Title: Chestertown, MD Car Rental - Free Cancellation Options - Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Vacation Packages](https://expedia.com/Chestertown.d7215.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Car Rental Chestertown, MD ## Search and Compare from Car Companies in Chestertown ## Featured car rental suppliers Compare from agencies ![car suppliers logo](https://forever.travel-assets.com/flex/flexmanager/images/2022/02/16/car-suppliers-logo-desktop.jpg) - ![protection illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__protection.svg) ### Change your mind Penalty-free cancellation on many/select car rentals - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself One Key members save 10% or more on over 1 million car rentals [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![package illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__package.svg) ### Shop smart Compare car suppliers and package your flight, hotel, and car to save ## Top Car Deals in Chestertown \* Price found within the past 6 days. Click for updated prices. ### Economy Chevrolet Spark or similar - 4 people Chestertown, Maryland, USA ![Chevrolet Spark](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_EC.png) [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=4/2/2026&date2=4/4/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22economy%22]) ### Compact Ford Focus or similar - 4 people Chestertown, Maryland, USA ![Ford Focus](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_CC.png) [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=4/2/2026&date2=4/4/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22compact%22]) ### Midsize Toyota Corolla or similar - 5 people Chestertown, Maryland, USA ![Toyota Corolla](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_IC.png) [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=4/2/2026&date2=4/4/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22midsize%22]) ### SUV Jeep Compass or similar - 5 people Chestertown, Maryland, USA ![Jeep Compass](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_SF.png) [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=4/2/2026&date2=4/4/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car rentals in Chestertown [View all cars](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=4/2/2026&date2=4/4/2026&crfrr=defaultFlex&SearchType=Place) ## Frequently asked questions ### How much is a rental car per day in Chestertown? ### What happens if I need to cancel my Chestertown car reservation? ### Where can I go on a road trip from Chestertown? > - Washington is around 55 miles from Chestertown. Famous tourist attractions like White House should be at the top of your list here. > - Why not see everything on offer in Alexandria too? Major sights here include George Washington Masonic National Memorial. Alexandria is 60 miles from Chestertown. > - Battery Park is located 150 miles from Chestertown and is one of the region's most gorgeous nature spots. Go for a wander around and enjoy the fresh air here. ### How do I find the best car rental deals in Chestertown with Expedia? ### How old do you have to be to rent a car in Chestertown? ### What do you need to rent a car in Chestertown? ### What is the cheapest car rental in Chestertown? ### Can I rent a car for a month or longer in Chestertown? ### Where can I find a Chestertown car rental if I am younger than 25? ### What insurance should I choose for my car rental in Chestertown? ## Car Rental Information | Popular car types | [SUV](https://www.expedia.com/lp/b/car-rental/suv?rfrr=car.table.SUV), [Full Size](https://www.expedia.com/lp/b/car-rental/fullsize?rfrr=car.table.FullSize), [Economy](https://www.expedia.com/lp/b/car-rental/economy?rfrr=car.table.Economy) | | ------------------------------------------------ | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Car suppliers available | | | Our best deal of the day | | | Our second best deal of the day | | | Our third best deal of the day | | | From the airport to your hotel | [Airport Transportation](https://www.expedia.com/ground-transfers?rfrr=car.table.AirportTransportation) | | From popular domestic and international airports | [Airport Car Rentals](https://www.expedia.com/lp/b/car-rental/airport) | ### **Finding the cheapest car rentals in Chestertown** ### **Using our Search Wizard** If the deals that are available on our page do not suit your needs, then enter Chestertown into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Chestertown and provide you with a list of the cheapest options, with no added fees. ### **Renting a car in Chestertown** Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Chestertown. We partner with reliable partners that guarantee an enjoyable experience for solo travelers, couples, and families. Package your car with a flight or hotel to unlock even more savings from Expedia. ### **Expected prices in Chestertown** Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book . ### **Flexibility & Cancellation** Most car suppliers offer penalty-free cancellations, so you don’t have to worry about losing money if your plans change. To cancel your booking log into your account through the [Trips](https://www.expedia.com/trips) portal. Click manage booking and cancel this car. If you needed to alter your booking, then you can create a new one once you have canceled. ### **We all love being rewarded** [One Key](https://www.expedia.com/welcome-one-key?langid=1033) members save 10% or more on select hotels, cars, activities and vacation rentals. Not only that, earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands: Expedia, Hotels.com and VRBO. Learn more and join today. ### **Car classes available from Expedia in 2026** The classes of vehicles available will change depending on your chosen location. - [Compact car rentals](https://www.expedia.com/lp/b/car-rental/compact) - [Convertible car rentals](https://www.expedia.com/lp/b/car-rental/convertible) - [Economy car rentals](https://www.expedia.com/lp/b/car-rental/economy) - [Fullsize car rentals](https://www.expedia.com/lp/b/car-rental/fullsize) - [Luxury car rentals](https://www.expedia.com/lp/b/car-rental/luxury) - [Midsize car rentals](https://www.expedia.com/lp/b/car-rental/midsize) - [Mini car rentals](https://www.expedia.com/lp/b/car-rental/mini) - [Minivan rentals](https://www.expedia.com/lp/b/car-rental/minivan) - [Pickup car rentals](https://www.expedia.com/lp/b/car-rental/pickup) - [Premium car rentals](https://www.expedia.com/lp/b/car-rental/premium) - [Sportscar rentals](https://www.expedia.com/lp/b/car-rental/sportscar) - [Standard car rentals](https://www.expedia.com/lp/b/car-rental/standard) - [SUV rentals](https://www.expedia.com/lp/b/car-rental/suv) - [Van rentals](https://www.expedia.com/lp/b/car-rental/van) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - [Hotels near Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) - [Hotels near Wilmer Park ](https://www.expedia.com/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels) - 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[River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Chestertown.d553248621532662298.Vacation-Attraction) - [Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Chestertown.d553248621561000400.Vacation-Attraction) - [Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Chestertown.d553248621561000401.Vacation-Attraction) - [Wilmer Park ](https://www.expedia.com/Wilmer-Park-Chestertown.d553248621561000402.Vacation-Attraction) - [Rolphs Wharf Marina ](https://www.expedia.com/Rolphs-Wharf-Marina-Chestertown.d553248621561879605.Vacation-Attraction) - [Worton Vacations ](https://www.expedia.com/Worton.d3000440948.Destination-Travel-Guides) - [Visit Worton ](https://www.expedia.com/Worton.dx3000440948) - [Visit Church Hill ](https://www.expedia.com/Church-Hill.dx6359186) - [Cassinelli Winery and Vineyards ](https://www.expedia.com/Cassinelli-Winery-And-Vineyards-Church-Hill.d553248621561879606.Vacation-Attraction) - [Visit Kennedyville ](https://www.expedia.com/Kennedyville.dx3000440679) - [Visit Still Pond ](https://www.expedia.com/Still-Pond.dx3000347996) - [Visit Great Oak Landing ](https://www.expedia.com/Great-Oak-Landing.dx3000045661) - [Visit Crumpton ](https://www.expedia.com/Crumpton.dx3000440547) - [Visit Betterton ](https://www.expedia.com/Betterton.dx3000440429) - [Visit Rock Hall ](https://www.expedia.com/Rock-Hall.dx177447) - [Rock Hall Vacations ](https://www.expedia.com/Rock-Hall.d177447.Destination-Travel-Guides) - [The Mainstay ](https://www.expedia.com/The-Mainstay-Rock-Hall.d553248621532662296.Vacation-Attraction) - [Rock Hall Harbor ](https://www.expedia.com/Rock-Hall-Harbor-Rock-Hall.d553248621561173703.Vacation-Attraction) - [Waterman’s Museum ](https://www.expedia.com/Watermans-Museum-Rock-Hall.d673471647360921600.Vacation-Attraction) - [Car rentals near Worton ](https://www.expedia.com/Car-Rentals-In-Worton.d3000440948.Car-Rental-Guide) - [Car rentals near Pomona ](https://www.expedia.com/Car-Rentals-In-Pomona.d553248635976007038.Car-Rental-Guide) - [Car rentals near Fairlee ](https://www.expedia.com/Car-Rentals-In-Fairlee.d553248635976006792.Car-Rental-Guide) - [Car rentals near Georgetown ](https://www.expedia.com/Car-Rentals-In-Georgetown.d553248635975874069.Car-Rental-Guide) - [Car rentals near Church Hill ](https://www.expedia.com/Car-Rentals-In-Church-Hill.d6359186.Car-Rental-Guide) - [Car rentals near Great Oak Landing ](https://www.expedia.com/Car-Rentals-In-Great-Oak-Landing.d3000045661.Car-Rental-Guide) - [Car rentals near Crumpton ](https://www.expedia.com/Car-Rentals-In-Crumpton.d3000440547.Car-Rental-Guide) - [Car rentals near Crumpton Auction ](https://www.expedia.com/Car-Rentals-In-Crumpton-Auction.d553248621532662415.Car-Rental-Guide) - [Car rentals near Edesville ](https://www.expedia.com/Car-Rentals-In-Edesville.d553248635976006323.Car-Rental-Guide) - [Car rentals near Tolchester Beach ](https://www.expedia.com/Car-Rentals-In-Tolchester-Beach.d553248635975848245.Car-Rental-Guide) - [Car rentals near Price ](https://www.expedia.com/Car-Rentals-In-Price.d553248635975875972.Car-Rental-Guide) - [Car rentals near Betterton ](https://www.expedia.com/Car-Rentals-In-Betterton.d3000440429.Car-Rental-Guide) - [Car rentals near Rock Hall ](https://www.expedia.com/Car-Rentals-In-Rock-Hall.d177447.Car-Rental-Guide) - [Avis Rental Cars in Rock Hall ](https://www.expedia.com/Avis-Car-Rentals-In-Rock-Hall.d177447-c41.Car-Rental-Guide-Suppliers) - [Great Oak Landing Vacation Rentals ](https://www.expedia.com/Great-Oak-Landing-Vacation-Rentals.d3000045661.Travel-Guide-VacationRentals) - [Betterton Vacation Rentals ](https://www.expedia.com/Betterton-Vacation-Rentals.d3000440429.Travel-Guide-VacationRentals) - [Rock Hall Vacation Rentals ](https://www.expedia.com/Rock-Hall-Vacation-Rentals.d177447.Travel-Guide-VacationRentals) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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