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Check availability on Chestertown Historic Hotels

Tonight
2 Aug - 3 Aug
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3 Aug - 4 Aug
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8 Aug - 10 Aug
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15 Aug - 17 Aug

Top Chestertown Historic Hotels

Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1814)
"Loved the hotel-great location "
Historic Inns of Annapolis
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.

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Friendly and accommodating they really didn’t try to help out"
David Brian 1-night trip
Posted 11 days ago
Hampton Inn Baltimore/Glen Burnie

Frequently asked questions

What should a history buff expect from a stay in Chestertown?
You'll probably want to seek out the places with historical relevance while you're staying in Chestertown. You can also explore the many sights including the sporting events and university setting.
What's the best accommodation in Chestertown to learn about local history?
Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi.
How many historical hotels will I find in Chestertown?
In Chestertown, you'll find 44 lodging options bookable on Expedia though you won't find many designated historic hotels.
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 itinerary are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
What is a historic hotel like in Chestertown?
Guests who choose a historic hotel can enjoy a holiday in a building that has a national historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of such hotels in Chestertown, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and building of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value along with how it shaped the community.
Do historic hotels in Chestertown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, though efforts have been made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in a hotel will be available in a historic hotel. When you choose a historic hotel in Chestertown, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.