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) --- --- ## Plan a trip to see Chestertown Historic District Price found within the past 48 hours. Click for updated prices. ![Sahara Motel](https://images.trvl-media.com/lodging/91000000/90730000/90727700/90727609/df290b50_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sahara Motel Downtown Ocean City CA $755 per person May 4 - May 8 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Salisbury (SBY) 7.8/10 Good! (520 reviews) I was very happy with our room - loved being on the first floor. I plan to return next time I come to the beach. Reviewed on Oct 31, 2025 ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/7811430e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City CA $892 per person May 4 - May 8 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Salisbury (SBY) 9/10 Wonderful! (3,461 reviews) Clean room and facility. Parking lot was for larger SUVS but that was not enforced and we had to park on street as our vehicle would not fit in parking garage. When checking in it seemed to be a bother and no apologies for lack of parking in February, hate to think what it would be like in summer. I merely asked where we could park. Never got an enjoy your stay or explanation of facilities. The checkout was polar opposite pleasant and asked about our stay and hoped we would return Reviewed on Mar 12, 2026 ![Plim Plaza Hotel](https://images.trvl-media.com/lodging/2000000/1570000/1565700/1565623/002c5ef6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Plim Plaza Hotel Downtown Ocean City CA $874 per person May 4 - May 8 found 15 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Salisbury (SBY) 7.4/10 Good! (1,002 reviews) Great location, staff did a wonderful job for a busy off season weekend. Reviewed on Dec 4, 2025 ### 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=2026-03-20&endDate=2026-03-21)[Mar 20 - Mar 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-20&endDate=2026-03-21) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-21&endDate=2026-03-22)[Mar 21 - Mar 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=950929327394992128&startDate=2026-03-21&endDate=2026-03-22) [This 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/w5755h3835x5y5-a7434888_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) ![SpringHill Suites Baltimore White Marsh/Middle River](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/d7725583_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SpringHill Suites Baltimore White Marsh/Middle River 6110 Greenleigh Avenue Middle River MD [](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.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) ![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 2,119 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.