Title: Cheap Car Hire in Chestertown, USA - Expedia.co.uk [Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Flights to Chestertown](https://expedia.co.uk/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Chestertown Holidays](https://expedia.co.uk/Chestertown.d89045.Holidays-City-Breaks) ![](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Car Rentals in Chestertown, USA ## 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/BEXUK-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 hire - ![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 hire [Learn about One Key](https://www.expedia.co.uk/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 Rental Car Deals in Chestertown \* Price found within the past 6 days. Click for updated prices. ### Economy Chevrolet Spark or similar - 4 people Chestertown, New York, USA ![Chevrolet Spark](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_EC.png) [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20New%20York,%20United%20States%20of%20America&dpln=89045&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22economy%22]) ### Compact Ford Focus or similar - 4 people Chestertown, New York, USA ![Ford Focus](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_CC.png) [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20New%20York,%20United%20States%20of%20America&dpln=89045&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22compact%22]) ### Midsize Toyota Corolla or similar - 5 people Chestertown, New York, USA ![Toyota Corolla](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_IC.png) [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20New%20York,%20United%20States%20of%20America&dpln=89045&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22midsize%22]) ### SUV Jeep Compass or similar - 5 people Chestertown, New York, USA ![Jeep Compass](//images.trvl-media.com/media/content/shared/images/car/Common_90X50/US_SF.png) [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20New%20York,%20United%20States%20of%20America&dpln=89045&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car hire in Chestertown [View all cars](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chestertown,%20New%20York,%20United%20States%20of%20America&dpln=89045&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place) ## Frequently asked questions ### How much is a rental car per day in Chestertown? ### Can I hire a car from Glens Falls, NY (GFL-Floyd Bennett Memorial)? ### What happens if I need to cancel my Chestertown car reservation? ### What types of cars can I rent in Chestertown? ### Where can I go on a road trip from Chestertown? > - Albany is approximately 70 miles from Chestertown. Top-rated tourist spots like The Egg deserve to be high on your list here. > - Your next stop? Springfield, which is around 120 miles away. Naismith Memorial Basketball Hall of Fame is one local hot spot you shouldn't miss. > - Mount Washington State Park is 130 miles from Chestertown and is one of the region's most gorgeous nature spots. Pack a picnic lunch and enjoy the fresh air here. ### How do I find the best car hire deals in Chestertown with Expedia? ### How old do you have to be to hire a car in Chestertown? ### What do you need to rent a car in Chestertown? ### What is the cheapest car hire in Chestertown? ### Can I hire a car for a month or longer in Chestertown? ### Where can I find a Chestertown hire car if I am younger than 25? ### Can I drive in Chestertown with my current driver's license? > - Age restrictions: You need to be 25 or older in many states in order to hire a car, although in some areas allow drivers as young as 21\. We recommend checking local rules and regulations, as well as the hire car website before your trip to understand all the regulations that may apply to you. > - Driving limitations: Be sure to read the fine print before you drive off the lot so you can avoid any unnecessary fees. When hiring a car in the United States, you typically can't cross country borders into Canada or Mexico, drive onto ferries or traverse rough terrain with your hired vehicle. Please read the regulations before booking! ### Why should I rent a Chestertown car with Expedia? ## Car Hire Information | Popular car types: | [SUV](https://www.expedia.co.uk/lp/b/car-rental/suv?rfrr=car.table.SUV), [Full Size](https://www.expedia.co.uk/lp/b/car-rental/fullsize?rfrr=car.table.FullSize), [Economy](https://www.expedia.co.uk/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.co.uk/ground-transfers?rfrr=car.table.AirportTransportation) | ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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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