$52 Car Rental Winchester, KY

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Top Car Deals in Winchester

* Price found within the past 6 days. Click for updated prices.

Sun, Nov 2 to Mon, Nov 3

Midsize Special

Kia Niro or similar
  • 5 people
  • Unlimited mileage
Lexington, Kentucky, USA
Kia Niro

$55

includes taxes & fees
$46 per day
found 14 hours ago
Midsize Special Kia Niro
Sun, Nov 2 to Mon, Nov 3

Special

Mystery Car May Be Gas Hybrid or EV or similar
  • 4 people
  • Unlimited mileage
Lexington, Kentucky, USA
Mystery Car May Be Gas Hybrid or EV

$55

includes taxes & fees
$46 per day
found 14 hours ago
Special Mystery Car May Be Gas Hybrid or EV
Sun, Nov 2 to Mon, Nov 3

Compact

Kia Soul or similar
  • 5 people
  • Unlimited mileage
Lexington, Kentucky, USA
Kia Soul

$55

includes taxes & fees
$46 per day
found 14 hours ago
Compact Kia Soul
Sun, Nov 2 to Mon, Nov 3

Economy Special

Managers Special or similar
  • 4 people
  • Unlimited mileage
Lexington, Kentucky, USA
Managers Special

$52

includes taxes & fees
$52 per day
found 14 hours ago
Economy Special Managers Special
Sat, Nov 1 to Sun, Nov 2

Standard

Volkswagen Jetta or similar
  • 5 people
  • Unlimited mileage
Richmond, Kentucky, USA
Volkswagen Jetta

$67

includes taxes & fees
$59 per day
found 7 hours ago
Standard Volkswagen Jetta
Sat, Nov 1 to Sun, Nov 2

Fullsize

Chevrolet Malibu or similar
  • 5 people
  • Unlimited mileage
Richmond, Kentucky, USA
Chevrolet Malibu

$69

includes taxes & fees
$61 per day
found 7 hours ago
Fullsize Chevrolet Malibu
Sun, Nov 2 to Mon, Nov 3

Standard Elite SUV

Jeep Grand Cherokee L or similar
  • 7 people
  • Unlimited mileage
Lexington, Kentucky, USA
Jeep Grand Cherokee L

$79

includes taxes & fees
$68 per day
found 14 hours ago
Standard Elite SUV Jeep Grand Cherokee L
Sun, Nov 2 to Mon, Nov 3

Premium

Toyota Crown or similar
  • 5 people
  • Unlimited mileage
Lexington, Kentucky, USA
Toyota Crown

$82

includes taxes & fees
$70 per day
found 14 hours ago
Premium Toyota Crown
Sun, Nov 2 to Mon, Nov 3

Mini Van

Chrysler Pacifica or similar
  • 7 people
  • Unlimited mileage
Lexington, Kentucky, USA
Chrysler Pacifica

$91

includes taxes & fees
$78 per day
found 14 hours ago
Mini Van Chrysler Pacifica
Sun, Nov 2 to Mon, Nov 3

Luxury

Genesis G70 or similar
  • 5 people
  • Unlimited mileage
Lexington, Kentucky, USA
Genesis G70

$92

includes taxes & fees
$79 per day
found 14 hours ago
Luxury Genesis G70
Sun, Nov 2 to Mon, Nov 3

Fullsize Elite Pickup Regular Cab

Ram 2500 Big Horn or similar
  • 5 people
  • Unlimited mileage
Lexington, Kentucky, USA
Ram 2500 Big Horn

$119

includes taxes & fees
$89 per day
found 14 hours ago
Fullsize Elite Pickup Regular Cab Ram 2500 Big Horn
Sat, Nov 1 to Sun, Nov 2

Premium Elite SUV

Audi Q5 or similar
  • 5 people
  • Unlimited mileage
Richmond, Kentucky, USA
Audi Q5

$148

includes taxes & fees
$131 per day
found 7 hours ago
Premium Elite SUV Audi Q5

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Lowest prices found within the past 14 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is a rental car per day in Winchester?
Exciting road trip adventures in Winchester await, with daily car rental rates starting from as little as $52. That's based on prices found within the past seven days.
Can I rent a car from Blue Grass Airport (LEX)?
Land at Blue Grass Airport (LEX) and then head for Enterprise or Dollar, a short commute away. You'll be exploring the sights and sounds of Winchester in your own set of wheels in no time.
What happens if I need to cancel my Winchester car reservation?
Depending on your rental policy, you may be eligible for a refund. Many reservations provide a complete refund if you let us know six hours before the collection time. Got any queries? If you can't find the answer in your confirmation, our Customer Service Portal is always accessible.
Where can I go on a road trip from Winchester?
There are many exciting adventures to be had in Winchester, but head farther afield and you'll find even more magic. Grab a set of wheels and you can wander around the greater area at your leisure. Add these awesome drives to your travel plan:

  • 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?
Getting an awesome deal on your Winchester rental car is a breeze with Expedia. Choose your preferred car class, add some details and compare prices across major suppliers. Why not add flights and hotels to your booking? You'll unlock even bigger savings when you combine your bookings into a package.
How old do you have to be to rent a car in Winchester?
Drivers 21 and above can hit the road in Winchester in a rental car. If you're a young motorist, a daily surcharge applies. You'll generally have fewer car categories to choose from, such as economy and mid-size, and may also have to buy inclusive insurance. Always enter the correct age of the primary driver when booking to find out if any restrictions apply to you.
What do you need to rent a car in Winchester?
Renting a car in Winchester is easy. Generally, all you'll need is your driver's license and a credit card in your name. After selecting your ride, look up the terms and conditions to ensure there are no extra requirements prior to the pickup date.
What is the cheapest car rental in Winchester?
With rental rates beginning at just $52 and $55 per day in Winchester within the past seven days, you'll be cruising off with your own amazing deal in no time. These rates were available on Expedia, with a rental starting date within the next year. Prices and availability are subject to change and additional terms apply.
Can I rent a car for a month or longer in Winchester?
Whether you're planning to stay in Winchester or venture beyond, it's easy to book a long-term rental with Expedia. Enter your trip information and pick-up/drop-off locations and we'll find you amazing long-term car rental deals.
Where can I find a Winchester car rental if I am younger than 25?
If you're a young driver hoping to rent a vehicle in Winchester, it'd be wise to check the terms and conditions of the rental companies you're interested in. Some may rent to drivers under 25, some may not. Surcharges may apply if you're between 21 and 24 years old. To avoid any nasty surprises on pickup, make sure you know what to expect.
What insurance should I choose for my car rental in Winchester?
It's wise to have collision protection to cover your Winchester rental car against theft, vandalism and accident damage. And with Expedia, you can easily add this insurance to your vehicle during the booking process. Providing up to $35,000 in primary coverage, it also offers 24/7 emergency assistance and a zero-dollar deductible should you need to make a claim. Have your plans changed? If you cancel your policy before your scheduled collection time, you'll get a 100 percent refund.

Car Rental Information

 
Popular car types
SUV, Full Size, Economy
 
Car suppliers available
 
Our best deal of the day
$52
 
Our second best deal of the day
$55
 
Our third best deal of the day
$67
 
From the airport to your hotel
Airport Transportation
 
From popular domestic and international airports
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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 $52.

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 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.

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Car classes available from Expedia in 2025

The classes of vehicles available will change depending on your chosen location.

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