Find Historic Hotels in Chestertown, MD

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Our top choices for Chestertown historic hotels

Terrace/patio
Historic Inns of Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1898)
"Great staff, comfortable beds, clean rooms and perfect location "
United States
Dawn
$164 nightly
The price is $187
Dec 21 - Dec 22
Total with taxes and fees
Historic Inns of Annapolis
Exterior
86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
$349 nightly
The price is $398
Dec 16 - Dec 17
Total with taxes and fees
86 State Circle - Luxury Boutique Hotel
View from room
The Inn at Henderson's Wharf, an Ascend Collection Hotel

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

The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0 star property
Fells Point
9.2 out of 10, Wonderful, (751)
"Really lovely stay- clean and very helpful staff! "
United States
Sean
$169 nightly
The price is $199
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Front of property
Flag House Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.4 out of 10, Exceptional, (83)
"The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. "
United States
Elizabeth
$191 nightly
The price is $217
Dec 16 - Dec 17
Total with taxes and fees
Flag House Inn
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (92)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
$171 nightly
The price is $198
Dec 14 - Dec 15
Total with taxes and fees
Hidden Fells Point Gem / Private Courtyard Patio
Marina
Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (200)
"Great place all around "
United States
Sophia F.
$171 nightly
The price is $198
Dec 14 - Dec 15
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
Exterior
134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (30)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
$213 nightly
The price is $243
Dec 14 - Dec 15
Total with taxes and fees
134 Prince - Luxury Boutique Hotel
Fridge, microwave, oven, stovetop
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Canton
9.8 out of 10, Exceptional, (65)
"Brandon was a thoughtful host and responded quickly. The property was lovely and so convenient. "
United States
andrea s.
$249 nightly
The price is $287
Dec 18 - Dec 19
Total with taxes and fees
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
Interior
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!

Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$617 nightly
The price is $703
Dec 15 - Dec 16
Total with taxes and fees
Historic Row Home with Hot Tub- 1 Block from Gate 1 at USNA!
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$352 nightly
The price is $401
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 2br home w/ parking in downtown 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.
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Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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 38 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. The picturesque setting of Northern Chesapeake Bay and Chesapeake Bay exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Chestertown Historic District and Rolphs Wharf Marina.
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.

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