An aerial view of a town with a river, buildings, and surrounding greenery.

Find Historic Hotels in Chestertown, MD from CA $200

  • 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

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chestertown historic hotels

A historic brick building with a corner turret and multiple windows, located on a city street with flags and street lamps.

1. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,059 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is CA $133
CA $200 total
includes taxes & fees
Nov 29 - Nov 30
Historic Inns of Annapolis
A wooden deck with wicker furniture, a round table, and a fire pit.

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is CA $503
CA $929 total
includes taxes & fees
Nov 2 - Nov 3
Chesapeake Cottages- 2 Quaint Waterfront Retreats
A kitchen with wooden cabinets, a microwave, a coffee maker, and a dishwasher.

3. 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, (217 reviews)
"It’s a cozy, clean, and cute apartment. We enjoyed our stay very much and the location is wonderful…within walking distance of all the restaurants and attractions you could want."
United States
Carol
The price is CA $82
CA $320 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Fells Point Gem / In The Heart of Fells Point
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

4. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (102 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $82
CA $321 total
includes taxes & fees
Nov 8 - Nov 9
Hidden Fells Point Gem / Private Courtyard Patio
A house with a red door, a small porch, and a view of a river with a bridge in the background.

5. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $496
CA $725 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Three birds perched on a wooden structure by the water.

6. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,117
CA $1,934 total
includes taxes & fees
Nov 2 - Nov 3
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
A two-story house with a backyard swimming pool, surrounded by trees and a well-maintained lawn.

7. 4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!

4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (44 reviews)
"Fantastic, property, location and positive interaction with owner."
United States
David R.
The price is CA $1,117
CA $1,934 total
includes taxes & fees
Nov 2 - Nov 3
4 Bedroom Waterview - MD Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
A waterfront walkway with a brick path, a lamp post, and a bench.

8. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is CA $405
CA $744 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 2br home w/ parking in downtown Annapolis
Exterior detail

9. 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, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is CA $301
CA $752 total
includes taxes & fees
Nov 2 - Nov 3
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Parking was tough until it was made clear we can park in neighboring lots. Breakfast was pleasant staff warm and helpful. We love La Quinta and will be back!"
sheila 3-night trip
Posted 7 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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 45 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.

Explore a world of travel with Expedia