Title: Chestertown Car Rental, MD - Search & Compare - Expedia.ca​ [Chestertown Travel Guide](https://expedia.ca/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Vacation Packages](https://expedia.ca/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) # Chestertown Car Rental ## Search and Compare from Car Companies in Chestertown ## Featured car rental suppliers Compare from agencies ![car supplier logos](https://forever.travel-assets.com/flex/flexmanager/images/2022/05/16/BEXCA-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 Members save 10% or more on over 1 million car rentals - ![package illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__package.svg) ### Shop smart Compare car suppliers to unlock big savings ## Top Car Deals in Chestertown \* Price found within the past 6 days. Click for updated prices. Mon, Mar 2 - Tue, Mar 3 ### Compact Nissan Versa or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Nissan Versa](//mediaim.expedia.com/cars/15/d2536e4a-ab88-4f61-a592-64c1f5793e62.jpg) #### CA $103 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=89.01&tprfrr=102.66&cvrfrr=ET&ctrfrr=CC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22compact%22]) Mon, Mar 2 - Tue, Mar 3 ### Economy Mitsubishi Mirage or similar - 4 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Mitsubishi Mirage](//mediaim.expedia.com/cars/15/e33a3a8e-ab43-4517-9031-521bd1e766df.jpg) #### CA $103 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=89.01&tprfrr=102.66&cvrfrr=ET&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Mon, Mar 2 - Tue, Mar 3 ### Midsize Toyota Corolla or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Toyota Corolla](//mediaim.expedia.com/cars/15/f000f182-e906-41c9-acfe-807d645a2fcc.jpg) #### CA $106 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=91.75&tprfrr=105.72&cvrfrr=ET&ctrfrr=IC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Mon, Mar 2 - Tue, Mar 3 ### Standard Volkswagen Jetta or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Volkswagen Jetta](//mediaim.expedia.com/cars/15/f5ef6d5a-8651-4374-8368-b1605fd59b02.jpg) #### CA $109 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=94.49&tprfrr=108.77&cvrfrr=ET&ctrfrr=SC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Mon, Mar 2 - Tue, Mar 3 ### Full Size Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Chevrolet Malibu](//mediaim.expedia.com/cars/15/e05d24e7-d774-4748-8823-b06bc55f96d7.jpg) #### CA $109 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=94.49&tprfrr=108.77&cvrfrr=ET&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Wed, Mar 4 - Thu, Mar 5 ### Premium Pickup Regular Cab Ford F150 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Ford F150](//mediaim.expedia.com/cars/15/1e5e8f76-968e-45c6-ab89-0f1953159e8b.jpg) #### CA $113 total found 17 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=04/03/2026&date2=05/03/2026&pprfrr=101.39&tprfrr=112.82&cvrfrr=ET&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Wed, Mar 4 - Thu, Mar 5 ### Luxury Audi A4 or BMW 3 Series or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Audi A4 or BMW 3 Series](//mediaim.expedia.com/cars/15/47afa9c2-c072-412e-862a-e2fc10bdcff1.jpg) #### CA $116 total found 17 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=04/03/2026&date2=05/03/2026&pprfrr=101.39&tprfrr=116.48&cvrfrr=ET&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Wed, Mar 4 - Thu, Mar 5 ### Mini Van Chrysler Pacifica or similar - 7 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Chrysler Pacifica](//mediaim.expedia.com/cars/15/4f3d23c1-e9d3-4965-9a7f-67dc72f2e992.jpg) #### CA $121 total found 17 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=04/03/2026&date2=05/03/2026&pprfrr=105.57&tprfrr=121.14&cvrfrr=ET&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Mon, Mar 2 - Tue, Mar 3 ### Oversize SUV Lincoln Navigator L Jeep Grand Wagoneer L or similar - 7 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Lincoln Navigator L Jeep Grand Wagoneer L](//mediaim.expedia.com/cars/15/8ec48088-7b14-4511-9f7f-d085a5b93e47.jpg) #### CA $156 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=136.94&tprfrr=156.11&cvrfrr=ET&ctrfrr=OF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Mon, Mar 2 - Tue, Mar 3 ### Special Van Mercedes Benz Sprinter Van or similar - 12 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Mercedes Benz Sprinter Van](//mediaim.expedia.com/cars/15/159913e3-a293-4528-9c4c-bd7f1e4ec969.jpg) #### CA $187 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=02/03/2026&date2=03/03/2026&pprfrr=164.31&tprfrr=186.64&cvrfrr=ET&ctrfrr=XV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22van%22]) ### Don't see what you're looking for? See all car rentals in Chestertown [View all cars](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20Maryland,%20United%20States%20of%20America&dpln=7215&date1=05/03/2026&date2=07/03/2026&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 2 days. 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=CTG_SPRING_PROMO_7215) ## 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 88 kilometres 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 97 kilometres from Chestertown. > - Battery Park is located 241 kilometres 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? ## Car Rental Information | Popular car types: | [SUV](https://www.expedia.ca/lp/b/car-rental/suv?rfrr=car.table.SUV), [Full Size](https://www.expedia.ca/lp/b/car-rental/fullsize?rfrr=car.table.FullSize), [Economy](https://www.expedia.ca/lp/b/car-rental/economy?rfrr=car.table.Economy) | | -------------------------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Car suppliers available: | | | Our best deal of the day: | CA $103 | | Our second best deal of the day: | CA $106 | | Our third best deal of the day: | CA $109 | | From the airport to your hotel: | [Airport Transportation](https://www.expedia.ca/ground-transfers?rfrr=car.table.AirportTransportation) | ## Explore a world of travel with Expedia - 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