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Search Historic Hotels in Chestertown

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Check availability on Chestertown Historic Hotels

Tonight
1 Nov - 2 Nov
Tomorrow
2 Nov - 3 Nov
Next weekend
7 Nov - 9 Nov
In two weeks
14 Nov - 16 Nov

Top Chestertown Historic Hotels

Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1871)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
Front of property
Flag House Inn
Flag House Inn
3.5 star property
9.4 out of 10, Exceptional, (79)
"Great place to stay when visiting Annapolis."
United States
Kevin
The price is ฿4,226
฿4,817 total
includes taxes & fees
2 Nov - 3 Nov
Flag House Inn
View from room
The Inn at Henderson's Wharf, an Ascend Collection Hotel
The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
9.2 out of 10, Wonderful, (746)
"Beautiful location and a great stay. Eric at the front desk was great!"
United States
dena
The price is ฿4,369
฿5,777 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
9.8 out of 10, Exceptional, (28)
"Very friendly staff!"
United States
Richard
134 Prince - Luxury Boutique Hotel
Exterior
86 State Circle - Luxury Boutique Hotel
86 State Circle - Luxury Boutique Hotel
2.0 star property
10.0 out of 10, Exceptional, (2)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is ฿11,330
฿12,916 total
includes taxes & fees
2 Nov - 3 Nov
86 State Circle - Luxury Boutique Hotel
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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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again "
Jannelle 2-night trip
Posted 6 days ago
Best Western Plus Hotel & Conference Center

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.
How many historical hotels will I find in Chestertown?
In Chestertown, you'll find 37 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. The picturesque setting of Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. 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.