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Find Historic Hotels in Chestertown, MD

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Check availability on Chestertown Historic Hotels

Compare Chestertown Historic Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (335)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
The price is AED 205
AED 227 total
includes taxes & fees
18 Mar - 19 Mar
Red Roof Inn & Suites Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What can I expect on my historical trip to Chestertown?
You’ll probably want to seek out the places with historical relevance during your vacation in Chestertown. You can also enjoy the many sights including the sporting events and university setting
How many historical hotels will I find in Chestertown?
Chestertown is home to 41 hotels and other accommodations bookable on Expedia though not many historic hotels to choose from.
What are the must-see historical places and other sights to visit in Chestertown?
Chestertown is notable for landmarks like Historical Society of Kent County Maryland. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. A couple of additional sights to add to your agenda are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
What is a historic hotel like in Chestertown?
When you choose a historic hotel, you’ll stay someplace that has an officially recognized historic designation. A palace, castle, stately home or even a lodge, pub, or skyscraper can be identified as a historic hotel as long as it has special significance. Traditional architecture and period features can be admired within the guestrooms or public spaces of these historic hotels in Chestertown, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
“Heritage hotel” is more common in Asia and Europe, while “historic hotel” is more common in the U.S. but overall the terms are quite similar. The architecture and actual building of historic hotels tend to be what’s most important. For a heritage hotel, it’s mainly the cultural value and how it influenced the community.
Do historic hotels in Chestertown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, but every effort is made to preserve treasured traditions and historic facades. Smart TVs, WiFi, updated bathroom facilities, and the usual amenities found at a contemporary hotel will be available in a historic hotel. Rest assured that when you select a historic hotel in Chestertown, you won’t find yourself staying at a place that’s uncomfortable or rundown.