Photo by Patricia Knorr

Chestertown Historic Hotel

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Top Chestertown Historic Hotel

Newly restored apartment in the heart of Chestertown

Chestertown
9.8 out of 10, Exceptional, (27)
"Extremely clean, beautifully updated, and very comfortable. Perfect location—easy to walk to shops and restaurants. Would absolutely stay again!""
United States
Maggie D.
The price is HK$2,566
HK$3,727 total
includes taxes & fees
14 Nov - 15 Nov
Newly restored apartment in the heart of Chestertown

Flag House Inn

3.5 star property
Historic District
9.4 out of 10, Exceptional, (80)
"Overpriced for what it offered. $500+ for a single night at the property sans breakfast or parking. Room itself was small with no real historic flair or charm. Found a used washcloth on the floor housekeeping had overlooked. To check in during peak hours we had to call hotel staff (attending to other properties when we arrived) in order to get access to the room. If this property were about $200 less expensive, I would have zero complaints, but to spend that amount of money I expected way...
United States
Kathy
The price is HK$813
HK$926 total
includes taxes & fees
9 Nov - 10 Nov
Flag House Inn

Historic Inns of Annapolis

3.5 star property
Historic District
9.0 out of 10, Wonderful, (1875)
"Great location "
United States
Karyl
Historic Inns of Annapolis

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

3.0 star property
Fells Point
9.2 out of 10, Wonderful, (748)
"The bed was extremely comfortable and the room was cozy, and the front desk staff were helpful and friendly!"
United States
Natalie
The price is HK$1,113
HK$1,462 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Henderson's Wharf, an Ascend Collection Hotel

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point
9.6 out of 10, Exceptional, (89)
"Lenny’s apartment was the perfect base for our Baltimore visit! It’s just a short walk to the water where there are shops, restaurants and bars. The space is cozy, has everything you need to make meals and was very clean. Lenny was quick to respond to questions and was very accommodating. Thanks for a great stay! "
United States
Maureen S.
The price is HK$459
HK$1,563 total
includes taxes & fees
9 Nov - 10 Nov
Hidden Fells Point Gem / Private Courtyard Patio

134 Prince - Luxury Boutique Hotel

2.5 star property
Annapolis
9.8 out of 10, Exceptional, (28)
"Very friendly staff!"
United States
Richard
134 Prince - Luxury Boutique Hotel

Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point
9.8 out of 10, Exceptional, (198)
"Awesome alternative to a hotel, perfect location, walking distance to all Fells Point attractions, bars and restaurants."
United States
Sue
The price is HK$482
HK$1,617 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Fells Point Gem / In The Heart of Fells Point

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

Canton
9.8 out of 10, Exceptional, (65)
"This was the best VRBO experience we've ever had. The property was exactly as described, the location was fantastic, and the rental property was the best stocked property we've ever experienced. Absolutely perfect?"
United States
Bill H.
The price is HK$1,104
HK$2,174 total
includes taxes & fees
18 Nov - 19 Nov
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

86 State Circle - Luxury Boutique Hotel

2.0 star property
Historic District
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."
Norway
Jo
The price is HK$2,507
HK$2,857 total
includes taxes & fees
9 Nov - 10 Nov
86 State Circle - Luxury Boutique Hotel

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (71)
"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 HK$918
HK$2,393 total
includes taxes & fees
17 Nov - 18 Nov
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.

Top Chestertown Hotel Reviews

Frequently asked questions

What should a history buff expect from a stay in Chestertown?
You'll probably want to seek out the places with historical relevance while you're staying in Chestertown. You can also explore the many sights including the sporting events and university setting.
How many historical hotels will I find in Chestertown?
In Chestertown, you'll find 39 lodging options bookable on Expedia though you won't find many designated historic hotels.
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 Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
What is a historic hotel like in Chestertown?
Guests who choose a historic hotel can enjoy a holiday in a building that has a national historic designation. A castle, a palace or even a pub or an old police station can be transformed into a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the communal spaces and guestrooms of such hotels in Chestertown, giving a historical feel.
What is the difference between a historic hotel and a heritage hotel?
You'll often hear the term "heritage hotel" in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and building of a historic hotel tends to be what's most significant. For a heritage hotel, it's often the cultural value along with how it shaped the community.
Do historic hotels in Chestertown have modern facilities?
Hotel interiors feature the modern conveniences and safety features you expect to find, though efforts have been made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the usual amenities found in a hotel will be available in a historic hotel. When you choose a historic hotel in Chestertown, don't worry that you'll find yourself staying at a place that's uncomfortable for guests or simply rundown.