Title: Chestertown Historic District in Chestertown - Tours and Activities | Expedia.ca [Chestertown Historic District Hotels](https://expedia.ca/Chestertown-Historic-District-Hotels.0-l950929327394992128-0.Travel-Guide-Filter-Hotels)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Historic District Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown-Historic-District.d950929327394992128.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) # Chestertown Historic District Tours and Activities ## Visit Chestertown Historic District Activities [Chestertown travel guide](https://expedia.ca/Chestertown.dx7215) --- --- ### Popular places to visit ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Washington College Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Washington-College-Chestertown.d553248621561000403.Vacation-Attraction) #### Garfield Center for the Arts at the Prince Theater You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction) #### Historical Society of Kent County Maryland You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) #### Sumner Hall You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene. [](https://expedia.ca/Sumner-Hall-Chestertown.d948699115888525312.Vacation-Attraction) #### River Arts Chestertown Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area. [](https://expedia.ca/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) #### Wilmer Park Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals. [](https://expedia.ca/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) --- ## Best Lodging Options Near Chestertown Historic District ## Check availability on hotels close to Chestertown Historic District [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-11&endDate=2026-03-12)[Mar 11 - Mar 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-11&endDate=2026-03-12) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-12&endDate=2026-03-13)[Mar 12 - Mar 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-12&endDate=2026-03-13) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026)[Mar 13 - Mar 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=13%2F03%2F2026&endDate=15%2F03%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026)[Mar 20 - Mar 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=20%2F03%2F2026&endDate=22%2F03%2F2026) ![Best Western Kent Narrows Inn](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Kent Narrows Inn 3101 Main Street Grasonville MD [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Place Kent Narrows & Marina 3028 KENT NARROW WAY S Grasonville MD [](https://expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/2360f1f3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Kent Island Marina 3206 Main St Grasonville MD [](https://expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![The Inn at Chesapeake Bay Beach Club](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Inn at Chesapeake Bay Beach Club 180 Pier One Road Stevensville MD [](https://expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area](https://images.trvl-media.com/lodging/1000000/60000/56500/56432/w1822h1320x8y2-6d9bb9d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area 1807 Edgewood Rd Edgewood MD [](https://expedia.ca/Edgewood-Hotels-Wingate-By-Wyndham-Bel-Air-I-95-Exit-77A.h56432.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/38012dd1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Edgewood/Aberdeen-South 2110 Emmorton Park Rd Edgewood MD [](https://expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/c6a165a6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 2112b Emmorton Park Rd Edgewood MD [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Homewood Suites by Hilton Bel Air](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f058e662_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Homewood Suites by Hilton Bel Air 4170 Philadelphia Road Bel Air MD [](https://expedia.ca/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) ![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Aberdeen near APG 980 Hospitality Way Aberdeen MD [](https://expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) [See all 2,132 properties in Chestertown Historic District](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=950929327394992128) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX_POI_Spring_PROMO_950929327394992128)