Title: CA $107 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. Mon, Nov 24 - Tue, Nov 25 ### 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/b3a20aa9-1ab3-4689-9b70-7c5fd16415ec.jpg) #### CA $107 total found 16 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=24/11/2025&date2=25/11/2025&pprfrr=92.42&tprfrr=106.56&cvrfrr=ET&ctrfrr=CC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22compact%22]) Mon, Nov 24 - Tue, Nov 25 ### 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/a78d55c1-3e9a-4cb4-b034-2b5216e15b71.jpg) #### CA $107 total found 16 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=24/11/2025&date2=25/11/2025&pprfrr=92.42&tprfrr=106.56&cvrfrr=ET&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Mon, Nov 24 - Tue, Nov 25 ### 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/15/076c7dcd-a184-4140-a477-ead2904081d6.jpg) #### CA $108 total found 16 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=24/11/2025&date2=25/11/2025&pprfrr=93.68&tprfrr=107.96&cvrfrr=ET&ctrfrr=IC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Fri, Nov 21 - Sat, Nov 22 ### 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/15/29a4dedf-72c1-4b16-8a5b-6708d188d605.jpg) #### CA $107 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=21/11/2025&date2=22/11/2025&pprfrr=95.75&tprfrr=106.8&cvrfrr=ET&ctrfrr=SP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Mon, Nov 24 - Tue, Nov 25 ### 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/15/81ed9c7b-159d-4edd-acb4-faaaecc03d41.jpg) #### CA $115 total found 16 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=24/11/2025&date2=25/11/2025&pprfrr=99.91&tprfrr=114.91&cvrfrr=ET&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Fri, Nov 21 - Sat, Nov 22 ### 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/daf4999e-9107-4b2a-b19e-8b95b9813c09.jpg) #### CA $114 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=21/11/2025&date2=22/11/2025&pprfrr=102.76&tprfrr=114.37&cvrfrr=ET&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Fri, Nov 21 - Sat, Nov 22 ### 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/15/6faf7680-bb19-4d39-a9f3-e21ec8b4551a.jpg) #### CA $122 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=21/11/2025&date2=22/11/2025&pprfrr=106.63&tprfrr=122.39&cvrfrr=ET&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Mon, Nov 24 - Tue, Nov 25 ### 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/15/83e40a45-9d06-4218-b7dc-7e727248eb1d.jpg) #### CA $274 total found 16 hours ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.219768&olon=-76.082720&date1=24/11/2025&date2=25/11/2025&pprfrr=242.73&tprfrr=274.15&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=25/11/2025&date2=27/11/2025&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 16 hours. Prices and availability subject to change. Additional terms may apply. ## Frequently asked questions ### How much is a rental car per day in Chestertown? > Daily rental prices were as low as CA $107 within the past seven days. With rates like this, cruising the streets of Chestertown in your own set of wheels is an affordable and convenient way to visit the sights. ### What happens if I need to cancel my Chestertown car reservation? > Cancelling a prepaid car booking at least six hours before pickup should allow for a total refund. However, this is not always guaranteed. It's a good idea to scan your itinerary and rental agreement. Still can't find the answer? Hop on our [Customer Service Portal](https://www.expedia.ca/service/?langid=1033). ### Where can I go on a road trip from Chestertown? > After you've ticked off the amazing sights in Chestertown, there's plenty more to see in the surrounding region. Grab the keys to a rental car, pack your bags in the trunk and get out on the open road. We've pulled together some drives we're confident you'll love: > > > > - 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? > Browse our huge selection of rental cars, check out customer ratings and compare prices from big-name brands. In a few simple clicks, Expedia will help you find the best deal on your wheels. Got a hotel or flight booking? Add on your Chestertown car rental to save even more. ### How old do you have to be to rent a car in Chestertown? > If you're aged 21 and over, you can rent a car in Chestertown. Be mindful that rental companies will charge an extra fee if you're a young driver, which helps cover the higher damage risk involved. Also, young drivers are often restricted from renting specialty or luxury vehicles. Thoroughly read the terms and conditions before booking so there are no surprises when it's time to collect the keys. ### What do you need to rent a car in Chestertown? > Two things — your driver's licence and a credit card in your name. Many car rental companies will offer you insurance, which is optional. But you may be asked to provide proof of other coverage if you opt out. We recommend checking with your supplier to avoid any problems. ### What is the cheapest car rental in Chestertown? > The two lowest daily rates offered in Chestertown within the past seven days were CA $107 and CA $108. Now that's what we'd call a fantastic deal! These rates were available on Expedia, with a rental starting date within the next year. Prices and availability are subject to change and additional terms apply. ### Can I rent a car for a month or longer in Chestertown? > Yes, which means you won't have to rebook a rental vehicle mid-vacation. Head over to our [long-term car rental deals](https://www.expedia.ca/lp/b/car-hire/long-term) page, enter your travel dates and find a ride that's all yours for however long you need. ### Where can I find a Chestertown car rental if I am younger than 25? > You'll need to look into the age policy of the Chestertown rental suppliers you're interested in. If you're under 25 years of age, be aware that some will charge additional fees. It's better to know this in advance so you can plan your budget accordingly. Each rental car company has its own rules for younger drivers, so do your research. ## 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 $107 | | Our second best deal of the day: | CA $108 | | Our third best deal of the day: | CA $114 | | 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 - Lodging - Flights - Packages - Cars - Vacation Rental - [Apartments in Betterton](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - [Hotels near Betterton Beach](https://www.expedia.ca/Betterton-Beach-Hotels.0-l553248635983992889-0.Travel-Guide-Filter-Hotels) - 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