Find Historic Hotels in Chestertown, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Historic Hotels

Our top choices for Chestertown historic hotels

Meeting facility
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
Historic Inns of Annapolis
Bar (on property)
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
The price is AED 1,310
AED 1,493 total
includes taxes & fees
16 Dec - 17 Dec
86 State Circle - Luxury Boutique Hotel
Exterior
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
The price is AED 559
AED 730 total
includes taxes & fees
2 Jan - 3 January 2026
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Lobby lounge
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
The price is AED 700
AED 799 total
includes taxes & fees
16 Dec - 17 Dec
Flag House Inn
Interior
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.
The price is AED 202
AED 725 total
includes taxes & fees
14 Dec - 15 Dec
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.
The price is AED 202
AED 725 total
includes taxes & fees
14 Dec - 15 Dec
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
134 Prince - Luxury Boutique Hotel
Exterior
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.
The price is AED 488
AED 1,056 total
includes taxes & fees
18 Dec - 19 Dec
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.
The price is AED 496
AED 2,583 total
includes taxes & fees
15 Dec - 16 Dec
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.
The price is AED 698
AED 1,474 total
includes taxes & fees
5 Jan - 6 January 2026
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.
View all properties

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

Explore a world of travel with Expedia

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.