Title: Rolling Road Park in Chestertown - Tours and Activities | Expedia.ca [Rolling Road Park Hotels](https://expedia.ca/Rolling-Road-Park-Hotels.0-l924439484834201600-0.Travel-Guide-Filter-Hotels)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Rolling Road Park Car Rentals](https://expedia.ca/Car-Rentals-In-Rolling-Road-Park.d924439484834201600.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) # Rolling Road Park Tours and Activities ## Visit Rolling Road Park Activities [Chestertown travel guide](https://expedia.ca/Chestertown.dx7215) --- --- ## Plan a trip to see Rolling Road Park Price found within the past 48 hours. Click for updated prices. ![Boardwalk One](https://images.trvl-media.com/lodging/3000000/2060000/2053600/2053558/73b85086_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Boardwalk One Downtown Ocean City CA $1,123 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 7.4/10 Good! (170 reviews) Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo. Reviewed on Oct 1, 2025 ![Grand Hotel Ocean City Oceanfront](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/35e46ff3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grand Hotel Ocean City Oceanfront Downtown Ocean City CA $1,234 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 9/10 Wonderful! (3,316 reviews) Clean room , great view , efficient check in Reviewed on Dec 11, 2025 ![Motel 6 Salisbury, MD](https://images.trvl-media.com/lodging/1000000/860000/855500/855472/f5802738_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Motel 6 Salisbury, MD CA $2,111 per person Jan 26 - Feb 2 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Salisbury (SBY) 7.2/10 Good! (931 reviews) Room had 3 baby roaches in the bathroom that were quickly dispatched. However, the staff (Ms. Aimee) was very accommodating Reviewed on Nov 30, 2025 ### Popular places to visit #### Chestertown Dog Park Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene. [](https://expedia.ca/Chestertown-Dog-Park-Chestertown.d906189322804744192.Vacation-Attraction) #### 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) #### 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) #### 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) #### 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) #### Chestertown Historic District Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene. [](https://expedia.ca/Chestertown-Historic-District-Chestertown.d950929327394992128.Vacation-Attraction) --- ## Best Lodging Options Near Rolling Road Park ## Check availability on hotels close to Rolling Road Park [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=2025-12-13&endDate=2025-12-14)[Dec 13 - Dec 14](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=2025-12-13&endDate=2025-12-14) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=2025-12-14&endDate=2025-12-15)[Dec 14 - Dec 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=2025-12-14&endDate=2025-12-15) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=924439484834201600&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) ![Hilton Garden Inn Kent Island Marina](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_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) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_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) ![SpringHill Suites Baltimore White Marsh/Middle River](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_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) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Americas Best Value Inn Edgewood 1709 Edgewood Road Edgewood MD [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Quality Inn & Suites Bel Air I-95 Exit 77A 2112a Emmorton Park Road Edgewood MD [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_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) ![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) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_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) ![La Quinta Inn & Suites by Wyndham Aberdeen-APG](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG 793 W Bel Air Ave Aberdeen MD [](https://expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) [See all 2,027 properties in Rolling Road Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=924439484834201600) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. 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