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Find Historic Hotels in Chestertown, MD

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Check availability on Chestertown Historic Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

Top Chestertown Historic Hotels

86 State Circle - Luxury Boutique Hotel
Exterior

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."
The price is NT$11,524
NT$13,138 total
includes taxes & fees
Oct 8 - Oct 9
86 State Circle - Luxury Boutique Hotel
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1837)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
134 Prince - Luxury Boutique Hotel
Exterior

134 Prince - Luxury Boutique Hotel

2.5 star property
9.8 out of 10, Exceptional, (26)
"Very friendly staff!"
134 Prince - Luxury Boutique Hotel
Flag House Inn
Front of property

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (79)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is NT$7,142
NT$8,142 total
includes taxes & fees
Nov 2 - Nov 3
Flag House Inn
The Inn at Henderson's Wharf, an Ascend Collection Hotel
View from room

The Inn at Henderson's Wharf, an Ascend Collection Hotel

3.0 star property
9.2 out of 10, Wonderful, (736)
"Great location and very friendly staff! "
The price is NT$4,880
NT$6,338 total
includes taxes & fees
Nov 2 - Nov 3
The Inn at Henderson's Wharf, an Ascend Collection 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Beautiful hotel in the heart of Annapolis. Lots of charm "
Sara 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

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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.