Title: CA $89 Car Rental Chestertown, MD - 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/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chestertown Car Rental ## Search and Compare from Car Companies in Chestertown Photo by Patricia Knorr ## 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. Fri, Jan 16 - Sat, Jan 17 ### Compact SUV Hyundai Kona or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Hyundai Kona](//mediaim.expedia.com/cars/15/0360eac2-907b-4adf-be19-122af4e662aa.jpg) #### CA $89 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=76.52&tprfrr=88.79&cvrfrr=ET&ctrfrr=CF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Jan 16 - Sat, Jan 17 ### Midsize SUV Nissan Rogue or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Nissan Rogue](//mediaim.expedia.com/cars/15/385fd8cd-4b25-4f17-a284-e8cf30c59665.jpg) #### CA $97 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=83.48&tprfrr=96.56&cvrfrr=ET&ctrfrr=IF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Jan 16 - Sat, Jan 17 ### Standard Pickup Regular Cab Toyota Tacoma or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Chestertown, Maryland, USA ![Toyota Tacoma](//mediaim.expedia.com/cars/15/ea4e8f3f-5c26-4a3e-9226-60814d643d68.jpg) #### CA $95 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=84.87&tprfrr=95.03&cvrfrr=ET&ctrfrr=SP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Fri, Jan 16 - Sat, Jan 17 ### 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/d4cfe62b-a396-44d6-899b-7a80c1bc334a.jpg) #### CA $101 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=90.43&tprfrr=101.04&cvrfrr=ET&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Fri, Jan 16 - Sat, Jan 17 ### 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/15/125640d5-7f07-4f45-928d-7144ebb5d760.jpg) #### CA $104 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=90.41&tprfrr=104.28&cvrfrr=ET&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Fri, Jan 16 - Sat, Jan 17 ### 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/b4adb645-39ac-4f1a-89ca-c9f1d238314e.jpg) #### CA $110 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=95.97&tprfrr=110.48&cvrfrr=ET&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Fri, Jan 16 - Sat, Jan 17 ### 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/15/68a7029e-a6b5-4623-bf18-738f5d44baae.jpg) #### CA $134 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=116.86&tprfrr=133.77&cvrfrr=ET&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Fri, Jan 16 - Sat, Jan 17 ### 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/e32dcfec-409d-4e94-9afc-b2daeeb666e5.jpg) #### CA $138 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=16/01/2026&date2=17/01/2026&pprfrr=121.03&tprfrr=138.42&cvrfrr=ET&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Tue, Jan 13 - Wed, Jan 14 ### 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/a939d46d-bd8b-4efc-a6b1-c07aed39ddb7.jpg) #### CA $242 total found 19 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=13/01/2026&date2=14/01/2026&pprfrr=214.25&tprfrr=242.36&cvrfrr=ET&ctrfrr=OF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%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=18/01/2026&date2=20/01/2026&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 19 hours. Prices and availability subject to change. Additional terms may apply. ## 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 $89 | | Our second best deal of the day: | CA $95 | | Our third best deal of the day: | CA $97 | | 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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