Title: Winchester Car Rental, MA - Search & Compare - Expedia.ca​ [Winchester Travel Guide](https://expedia.ca/Winchester.dx175481)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Winchester Vacation Packages](https://expedia.ca/Winchester.d175481.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/175481/b0e1353c-e076-4705-8fac-9f9c6a9d0f94.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Winchester Car Rental ## Search and Compare from Car Companies in Winchester ## 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 Winchester \* Price found within the past 6 days. Click for updated prices. Mon, Feb 9 - Tue, Feb 10 ### Special Mystery Car May Be Gas Hybrid or EV or similar - 4 people - Unlimited mileage ![Payless](//mediaim.expedia.com/cars/logos/ZA.png) East Boston, Massachusetts, USA ![Mystery Car May Be Gas Hybrid or EV](//mediaim.expedia.com/cars/38/d7b6ad49-b889-473b-b264-8d84cd2746b5.jpg) #### CA $133 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368160&olon=-71.029420&date1=09/02/2026&date2=10/02/2026&pprfrr=42.19&tprfrr=133.19&cvrfrr=ZA&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Mon, Feb 9 - Tue, Feb 10 ### Compact SUV Chevrolet Trax or similar - 5 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) East Boston, Massachusetts, USA ![Chevrolet Trax](//mediaim.expedia.com/cars/43/f98ef5dd-f3a4-4f40-b00e-2ca29b49b4f1.jpg) #### CA $44 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.366670&olon=-71.000000&date1=09/02/2026&date2=10/02/2026&pprfrr=43.52&tprfrr=43.52&cvrfrr=ZR&ctrfrr=CF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Mon, Feb 9 - Tue, Feb 10 ### Midsize Open Air All-Terrain Jeep Wrangler or similar - 5 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) East Boston, Massachusetts, USA ![Jeep Wrangler](//mediaim.expedia.com/cars/43/874637df-2814-43e5-82bd-67ce8b219f55.jpg) #### CA $45 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.366670&olon=-71.000000&date1=09/02/2026&date2=10/02/2026&pprfrr=45.06&tprfrr=45.06&cvrfrr=ZR&ctrfrr=IJ&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Mon, Feb 9 - Tue, Feb 10 ### Full Size Toyota Camry or similar - 5 people - Unlimited mileage ![Payless](//mediaim.expedia.com/cars/logos/ZA.png) East Boston, Massachusetts, USA ![Toyota Camry](//mediaim.expedia.com/cars/38/6b2e6671-cf69-4f12-b616-4e1c3ffeb3a0.jpg) #### CA $153 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368160&olon=-71.029420&date1=09/02/2026&date2=10/02/2026&pprfrr=51.72&tprfrr=153.36&cvrfrr=ZA&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Mon, Feb 9 - Tue, Feb 10 ### Standard Volkswagen Jetta or similar - 5 people - Unlimited mileage ![Payless](//mediaim.expedia.com/cars/logos/ZA.png) East Boston, Massachusetts, USA ![Volkswagen Jetta](//mediaim.expedia.com/cars/38/5d54aa1a-dda0-4673-8dde-ce8e6dcc1e5d.jpg) #### CA $153 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368160&olon=-71.029420&date1=09/02/2026&date2=10/02/2026&pprfrr=51.72&tprfrr=153.36&cvrfrr=ZA&ctrfrr=SC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Mon, Feb 9 - Tue, Feb 10 ### Economy Kia Rio or similar - 5 people - Unlimited mileage ![Payless](//mediaim.expedia.com/cars/logos/ZA.png) East Boston, Massachusetts, USA ![Kia Rio](//mediaim.expedia.com/cars/38/76e4000d-8a9a-4613-9c95-3e2fc238c883.jpg) #### CA $159 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368160&olon=-71.029420&date1=09/02/2026&date2=10/02/2026&pprfrr=54.44&tprfrr=159.15&cvrfrr=ZA&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Mon, Feb 9 - Tue, Feb 10 ### Mini Van Chrysler Pacificia or similar - 7 people - Unlimited mileage ![Payless](//mediaim.expedia.com/cars/logos/ZA.png) East Boston, Massachusetts, USA ![Chrysler Pacificia](//mediaim.expedia.com/cars/38/c57091e9-0504-46a0-b282-6c1a734115b3.jpg) #### CA $162 total found 4 days ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368160&olon=-71.029420&date1=09/02/2026&date2=10/02/2026&pprfrr=55.8&tprfrr=162.04&cvrfrr=ZA&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Wed, Feb 11 - Thu, Feb 12 ### Premium Pickup Regular Cab Ford F150 or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) East Boston, Massachusetts, USA ![Ford F150](//mediaim.expedia.com/cars/6/540fb0f7-9b8f-4fbc-93be-7057b591d5a3.jpg) #### CA $174 total found 1 day ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367090&olon=-71.030620&date1=11/02/2026&date2=12/02/2026&pprfrr=66.08&tprfrr=174.48&cvrfrr=AL&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Wed, Feb 11 - Thu, Feb 12 ### Luxury SUV Lincoln Navigator Infiniti QX80 or similar - 7 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) East Boston, Massachusetts, USA ![Lincoln Navigator Infiniti QX80](//mediaim.expedia.com/cars/6/870d87a7-e3e6-45a5-8f94-e50ab5bb87ea.jpg) #### CA $234 total found 1 day ago [](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367090&olon=-71.030620&date1=11/02/2026&date2=12/02/2026&pprfrr=97.51&tprfrr=233.85&cvrfrr=AL&ctrfrr=LF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car rentals in Winchester [View all cars](https://expedia.ca/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Winchester,%20Massachusetts,%20United%20States%20of%20America&dpln=175481&date1=14/02/2026&date2=16/02/2026&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 4 days. Prices and availability subject to change. Additional terms may apply. ## Frequently asked questions ### How much is a rental car per day in Winchester? ### Can I rent a car from Logan Intl. Airport (BOS)? ### What happens if I need to cancel my Winchester car reservation? ### Where can I go on a road trip from Winchester? > - You'll find Roger Williams Park Zoo and countless other amazing sights in Providence. From Winchester, it's around 72 kilometres away. > - Your next pit stop? It has to be Hartford, which is around 153 kilometres away. Mark Twain House & Museum is one local highlight you really shouldn't miss. > - Battery Park is about 306 kilometres from Winchester and is one of the region's most breathtaking nature spots. Go for a wander around and enjoy the fresh air here. ### How do I find the best car rental deals in Winchester with Expedia? ### How old do you have to be to rent a car in Winchester? ### What do you need to rent a car in Winchester? ### What is the cheapest car rental in Winchester? ### Can I rent a car for a month or longer in Winchester? ### Where can I find a Winchester 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 $44 | | Our second best deal of the day: | CA $45 | | Our third best deal of the day: | CA $133 | | 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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