Winchester Cheap Car Rentals & Car Hire Deals

Compare rent a car rates in Winchester from popular car rental companies

Featured car rental suppliers

Compare from agencies

car supplier logos

Compare car suppliers to unlock big savings, and package your flight, hotel, and car to save even more.

Members save 10% more on select hotels, cars and activities. Sign up.Opens in a new window

Enjoy maximum flexibility with penalty-free cancellation on most car rentals.

Explore Winchester with Cheap Car Rentals and Car Hire Deals

* Price found within the past 60 days. Click for updated prices.

Don't see what you're looking for?

See all car hire in Winchester
View all cars
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

How much is a rental car per day in Winchester?
Unforgettable road trip adventures in Winchester await, with daily car rental rates starting from as low as . That’s based on prices found within the past seven days.
What happens if I need to cancel my Winchester car reservation?
Check through the home policy to be sure, but nearly all homes qualify for a full refund if you let us know a minimum of six hours before collecting the car. There are some exemptions though. Your booking will have more details, or just hop onto our Customer Service Portal.
What types of cars can I rent in Winchester?
The majority of visitors choose to rent economy vehicles in Winchester. Motorists love them because they’re easy on the budget. Plus, their small size makes them ideal for exploring cities, where streets are crowded and parking can be tight. But economy isn’t your only option. Full-size, mid-size and premium cars are up for grabs too. Whether you’re hanging around Winchester or venturing beyond, we’ll have a ride that suits your needs.
Where can I go on a road trip from Winchester?
It’s no secret that Winchester is one of the top holiday destinations in Scott County. But you’ll also find tons of other fantastic spots to explore when you lock in a set of wheels and head out on the open road. Here are some tips to get your escape off to a superb start:

  • You’ll feel the lively spirit of bustling city life as soon as you pull into St. Louis. Some 113 kilometres from Winchester, it’s home to loads of awesome places to visit, like Busch Stadium.
  • Another city that’s a favourite with travellers is Columbia, around 177 kilometres away. University of Missouri is just one of many reasons why people keep coming back to this place.
  • After a long stint behind the wheel, treat yourself to some time out in nature at Skydeck Ledge. It’s roughly 338 kilometres from Winchester.

Why should I rent a Winchester car with Expedia?
There are plenty of reasons to book your home with Expedia. We have suppliers to select from in Winchester, and we’ll make sure you score the best price with our exclusive offers and member prices. Chasing bigger savings? Bundle your car, hotels and flights into a package. The more you book and travel with Expedia, the more benefits you get!
How do I find the best car rental deals in Winchester with Expedia?
Whatever class of ride you’re after, Expedia will help you find the best deal. Just compare the offers from well-known home suppliers and select the option that works for you. Like to drive away with even bigger savings? Combine your Winchester car rental with flight or hotel bookings.
How old do you have to be to rent a car in Winchester?
The minimum age to rent a vehicle in Winchester is 21. A surcharge for young drivers usually applies, so check before booking and factor in any extra costs. There could also be restrictions on the car categories available to young drivers. For instance, some companies will only rent out economy to medium-sized cars to young motorists. Rules may vary between outlets, so read the fine print carefully.
What do you need to rent a car in Winchester?
A valid driver’s license and a credit card in the same name. Opting out of the company’s insurance plan? If that’s the case, you may need proof of other coverage. Requirements can differ between suppliers, so read through your policy.
Can I rent a car for a month or longer in Winchester?
You can, and the terrific news is suppliers often offer lower rates the longer your holiday home term. Scroll through our long-term car rental deals in Winchester and cruise away with an incredible bargain.
Where can I find a Winchester car rental if I am younger than 25?
You’ll need to look into the age policy of the Winchester holiday home suppliers you’re interested in. If you’re under 25 years of age, some will charge additional costs. It’s handy to know about this in advance so you can plan your budget accordingly. Every holiday home car company has its own terms and conditions for younger drivers, so do your research.
Can I drive in Winchester with my current driver's license?
If you don’t possess a driver’s license issued in the U.S, then you may need to apply for an International Driving Permit (IDP) in your home country before starting the home process. If you find that an IDP is part of the requirements to drive in the U.S., know that you’ll also have to show your current valid driver’s license and your passport or other forms of identification. Lastly, the credit card you used to rent the car must match the name on your driver’s license and passport in order to confirm your home. Other things you should know about rental cars in the U.S. Are:

  • Age restrictions: You’ll need to be 25 in many states to rent a car, although in some places, the minimum age is 21 years. We recommend checking state and local regulations, as well as with the rental car company before your trip to understand all the regulations that may apply to you.
  • Driving limitations: Read the fine print before you get behind the wheel so you can avoid unnecessary fees. When renting a car in the U.S, it’s usually prohibited to cross country borders into Mexico or Canada, drive onto ferries or traverse rough terrain with your car rental. Please read the regulations before booking!

Information on Car Rentals

 
Popular Car Rental Types:
Hire a SUV, Economy, Luxury, Full Size
 
Car Rental Suppliers Available:
 
Today's Best Car Rental Offer:
 
Second Best Car Rental Deal:
 
Third Best Car Rental Deal:
 
Airport to hotel transportation:
Airport Transportation