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With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
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Most Popular Hotels
as Ranked by TripAdvisor™ Travelers
2-Star Hotel
Holiday Inn Express Hotel & Suites Chestertown
Holiday Inn Express Hotel & Suites Chestertown
Traveler Rating:4.5 of 5 stars
Latest review: "This place is SOLID"
This hotel has all the essentials of a great hotel. Its clean, quiet, everything works, the bed and pillows are very comfortable, the staff friendly and...
Check Rates    Average price*: $138
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Brampton Bed & Breakfast Inn
Brampton Bed & Breakfast Inn
Traveler Rating:5.0 of 5 stars
Latest review: "Splendid!!!"
My husband and I stayed at the Brampton Inn for a night over the 4th of July weekend....and our only disappointments were 1) that our trip was too short...
Check Rates    Average price*: $199
Great Oak Manor Inn
Traveler Rating:5.0 of 5 stars
Latest review: "Great Oak Manor, so nice we had to try it twice!"
It hasn't even been an entire year since we last visited the Great Oak Manor in Chestertown, MD when we received an email from Cassandra, the Innkeeper...
Average price*: $237
Comfort Suites
Comfort Suites
Traveler Rating:4.5 of 5 stars
Latest review: "Comfortable and friendly"
Everyone was friendly at the front desk. The rooms was spacious and clean. The breakfast room was clean.
Check Rates    Average price*: $133
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Looking for things to do in Chestertown? Check out our page of things to do in Chestertown!
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