Title: Cheshire Car Rental, MA - Search & Compare - Expedia.ca​ [Cheshire Travel Guide](https://expedia.ca/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Cheshire Car Rental ## Search and Compare from Car Companies in Cheshire ## 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 Cheshire \* Price found within the past 6 days. Click for updated prices. Fri, Feb 20 - Sat, Feb 21 ### Compact SUV Hyundai Kona or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Hyundai Kona](//mediaim.expedia.com/cars/15/4dd239e4-713b-45f9-97ec-dd1012dc7e18.jpg) #### CA $87 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=74.89&tprfrr=87.07&cvrfrr=ET&ctrfrr=CF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Feb 20 - Sat, Feb 21 ### Midsize SUV Nissan Rogue or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Nissan Rogue](//mediaim.expedia.com/cars/15/826365e4-c1f0-4e01-b62c-5ce99794d816.jpg) #### CA $94 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=81.70&tprfrr=94.31&cvrfrr=ET&ctrfrr=IF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Feb 20 - Sat, Feb 21 ### Standard Pickup Regular Cab Toyota Tacoma or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Toyota Tacoma](//mediaim.expedia.com/cars/15/606f5887-9439-4f25-b101-b42a6743190e.jpg) #### CA $96 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=83.06&tprfrr=95.75&cvrfrr=ET&ctrfrr=SP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Fri, Feb 20 - Sat, Feb 21 ### Economy Special Managers Special or similar - 4 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) Pittsfield, Massachusetts, USA ![Managers Special](//mediaim.expedia.com/cars/40/399ec6c5-6cf8-48f4-88d9-b1046275cfbf.jpg) #### CA $100 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.467390&olon=-73.204550&date1=20/02/2026&date2=21/02/2026&pprfrr=83.05&tprfrr=99.95&cvrfrr=ZE&ctrfrr=EX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Fri, Feb 20 - Sat, Feb 21 ### Premium Pickup Regular Cab Ford F150 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Ford F150](//mediaim.expedia.com/cars/15/1e5e8f76-968e-45c6-ab89-0f1953159e8b.jpg) #### CA $102 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=88.51&tprfrr=101.54&cvrfrr=ET&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Fri, Feb 20 - Sat, Feb 21 ### Special Vehicle determined upon pick-up Compact or Larger or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Vehicle determined upon pick-up Compact or Larger](//mediaim.expedia.com/cars/15/77fbbdef-b37b-4d5e-9fcc-e4f98c135660.jpg) #### CA $116 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=102.10&tprfrr=115.98&cvrfrr=ET&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Fri, Feb 20 - Sat, Feb 21 ### Full Size Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Chevrolet Malibu](//mediaim.expedia.com/cars/15/e05d24e7-d774-4748-8823-b06bc55f96d7.jpg) #### CA $116 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=102.10&tprfrr=115.98&cvrfrr=ET&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Fri, Feb 20 - Sat, Feb 21 ### Mini Van Chrysler Pacifica or similar - 7 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Chrysler Pacifica](//mediaim.expedia.com/cars/15/fcd9733e-9e1f-440b-954a-db8ea8e9b913.jpg) #### CA $116 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=102.10&tprfrr=115.98&cvrfrr=ET&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Fri, Feb 20 - Sat, Feb 21 ### Luxury Audi A4 or BMW 3 Series or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Audi A4 or BMW 3 Series](//mediaim.expedia.com/cars/15/67532ee4-598a-4d3c-b56c-a6a9360c4ee1.jpg) #### CA $133 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=118.45&tprfrr=133.35&cvrfrr=ET&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Fri, Feb 20 - Sat, Feb 21 ### Standard Elite SUV Audi Q3 Cadillac XT4 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Audi Q3 Cadillac XT4](//mediaim.expedia.com/cars/15/95895291-11ad-4efd-992d-8cde251953c7.jpg) #### CA $140 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=124.31&tprfrr=139.57&cvrfrr=ET&ctrfrr=RF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Feb 20 - Sat, Feb 21 ### Premium Elite Special BMW 5 Series Audi A6 or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![BMW 5 Series Audi A6](//mediaim.expedia.com/cars/15/a93707e4-1187-4067-a36b-5b7b2e6ff37a.jpg) #### CA $149 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=132.75&tprfrr=148.55&cvrfrr=ET&ctrfrr=UX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22premium%22]) Fri, Feb 20 - Sat, Feb 21 ### Luxury Elite SUV BMW X7 Range Rover Sport or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![BMW X7 Range Rover Sport](//mediaim.expedia.com/cars/15/0f7163e2-762c-4c07-8c4b-87169fa22655.jpg) #### CA $163 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=146.37&tprfrr=163.01&cvrfrr=ET&ctrfrr=WF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Feb 20 - Sat, Feb 21 ### Oversize SUV Lincoln Navigator L Jeep Grand Wagoneer L or similar - 7 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Pittsfield, Massachusetts, USA ![Lincoln Navigator L Jeep Grand Wagoneer L](//mediaim.expedia.com/cars/15/8ec48088-7b14-4511-9f7f-d085a5b93e47.jpg) #### CA $169 total found 2 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.447410&olon=-73.243460&date1=20/02/2026&date2=21/02/2026&pprfrr=152.22&tprfrr=169.23&cvrfrr=ET&ctrfrr=OF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car rentals in Cheshire [View all cars](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Cheshire,%20Massachusetts,%20United%20States%20of%20America&dpln=6005398&date1=23/02/2026&date2=25/02/2026&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_6005398) ## Frequently asked questions ### How much is a rental car per day in Cheshire? ### What happens if I need to cancel my Cheshire car reservation? ### Where can I go on a road trip from Cheshire? > - Providence is about 161 kilometres from Cheshire. Renowned tourist attractions like Roger Williams Park Zoo deserve to be at the top of your list here. > - About 97 kilometres away, Hartford is also popular with travellers. Make time to take in Mark Twain House & Museum while you're in town. It's one of the reasons people love staying a while in this buzzing city. > - Get out into the outdoors and appreciate the serenity at Plymouth Rock. You'll find it approximately 209 kilometres from Cheshire. ### How do I find the best car rental deals in Cheshire with Expedia? ### How old do you have to be to rent a car in Cheshire? ### What do you need to rent a car in Cheshire? ### What is the cheapest car rental in Cheshire? ### Can I rent a car for a month or longer in Cheshire? ### Where can I find a Cheshire 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 $87 | | Our second best deal of the day: | CA $94 | | Our third best deal of the day: | CA $96 | | From the airport to your hotel: | [Airport Transportation](https://www.expedia.ca/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 and earn double points when you book on 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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