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 $208 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](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) ![](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 [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Historic Hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1870) "Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/fda5370c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/w1857h2500x0y0-ac5cefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (79) "Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $182 CA $208 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/226d6f82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/8a68c06d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/1f4387ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008100/19008016/76c1b6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hidden Fells Point Gem / Private Courtyard Patio Fells Point 9.6/10 Exceptional (89) "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](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward J. CA $86 CA $290 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-Courtyard-Your-Historically-Restored-Apartment.h19008016.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/d1715c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/69872362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 19.90 per person)](https://images.trvl-media.com/lodging/1000000/890000/890000/889993/b358be96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel Fells Point 9.2/10 Wonderful (746) "Really lovely stay- clean and very helpful staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $188 CA $249 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/65ec141b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/0d7cc499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/44aeb3af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/20000000/19010000/19008000/19007969/2c031a65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Fells Point Gem / In The Heart of Fells Point Fells Point 9.8/10 Exceptional (198) "Great place all around " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophia F. CA $86 CA $290 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Baltimore-Hotels-At-Fells-Point-CitySide-Tons-Better-Than-A-Hotel.h19007969.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/a8bf1b01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/6d339134.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, City View](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/eaea568e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/116000000/115970000/115964600/115964505/8d2066be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 86 State Circle - Luxury Boutique Hotel Historic District 10/10 Exceptional (2) "Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels." ![Norway](https://a.travel-assets.com/egds/marks/flags/no.svg) Jo CA $481 CA $549 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-86-State-Circle-Luxury-Boutique-Hotel.h115964505.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/fc34c762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/5acb80c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/4de85be2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/43000000/42020000/42019100/42019059/081c863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy 2br home w/ parking in downtown Annapolis Historic District 10/10 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](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheldon E. CA $163 CA $429 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Annapolis-Hotels-Cozy-2br-Home-W-Parking-In-Downtown-Annapolis.h42019059.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/3fe6d96d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/2ec17b55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/62f27275.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23930000/23927100/23927080/366316a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs Canton 9.8/10 Exceptional (65) "Cute and quiet neighborhood with a beautiful view of the park. The host made it a stress free stay with great tips." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller CA $188 CA $379 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Baltimore-Hotels-Luxury-Parkfront-Haven-With-Hot-Tub-Beloved-By-Families-Their-Dogs.h23927080.Hotel-Information) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/af277faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/658d4a6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/a6c44038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Baltimore Fells Point 9.4/10 Exceptional (1000) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) kimberly CA $469 CA $608 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1014h600x10y12-4e8a8c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/598d88e9_edited_b6ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/001f8463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92570000/92564900/92564827/w1024h592x0y17-9d1e8161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 18th Cent. Charm in Historic Downtown Annapolis Historic District 9.0/10 Wonderful (13) "Property description is accurate, host is quickly responsive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradford R. CA $238 CA $482 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Annapolis-Hotels-Charming-18th-Cent-Home-In-Historic-Downtown-Annapolis.h92564827.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=2025-11-13&endDate=2025-11-14®ionId=7215&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Chestertown Hotel Reviews ![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 "Clean room and quiet enough to sleep through the afternoon. " [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.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 "Lovely room" [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.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 "We went on a family weekend getaway. The hotel is a few minutes drive from the harbor. The pool was a favorite with the kids . We loved the fact the comedy club and safari night club was conveniently located on the property. The breakfast needed other meat options other than pork sausage, a beef or turkey bacon would’ve been better options . The hotel was clean , security was phenomenal especially during event times keeping hotel guest secure. I would definitely stay here again " [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](//images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "Will definitely be back again 🙌" [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "Love it always " [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.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 "Clean room. Friendly staff awesome location. " [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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 "Well received by front desk attendant. Clean room! " [](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 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 Chesapeake Bay and Chestertown Dog Park exemplify the area's natural beauty. 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. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Baltimore](https://www.expedia.ca/Baltimore-Hotels-Hotels-With-A-Lazy-River.0-0-d178235-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Belcamp](https://www.expedia.ca/Belcamp-Hotels-Cheap-Hotels.0-0-d602125-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Belcamp](https://www.expedia.ca/Belcamp-Hotels-Family-Hotel.0-0-d602125-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Apartments in Betterton](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - 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