just not very bright and cheery. We have stayed here before and had no issues ..."
Reviewed on Aug 31, 2026
Best Western Plus Hotel & Conference Center
"My visit was great I have no complaints also the complimentary breakfast was really good alot of options and great food choices in also liked the fact that check out time was at 12 noon I'll definitely stay next time I visit the area thank you"
Reviewed on Sep 1, 2026
Annapolis Waterfront Hotel, Autograph Collection
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn Baltimore/White Marsh
"Breakfast was great the bed was amazing and the area was near everything"
Reviewed on Sep 3, 2026
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
"No one was at the front desk to check in when we arrived, the check in process was impersonal once they showed up. No greeting, no acknowledgment that I had been waiting. The room was spacious, but beat up, holes in the wall, door/sink scratched, remote and phone dirty. Parking was easy, location ..."
Reviewed on Sep 2, 2026
Find cheap hotels in Chestertown
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Frequently Asked Questions About Chestertown hotels
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