Title: Cheap Car Hire in Winchester, USA - Expedia.co.uk [Winchester Travel Guide](https://expedia.co.uk/Winchester.dx175481)[Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Winchester Holidays](https://expedia.co.uk/Winchester.d175481.Holidays-City-Breaks) ![](https://images.trvl-media.com/place/175481/b0e1353c-e076-4705-8fac-9f9c6a9d0f94.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Car Rentals in Winchester, USA ## 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/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 Winchester \* Price found within the past 6 days. Click for updated prices. Sat, 7 Feb - Sun, 8 Feb ### Special Managers Special or similar - 4 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) #### Pick-up location 100 Tomahawk Dr, East, Boston, Massachusetts, USA 7.96 mi from Winchester city centre ![Managers Special](//mediaim.expedia.com/cars/43/eb66feb7-951f-4cc5-bc22-f50d5dc5457e.jpg) #### £29 total found 10 hours ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=07/02/2026&date2=08/02/2026&pprfrr=null&tprfrr=29.44&cvrfrr=ZR&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Thu, 5 Feb - Fri, 6 Feb ### Standard Chevrolet Cruze or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Chevrolet Cruze](//mediaim.expedia.com/cars/45/90787807-9af7-4241-9b58-a7795543b073.jpg) #### £30 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=29.97&cvrfrr=ZT&ctrfrr=SC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Thu, 5 Feb - Fri, 6 Feb ### Economy Chevrolet Spark or similar - 4 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Chevrolet Spark](//mediaim.expedia.com/cars/45/72c58f0a-a81a-48e3-befa-2ee0943c5166.jpg) #### £30 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=29.93&cvrfrr=ZT&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Thu, 5 Feb - Fri, 6 Feb ### Compact Nissan Versa or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Nissan Versa](//mediaim.expedia.com/cars/45/c105beb9-a46e-424d-b2bf-e837f1415a74.jpg) #### £30 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=30.22&cvrfrr=ZT&ctrfrr=CC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22compact%22]) Thu, 5 Feb - Fri, 6 Feb ### Midsize Toyota Corolla or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Toyota Corolla](//mediaim.expedia.com/cars/45/c796a291-1b50-4fea-857c-e1fd68646d08.jpg) #### £31 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=30.65&cvrfrr=ZT&ctrfrr=IC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Thu, 5 Feb - Fri, 6 Feb ### Full Size Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Chevrolet Malibu](//mediaim.expedia.com/cars/45/5589fccc-a42b-4acc-8092-e77ea23a122e.jpg) #### £32 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=31.65&cvrfrr=ZT&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Thu, 5 Feb - Fri, 6 Feb ### Full Size Elite Pickup Regular Cab Ram 2500 Crew or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Ram 2500 Crew](//mediaim.expedia.com/cars/45/b3514c8b-f726-43d3-99fe-35c382ed1003.jpg) #### £36 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=36.09&cvrfrr=ZT&ctrfrr=GP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Sat, 7 Feb - Sun, 8 Feb ### Standard Elite SUV Ford Explorer or similar - 5 people - Unlimited mileage ![Avis](//mediaim.expedia.com/cars/logos/ZI.png) #### Pick-up location 15 Transportation Way Logan International Airport, Boston, Massachusetts 02128, USA 7.98 mi from Winchester city centre ![Ford Explorer](//mediaim.expedia.com/cars/41/c92cbd55-45b2-4fbe-b152-5ae503cf5057.jpg) #### £57 total found 10 hours ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368333&olon=-71.029722&date1=07/02/2026&date2=08/02/2026&pprfrr=null&tprfrr=56.8&cvrfrr=ZI&ctrfrr=RF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Thu, 5 Feb - Fri, 6 Feb ### Mini Van Chrysler Pacifica or similar - 7 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.96 mi from Winchester city centre ![Chrysler Pacifica](//mediaim.expedia.com/cars/45/465d9c89-1a3c-4baf-a83e-3d676fee5fdd.jpg) #### £58 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.368270&olon=-71.030284&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=58.3&cvrfrr=ZT&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Thu, 5 Feb - Fri, 6 Feb ### Premium Nissan Maxima or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) #### Pick-up location 15 Transportation Way, East Boston, Massachusetts 02128, USA 8.01 mi from Winchester city centre ![Nissan Maxima](//mediaim.expedia.com/cars/6/d7da2389-cdf2-4ff7-ac81-372ee2442fe9.jpg) #### £65 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367090&olon=-71.030620&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=64.96&cvrfrr=AL&ctrfrr=PC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22premium%22]) Thu, 5 Feb - Fri, 6 Feb ### Luxury Audi A4 or BMW 3 Series or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) #### Pick-up location 15 Transportation Way, East Boston, Massachusetts 02128, USA 8.01 mi from Winchester city centre ![Audi A4 or BMW 3 Series](//mediaim.expedia.com/cars/6/f84d223e-53e9-443e-bfd1-5b43e349e9be.jpg) #### £65 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367090&olon=-71.030620&date1=05/02/2026&date2=06/02/2026&pprfrr=null&tprfrr=64.96&cvrfrr=AL&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Thu, 5 Feb - Fri, 6 Feb ### Midsize Elite BMW 2 SERIES or similar - 5 people - Unlimited mileage ![Sixt](//mediaim.expedia.com/cars/logos/SX.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.95 mi from Winchester city centre ![BMW 2 SERIES](//mediaim.expedia.com/cars/35/5a089ac0-0650-490c-a6dc-6d2038d003ac.jpg) #### £68 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367560&olon=-71.031680&date1=05/02/2026&date2=06/02/2026&pprfrr=64.12&tprfrr=67.59&cvrfrr=SX&ctrfrr=JC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Thu, 5 Feb - Fri, 6 Feb ### Premium Elite SUV BMW X7 or similar - 7 people - Limited mileage ![Sixt](//mediaim.expedia.com/cars/logos/SX.png) #### Pick-up location 100 Tomahawk Dr, Boston, Massachusetts 02128, USA 7.95 mi from Winchester city centre ![BMW X7](//mediaim.expedia.com/cars/35/a2be9ac8-b512-4a83-a690-96c41d9b0ac9.jpg) #### £111 total found 2 days ago [](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=42.367560&olon=-71.031680&date1=05/02/2026&date2=06/02/2026&pprfrr=104.53&tprfrr=110.53&cvrfrr=SX&ctrfrr=UF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) ### Don't see what you're looking for? See all car hire in Winchester [View all cars](https://expedia.co.uk/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Winchester,%20Massachusetts,%20United%20States%20of%20America&dpln=175481&date1=09/02/2026&date2=11/02/2026&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 2 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 hire a car from Logan Intl. Airport (BOS)? ### What happens if I need to cancel my Winchester car reservation? ### What types of cars can I rent in Winchester? ### Where can I go on a road trip from Winchester? > - You'll discover Yale University and lots more intriguing attractions in New Haven. From Winchester, it's roughly 120 miles away. > - Roughly 45 miles away, Providence is also a hit with wanderers. Be sure to get to Brown University while you're here. It's one of the reasons people love this buzzing city. > - Find your way to Mount Washington State Park to discover some local nature. Pack a picnic to enjoy or just sit and unwind. From Winchester, it's roughly 130 miles away. ### How do I find the best car hire deals in Winchester with Expedia? ### How old do you have to be to hire a car in Winchester? ### What do you need to hire a car in Winchester? ### What is the cheapest car rental in Winchester? ### Can I hire a car for a month or longer in Winchester? ### Where can I find a Winchester hire car if I am younger than 25? ### Can I drive in Winchester with my current driver's license? > - Age restrictions: You must be at least 25 in most states to be able to hire a car, although in some places, the minimum age is 21 years. We recommend checking local rules and regulations, as well as the hire car website before you travel to understand all the regulations that may apply to you. > - Driving limitations: Don't forget to read the fine print before you leave the lot so you can avoid unnecessary fees. When hiring a car in the U.S, you typically can't cross country borders into Canada or Mexico, drive on ferries or traverse off-road areas with a hire car. Please read the regulations before booking! ### Why should I rent a Winchester 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: | £29 | | Our second best deal of the day: | £30 | | Our third best deal of the day: | £31 | | From the airport to your hotel: | [Airport Transportation](https://www.expedia.co.uk/ground-transfers?rfrr=car.table.AirportTransportation) | ## Explore a world of travel with Expedia - 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