Title: Chester, NY Car Rental - Free Cancellation Options - Expedia.com [Chester Travel Guide](https://expedia.com/Chester.dx6046665)[Hotels in Chester](https://expedia.com/Chester-Hotels.d6046665.Travel-Guide-Hotels)[Flights to Chester](https://expedia.com/Cheap-Flights-To-Chester.d6046665.Travel-Guide-Flights)[Chester Vacation Packages](https://expedia.com/Chester.d6046665.Destination-Travel-Guides) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # $107 Car Rental Chester, NY ## Search and Compare from Car Companies in Chester ## 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 Chester \* Price found within the past 6 days. Click for updated prices. Thu, Feb 12 - Fri, Feb 13 ### Compact Nissan Versa or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Nissan Versa](//mediaim.expedia.com/cars/15/ff633732-993f-496c-adca-36578941b7ef.jpg) #### $107 includes taxes & fees $78 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=78.2&tprfrr=107.35&cvrfrr=ET&ctrfrr=CC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22compact%22]) Thu, Feb 12 - Fri, Feb 13 ### Economy Mitsubishi Mirage or similar - 4 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Mitsubishi Mirage](//mediaim.expedia.com/cars/15/4a52f48d-d2dc-4ad7-9687-2cc291173826.jpg) #### $107 includes taxes & fees $78 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=77.64&tprfrr=106.59&cvrfrr=ET&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Thu, Feb 12 - Fri, Feb 13 ### Midsize Toyota Corolla or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Toyota Corolla](//mediaim.expedia.com/cars/15/c19eacdb-9281-4b68-b6a1-eb473f97e0fa.jpg) #### $109 includes taxes & fees $80 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=79.53&tprfrr=109.18&cvrfrr=ET&ctrfrr=IC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Thu, Feb 12 - Fri, Feb 13 ### Standard Volkswagen Jetta or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Volkswagen Jetta](//mediaim.expedia.com/cars/15/d773ffa5-f1b9-4c32-8a40-92e0d18b71b4.jpg) #### $114 includes taxes & fees $83 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=82.95&tprfrr=113.88&cvrfrr=ET&ctrfrr=SC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Thu, Feb 12 - Fri, Feb 13 ### Fullsize Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Chevrolet Malibu](//mediaim.expedia.com/cars/15/e05d24e7-d774-4748-8823-b06bc55f96d7.jpg) #### $118 includes taxes & fees $86 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=86.11&tprfrr=118.23&cvrfrr=ET&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Thu, Feb 12 - Fri, Feb 13 ### Premium Special Audi A3\_BMW 2 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Audi A3_BMW 2](//mediaim.expedia.com/cars/15/79513703-6692-4d6c-89b0-cb929ac3933a.jpg) #### $120 includes taxes & fees $88 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=87.74&tprfrr=120.46&cvrfrr=ET&ctrfrr=PX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22premium%22]) Thu, Feb 12 - Fri, Feb 13 ### Standard Elite SUV Audi Q3 Cadillac XT4 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Audi Q3 Cadillac XT4](//mediaim.expedia.com/cars/15/95895291-11ad-4efd-992d-8cde251953c7.jpg) #### $135 includes taxes & fees $98 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=98.06&tprfrr=134.63&cvrfrr=ET&ctrfrr=RF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Thu, Feb 12 - Fri, Feb 13 ### Luxury Audi A4 or BMW 3 Series or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Audi A4 or BMW 3 Series](//mediaim.expedia.com/cars/15/67532ee4-598a-4d3c-b56c-a6a9360c4ee1.jpg) #### $161 includes taxes & fees $117 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=116.99&tprfrr=160.61&cvrfrr=ET&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Thu, Feb 12 - Fri, Feb 13 ### Special Vehicle determined upon pick-up Compact or Larger or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![Vehicle determined upon pick-up Compact or Larger](//mediaim.expedia.com/cars/15/77fbbdef-b37b-4d5e-9fcc-e4f98c135660.jpg) #### $161 includes taxes & fees $117 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=117.3&tprfrr=161.04&cvrfrr=ET&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Thu, Feb 12 - Fri, Feb 13 ### Luxury Elite SUV BMW X7 Range Rover Sport or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) New Windsor, New York, USA ![BMW X7 Range Rover Sport](//mediaim.expedia.com/cars/15/0f7163e2-762c-4c07-8c4b-87169fa22655.jpg) #### $342 includes taxes & fees $249 per day found 1 day ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=41.497178&olon=-74.100084&date1=2/12/2026&date2=2/13/2026&pprfrr=249.0&tprfrr=341.85&cvrfrr=ET&ctrfrr=WF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car rentals in Chester [View all cars](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Chester,%20New%20York,%20United%20States%20of%20America&dpln=6046665&date1=2/16/2026&date2=2/18/2026&crfrr=defaultFlex&SearchType=Place) ## Frequently asked questions ### How much is a rental car per day in Chester? ### Can I rent a car from Stewart Intl. Airport (SWF)? ### What happens if I need to cancel my Chester car reservation? ### Where can I go on a road trip from Chester? > - Head to Hartford for a fun-filled sightseeing adventure. About 85 miles from Chester, it has numerous cool attractions such as Mark Twain House & Museum. > - About 95 miles away, Albany is also a favorite with wanderers. Make time to take in The Egg while you're here. It's one of the reasons people love staying a while in this thriving city. > - Plymouth Rock is about 190 miles from Chester and is one of the region's most gorgeous nature spots. Go for a walk around and enjoy the fresh air here. ### How do I find the best car rental deals in Chester with Expedia? ### How old do you have to be to rent a car in Chester? ### What do you need to rent a car in Chester? ### What is the cheapest car rental in Chester? ### Can I rent a car for a month or longer in Chester? ### Where can I find a Chester car rental if I am younger than 25? ### What insurance should I choose for my car rental in Chester? ## 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 | $107 | | Our second best deal of the day | $109 | | Our third best deal of the day | $114 | | 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 Chester ### **Using our Search Wizard** If the deals that are available on our page do not suit your needs, then enter Chester into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Chester and provide you with a list of the cheapest options, with no added fees. ### **Renting a car in Chester** Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Chester. 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 Chester** Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $107. ### **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 - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Castle Fun Center ](https://www.expedia.com/Castle-Fun-Center-Hotels.0-l6209270-0.Travel-Guide-Filter-Hotels) - [Hotels near Museum Village ](https://www.expedia.com/Museum-Village-Hotels.0-l553248621559142200-0.Travel-Guide-Filter-Hotels) - [Hotels near LEGOLAND® New York ](https://www.expedia.com/LEGOLAND-New-York-Hotels.0-l553248635997928006-0.Travel-Guide-Filter-Hotels) - [Hotels near The Rock Sports Complex ](https://www.expedia.com/The-Rock-Sports-Complex-Hotels.0-l553248624556330411-0.Travel-Guide-Filter-Hotels) - [Hotels near Goosepond Mountain State Park ](https://www.expedia.com/Goosepond-Mountain-State-Park-Hotels.0-l553248635974861777-0.Travel-Guide-Filter-Hotels) - 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