Title: Winchester, MD Car Rental - Free Cancellation Options - Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx553248635975872164)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d553248635975872164.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d553248635975872164.Travel-Guide-Flights)[Winchester Vacation Packages](https://expedia.com/Winchester.d553248635975872164.Destination-Travel-Guides) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_car.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # $72 Car Rental Winchester, MD ## Search and Compare from Car Companies in Winchester ## 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 Winchester \* Price found within the past 6 days. Click for updated prices. Fri, Mar 20 - Sat, Mar 21 ### Compact SUV Chevrolet Trax or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) Baltimore, Maryland, USA ![Chevrolet Trax](//mediaim.expedia.com/cars/45/e5049869-5354-4b79-b9ed-1c3a5a8f0f87.jpg) #### $72 includes taxes & fees $50 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176961&olon=-76.705467&date1=3/20/2026&date2=3/21/2026&pprfrr=49.99&tprfrr=72.27&cvrfrr=ZT&ctrfrr=CF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Mar 20 - Sat, Mar 21 ### Midsize SUV Nissan Rogue or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) Baltimore, Maryland, USA ![Nissan Rogue](//mediaim.expedia.com/cars/45/1be06a2c-db8d-49a8-8f4f-cb4db24d9990.jpg) #### $76 includes taxes & fees $53 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176961&olon=-76.705467&date1=3/20/2026&date2=3/21/2026&pprfrr=52.83&tprfrr=75.79&cvrfrr=ZT&ctrfrr=IF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Mar 20 - Sat, Mar 21 ### Special Managers EV-Special or similar - 4 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) Hanover, District of Columbia, USA ![Managers EV-Special](//mediaim.expedia.com/cars/43/aff273ad-1da7-4455-b680-e3518b380cc6.jpg) #### $81 includes taxes & fees $57 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/20/2026&date2=3/21/2026&pprfrr=57.27&tprfrr=81.28&cvrfrr=ZR&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Fri, Mar 20 - Sat, Mar 21 ### Standard SUV Chevrolet Equinox or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) Baltimore, Maryland, USA ![Chevrolet Equinox](//mediaim.expedia.com/cars/45/74679cb4-c978-4a24-8de4-09fbd1976784.jpg) #### $81 includes taxes & fees $57 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176961&olon=-76.705467&date1=3/20/2026&date2=3/21/2026&pprfrr=57.18&tprfrr=81.17&cvrfrr=ZT&ctrfrr=SF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Sun, Mar 22 - Mon, Mar 23 ### Compact Elite Crossover Mercedes-Benz GLA 250 AMG or similar - 5 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) Hanover, District of Columbia, USA ![Mercedes-Benz GLA 250 AMG](//mediaim.expedia.com/cars/43/49bd1887-7d3d-496a-b816-80370ced8d30.jpg) #### $82 includes taxes & fees $58 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/22/2026&date2=3/23/2026&pprfrr=57.95&tprfrr=82.13&cvrfrr=ZR&ctrfrr=DG&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Sun, Mar 22 - Mon, Mar 23 ### Midsize Elite SUV Infiniti QX50 or similar - 5 people - Unlimited mileage ![Thrifty](//mediaim.expedia.com/cars/logos/ZT.png) Baltimore, Maryland, USA ![Infiniti QX50](//mediaim.expedia.com/cars/45/2f3a197a-2c98-4dcb-8451-9e4fd46067a2.jpg) #### $83 includes taxes & fees $59 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176961&olon=-76.705467&date1=3/22/2026&date2=3/23/2026&pprfrr=58.75&tprfrr=83.12&cvrfrr=ZT&ctrfrr=JF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Fri, Mar 20 - Sat, Mar 21 ### Economy Chevrolet Spark or similar - 4 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) Hanover, District of Columbia, USA ![Chevrolet Spark](//mediaim.expedia.com/cars/43/b709c353-edf9-46a5-98da-f1197c7af6eb.jpg) #### $84 includes taxes & fees $59 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/20/2026&date2=3/21/2026&pprfrr=59.38&tprfrr=83.9&cvrfrr=ZR&ctrfrr=EC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Fri, Mar 20 - Sat, Mar 21 ### Fullsize Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) Baltimore, Maryland, USA ![Chevrolet Malibu](//mediaim.expedia.com/cars/40/1290a4c0-23ef-46ad-b34d-e3f26aab3b6c.jpg) #### $86 includes taxes & fees $61 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.177970&olon=-76.700676&date1=3/20/2026&date2=3/21/2026&pprfrr=61.39&tprfrr=86.38&cvrfrr=ZE&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Fri, Mar 20 - Sat, Mar 21 ### Standard Elite Special Ford Mustang Mach-E or similar - 5 people - Unlimited mileage ![Budget](//mediaim.expedia.com/cars/logos/ZD.png) Hanover, District of Columbia, USA ![Ford Mustang Mach-E](//mediaim.expedia.com/cars/39/9eb70d2f-e3e7-4e36-9e24-1505e077c35a.jpg) #### $90 includes taxes & fees $63 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/20/2026&date2=3/21/2026&pprfrr=62.99&tprfrr=90.27&cvrfrr=ZD&ctrfrr=RX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Fri, Mar 20 - Sat, Mar 21 ### Premium Pickup Regular Cab Ford F150 or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Baltimore, Maryland, USA ![Ford F150](//mediaim.expedia.com/cars/6/a9d17556-0fbf-437d-906c-b0f1dd727f74.jpg) #### $90 includes taxes & fees $65 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176651&olon=-76.702895&date1=3/20/2026&date2=3/21/2026&pprfrr=65.00&tprfrr=90.37&cvrfrr=AL&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Sun, Mar 22 - Mon, Mar 23 ### Mini Van Chrysler Pacifica or similar - 7 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Baltimore, Maryland, USA ![Chrysler Pacifica](//mediaim.expedia.com/cars/6/a4b38e23-67b6-4c57-a17a-716397b885b0.jpg) #### $107 includes taxes & fees $76 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176651&olon=-76.702895&date1=3/22/2026&date2=3/23/2026&pprfrr=76.21&tprfrr=107.2&cvrfrr=AL&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Sun, Mar 22 - Mon, Mar 23 ### Luxury Elite Genesis G80E or similar - 5 people - Unlimited mileage ![Budget](//mediaim.expedia.com/cars/logos/ZD.png) Hanover, District of Columbia, USA ![Genesis G80E](//mediaim.expedia.com/cars/39/8cfce1f9-4e0c-482d-8c45-0b135c4d0b15.jpg) #### $124 includes taxes & fees $90 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/22/2026&date2=3/23/2026&pprfrr=89.99&tprfrr=123.72&cvrfrr=ZD&ctrfrr=WC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Sun, Mar 22 - Mon, Mar 23 ### Luxury Cadillac CT5 or similar - 5 people - Unlimited mileage ![Avis](//mediaim.expedia.com/cars/logos/ZI.png) Hanover, District of Columbia, USA ![Cadillac CT5](//mediaim.expedia.com/cars/41/2ef8db43-bb39-4347-80f2-087b3a24fdbf.jpg) #### $138 includes taxes & fees $101 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/22/2026&date2=3/23/2026&pprfrr=100.99&tprfrr=137.59&cvrfrr=ZI&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%22]) Fri, Mar 20 - Sat, Mar 21 ### Premium Elite SUV Audi Q5 or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Baltimore, Maryland, USA ![Audi Q5](//mediaim.expedia.com/cars/6/658a9a7e-ff8a-4887-b1d5-b9226b351acc.jpg) #### $142 includes taxes & fees $104 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176651&olon=-76.702895&date1=3/20/2026&date2=3/21/2026&pprfrr=103.99&tprfrr=141.61&cvrfrr=AL&ctrfrr=UF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Sun, Mar 22 - Mon, Mar 23 ### Fullsize Elite Special Audi A5 Sportback or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) Hanover, District of Columbia, USA ![Audi A5 Sportback](//mediaim.expedia.com/cars/15/7a30e750-1a41-4884-85a5-a5b160fb2632.jpg) #### $206 includes taxes & fees $156 per day found 6 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.175280&olon=-76.668050&date1=3/22/2026&date2=3/23/2026&pprfrr=155.71&tprfrr=205.68&cvrfrr=ET&ctrfrr=GX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Wed, Mar 18 - Thu, Mar 19 ### Oversize Van Ford Transit 15 pax mid roof or similar - 15 people - Unlimited mileage ![Nextcar](//mediaim.expedia.com/cars/logos/NC.png) Hanover, District of Columbia, USA ![Ford Transit 15 pax mid roof](//mediaim.expedia.com/cars/1061/e9223dbe-e4f7-4a6a-a696-7aaa5e788fe5.jpg) #### $460 includes taxes & fees $460 per day found 11 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=39.176900&olon=-76.703270&date1=3/18/2026&date2=3/19/2026&pprfrr=460.00&tprfrr=460.0&cvrfrr=NC&ctrfrr=OV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22van%22]) ### Don't see what you're looking for? See all car rentals in Winchester [View all cars](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&locn=Winchester,%20Maryland,%20United%20States%20of%20America&dpln=553248635975872164&date1=3/23/2026&date2=3/25/2026&crfrr=defaultFlex&SearchType=Place) Lowest prices found within the past 6 hours. 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 Wilmington, DE (ILG-New Castle)? ### What happens if I need to cancel my Winchester car reservation? ### Where can I go on a road trip from Winchester? > - You'll discover White House and lots more interesting sights in Washington. From Winchester, it's roughly 80 miles away. > - Why not see everything on offer in Alexandria too? Unmissable sights in this happening city include George Washington Masonic National Memorial. Alexandria is 85 miles from Winchester. > - First Landing State Park is approximately 190 miles from Winchester and is one of the region's most scenic nature spots. Stretch your legs and enjoy the fresh air. ### 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? ### What insurance should I choose for my car rental in Winchester? ## 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 | $72 | | Our second best deal of the day | $76 | | Our third best deal of the day | $81 | | 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 Winchester ### **Using our Search Wizard** If the deals that are available on our page do not suit your needs, then enter Winchester into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Winchester and provide you with a list of the cheapest options, with no added fees. ### **Renting a car in Winchester** Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Winchester. 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 Winchester** Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $72. ### **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) - 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