Find Historic Hotels in Chestertown, MD

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Check availability on Chestertown Historic Hotels

Tonight
27 Apr - 28 Apr
Tomorrow
28 Apr - 29 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

Our top choices for Chestertown historic hotels

Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (95 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AED 217
AED 738 total
includes taxes & fees
29 Apr - 30 Apr
Hidden Fells Point Gem / Private Courtyard Patio
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 544
AED 1,269 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is AED 1,322
AED 2,441 total
includes taxes & fees
30 Apr - 1 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,843 reviews)
"Historic charm, lovely location, friendly, helpful staff."
United States
Anne
The price is AED 526
AED 725 total
includes taxes & fees
25 May - 26 May
Historic Inns of Annapolis
Exterior detail

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AED 1,137
AED 2,440 total
includes taxes & fees
28 Apr - 29 Apr
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Very good hotel but too expensive. Parking price was 50$, a rip off. We should have parked with an app. We didn’t expect the surprise in Annapolis. We pay that money in DC or NYC."
Sylvia 1-night trip
Posted 5 hours 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 42 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. Natural beauty is on display at Northern Chesapeake Bay, Chesapeake Bay, and Chestertown Dog Park. 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.