Title: Book the Best HISTORIC Hotels in Chestertown in 2025 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Historic Hotels in Chestertown, MD from CA $125 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chestertown Historic Hotels Tonight [Sep 25 - Sep 26](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-09-25&endDate=2025-09-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 26 - Sep 27](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-09-26&endDate=2025-09-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Historic Hotels ## Our top choices for Chestertown historic hotels ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/39c19e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/1680c746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/4b182ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/37d3c420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Chestertown 9.8/10 Exceptional (84) "We had a wonderful weekend. Thank you!" [](https://www.expedia.ca/Chestertown-Hotels-Chester-River-Waterfront.h18994126.Hotel-Information) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown 7.2/10 Good (396) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." CA $113 CA $125 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-09&endDate=2025-10-10®ionId=7215&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![The Inn at Henderson's Wharf, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel 10/10 Excellent " Very nice" [](https://expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "The staff were professional and friendly. " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](//images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Clean and quiet " [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Stayed for one night; room was nice, easy to access, and located near numerous local attractions. " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](//images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Y" [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Really nice!" [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](//images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "good" [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](//images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "another top notch stay at Hampton Inn. Only hotels, I will stay at. Always clean, friendly, and accommodating" [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Red Roof Inn & Suites Chestertown](//images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737_y.jpg) ### Red Roof Inn & Suites Chestertown 10/10 Excellent "Time to upgrade the furniture in the rooms. The staff is doing a GREAT JOB cleaning and providing excellent service. " [](https://expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ## 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. University life is a highlight and campuses to tour include Washington College and River Arts Chestertown. 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. 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