Title: Winchester, KY Car Rental - Free Cancellation Options - Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx7876)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d7876.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d7876.Travel-Guide-Flights)[Winchester Vacation Packages](https://expedia.com/Winchester.d7876.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/7876/276db1f8-3da6-41f2-8d63-03ef378c3f6b.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # $53 Car Rental Winchester, KY ## 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. Thu, Apr 2 - Fri, Apr 3 ### Economy Special Managers Special or similar - 4 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) Lexington, Kentucky, USA ![Managers Special](//mediaim.expedia.com/cars/40/399ec6c5-6cf8-48f4-88d9-b1046275cfbf.jpg) #### $53 includes taxes & fees $36 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.033330&olon=-84.600000&date1=4/2/2026&date2=4/3/2026&pprfrr=35.96&tprfrr=53.03&cvrfrr=ZE&ctrfrr=EX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22economy%22]) Thu, Apr 2 - Fri, Apr 3 ### Midsize Mazda 3 4-door or similar - 5 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) Lexington, Kentucky, USA ![Mazda 3 4-door](//mediaim.expedia.com/cars/40/4d18581d-6ea9-41f9-8ee1-b30c8c1d3cfc.jpg) #### $56 includes taxes & fees $38 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.033330&olon=-84.600000&date1=4/2/2026&date2=4/3/2026&pprfrr=38.38&tprfrr=56.03&cvrfrr=ZE&ctrfrr=IC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22midsize%22]) Thu, Apr 2 - Fri, Apr 3 ### Compact Ford Focus or similar - 5 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) LEXINGTON, USA ![Ford Focus](//mediaim.expedia.com/cars/40/b0b0d176-5217-4b23-9e8d-d49ee10835ec.jpg) #### $56 includes taxes & fees $38 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.033330&olon=-84.600000&date1=4/2/2026&date2=4/3/2026&pprfrr=38.37&tprfrr=56.01&cvrfrr=ZE&ctrfrr=CC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22compact%22]) Thu, Apr 2 - Fri, Apr 3 ### Special Managers Special or similar - 4 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) Lexington, Kentucky, USA ![Managers Special](//mediaim.expedia.com/cars/43/eb66feb7-951f-4cc5-bc22-f50d5dc5457e.jpg) #### $56 includes taxes & fees $38 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.037900&olon=-84.598820&date1=4/2/2026&date2=4/3/2026&pprfrr=38.27&tprfrr=56.17&cvrfrr=ZR&ctrfrr=XX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22other%22]) Thu, Apr 2 - Fri, Apr 3 ### Fullsize Chevrolet Malibu or similar - 5 people - Unlimited mileage ![Hertz](//mediaim.expedia.com/cars/logos/ZE.png) Lexington, Kentucky, USA ![Chevrolet Malibu](//mediaim.expedia.com/cars/40/1290a4c0-23ef-46ad-b34d-e3f26aab3b6c.jpg) #### $61 includes taxes & fees $42 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.033330&olon=-84.600000&date1=4/2/2026&date2=4/3/2026&pprfrr=42.16&tprfrr=60.73&cvrfrr=ZE&ctrfrr=FC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Thu, Apr 2 - Fri, Apr 3 ### Standard Chevrolet Cruze or similar - 5 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) LEXINGTON, USA ![Chevrolet Cruze](//mediaim.expedia.com/cars/43/428f5fd5-c16a-45ea-83fa-3c6a0e647b4c.jpg) #### $62 includes taxes & fees $43 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.037900&olon=-84.598820&date1=4/2/2026&date2=4/3/2026&pprfrr=42.99&tprfrr=62.05&cvrfrr=ZR&ctrfrr=SC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22standard%22]) Mon, Mar 30 - Tue, Mar 31 ### Mini Van Chrysler Pacifica or similar - 7 people - Unlimited mileage ![Dollar](//mediaim.expedia.com/cars/logos/ZR.png) LEXINGTON, USA ![Chrysler Pacifica](//mediaim.expedia.com/cars/43/9c129e79-2a68-4e58-97b3-110d1119e59c.jpg) #### $79 includes taxes & fees $57 per day found 18 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.037900&olon=-84.598820&date1=3/30/2026&date2=3/31/2026&pprfrr=56.73&tprfrr=79.14&cvrfrr=ZR&ctrfrr=MV&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22minivan%22]) Thu, Apr 2 - Fri, Apr 3 ### Premium Pickup Regular Cab Ford F150 or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Lexington, Kentucky, USA ![Ford F150](//mediaim.expedia.com/cars/6/b9f0687c-ec07-4124-8b53-27941227757b.jpg) #### $96 includes taxes & fees $72 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.038160&olon=-84.599080&date1=4/2/2026&date2=4/3/2026&pprfrr=72.08&tprfrr=96.37&cvrfrr=AL&ctrfrr=PP&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22pickup%22]) Thu, Apr 2 - Fri, Apr 3 ### Fullsize Elite Special Audi A5 Sportback or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Lexington, Kentucky, USA ![Audi A5 Sportback](//mediaim.expedia.com/cars/6/1aa75581-58c2-46d7-a512-00053c87d3b2.jpg) #### $113 includes taxes & fees $86 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.038160&olon=-84.599080&date1=4/2/2026&date2=4/3/2026&pprfrr=85.77&tprfrr=113.32&cvrfrr=AL&ctrfrr=GX&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22fullsize%22]) Mon, Mar 30 - Tue, Mar 31 ### Standard Elite SUV Ford Explorer or similar - 7 people - Unlimited mileage ![Budget](//mediaim.expedia.com/cars/logos/ZD.png) Lexington, Kentucky, USA ![Ford Explorer](//mediaim.expedia.com/cars/39/0117d125-955b-455f-87f1-0c60b7d7c1bc.jpg) #### $104 includes taxes & fees $90 per day found 18 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.037870&olon=-84.517140&date1=3/30/2026&date2=3/31/2026&pprfrr=89.99&tprfrr=103.98&cvrfrr=ZD&ctrfrr=RF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Thu, Apr 2 - Fri, Apr 3 ### Premium Elite SUV Audi Q5 or similar - 5 people - Unlimited mileage ![Alamo](//mediaim.expedia.com/cars/logos/AL.png) Lexington, Kentucky, USA ![Audi Q5](//mediaim.expedia.com/cars/6/022979dc-c3d4-466e-a9e1-c39e19c83003.jpg) #### $130 includes taxes & fees $99 per day found 2 days ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=38.038160&olon=-84.599080&date1=4/2/2026&date2=4/3/2026&pprfrr=98.85&tprfrr=129.5&cvrfrr=AL&ctrfrr=UF&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22suv%22]) Mon, Mar 30 - Tue, Mar 31 ### Luxury Audi A4 or BMW 3 Series or similar - 5 people - Unlimited mileage ![Enterprise](//mediaim.expedia.com/cars/logos/ET.png) LEXINGTON, USA ![Audi A4 or BMW 3 Series](//mediaim.expedia.com/cars/15/fe20fe1c-875d-483e-a16e-270dfa00a74e.jpg) #### $114 includes taxes & fees $101 per day found 18 hours ago [](https://expedia.com/carsearch?paandi=true&fdrp=1&styp=2&dagv=1&subm=1&olat=37.998400&olon=-84.445000&date1=3/30/2026&date2=3/31/2026&pprfrr=100.88&tprfrr=113.94&cvrfrr=ET&ctrfrr=LC&crfrr=pricefeedResponseFlex&SearchType=Place&selCC=[%22luxury%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,%20Kentucky,%20United%20States%20of%20America&dpln=7876&date1=4/3/2026&date2=4/5/2026&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 rent a car from Blue Grass Airport (LEX)? ### What happens if I need to cancel my Winchester car reservation? ### Where can I go on a road trip from Winchester? > - Louisville is approximately 90 miles from Winchester. Popular tourist attractions like Churchill Downs deserve a place on your must-see list while you're in town. > - Roughly 80 miles away, Cincinnati is also a favorite with wanderers. Set aside time to experience Great American Ball Park while you're in town. It's one of the reasons people love visiting this city. > - Biltmore Estate is 190 miles from Winchester and is one of the region's most gorgeous nature spots. Go for a walk around 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 | $53 | | Our second best deal of the day | $56 | | Our third best deal of the day | $61 | | 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 $53. ### **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 - [Hotels near Bluegrass Heritage Museum ](https://www.expedia.com/Bluegrass-Heritage-Museum-Hotels.0-l553248621561880736-0.Travel-Guide-Filter-Hotels) - [Hotels near Community Park ](https://www.expedia.com/Community-Park-Hotels.0-l6263168-0.Travel-Guide-Filter-Hotels) - [Hotels near Clark Regional Medical Center ](https://www.expedia.com/Clark-Regional-Medical-Center-Hotels.0-l6263150-0.Travel-Guide-Filter-Hotels) - [Hotels near Lykins Park ](https://www.expedia.com/Lykins-Park-Hotels.0-l6263146-0.Travel-Guide-Filter-Hotels) - [Hotels near Southwind Golf Course ](https://www.expedia.com/Southwind-Golf-Course-Hotels.0-l6263194-0.Travel-Guide-Filter-Hotels) - [Hotels near Cassell Creek Golf Course ](https://www.expedia.com/Cassell-Creek-Golf-Course-Hotels.0-l6263137-0.Travel-Guide-Filter-Hotels) - 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[Rv Parks in Mount Sterling ](https://www.expedia.com/Mount-Sterling-RV-Parks.d8990-aaRVParks.Travel-Guide-Accommodation) - [Hotels with smoking rooms in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Hotels-With-Smoking-Rooms.0-0-d8990-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Mount Sterling ](https://www.expedia.com/4Star-Mount-Sterling-Hotels.s40-0-d8990.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Luxury-Hotel.0-0-d8990-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [B&B in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Bed-And-Breakfast.d8990-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Motels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Motels.d8990-aaMotels.Travel-Guide-Accommodation) - [3 Star Hotels in Mount Sterling ](https://www.expedia.com/3Star-Mount-Sterling-Hotels.s30-0-d8990.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Marriott-Hotels-Resorts.0-0-d8990--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Hilton-Hotels.0-0-d8990--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Gym in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Hotels-With-Fitness-Center.0-0-d8990-tHotelswithFitnessCenter.Travel-Guide-Filter-Hotels) - [Apartments in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Apartments.d8990-aaApartments.Travel-Guide-Accommodation) - [Cottages in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Cottages.d8990-aaCottages.Travel-Guide-Accommodation) - [Hotels with an Outdoor Pool in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Hotels-With-Outdoor-Pool.0-0-d8990-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - [Family Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Family-Hotel.0-0-d8990-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Connecting Rooms in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Hotels-With-Adjoining-Rooms.0-0-d8990-tHotelswithAdjoiningRooms.Travel-Guide-Filter-Hotels) - [Extended Stay Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Extended-Stay-Hotels.0-0-d8990-tExtendedStayHotels.Travel-Guide-Filter-Hotels) - [Red Roof Inn Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Red-Roof-Inn.0-0-d8990--bRedRoofInn.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Best-Western.0-0-d8990--bBestWestern.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Wedding-Hotels.0-0-d8990-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Hotels-Spa-Hotel.0-0-d8990-tSpaHotel.Travel-Guide-Filter-Hotels) - [Condo Rentals in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Condos.d8990-aaCondos.Travel-Guide-Accommodation) - [Farmstay in Mount Sterling ](https://www.expedia.com/Mount-Sterling-Agritourism.d8990-aaAgritourism.Travel-Guide-Accommodation) - 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