$39 Car Rental Winchester, MO

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Top Car Deals in Winchester

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

Mon, Sep 1 to Tue, Sep 2

Special

Managers Special or similar
  • 4 people
  • Unlimited mileage
SAINT ANN, USA
Managers Special

$44

includes taxes & fees
$32 per day
found 11 hours ago
Special Managers Special
Sun, Aug 31 to Mon, Sep 1

Standard Elite Special

Ford Mustang Mach-E or similar
  • 5 people
  • Unlimited mileage
ST LOUIS, USA
Ford Mustang Mach-E

$50

includes taxes & fees
$39 per day
found 2 days ago
Standard Elite Special Ford Mustang Mach-E
Sun, Aug 31 to Mon, Sep 1

Economy Special

Managers Special or similar
  • 4 people
  • Unlimited mileage
ST. LOUIS 631343302, USA
Managers Special

$39

includes taxes & fees
$39 per day
found 2 days ago
Economy Special Managers Special
Sun, Aug 31 to Mon, Sep 1

Compact

Ford Focus or similar
  • 5 people
  • Unlimited mileage
ST. LOUIS 631343302, USA
Ford Focus

$41

includes taxes & fees
$41 per day
found 2 days ago
Compact Ford Focus
Sun, Aug 31 to Mon, Sep 1

Midsize

Mazda 3 4-door or similar
  • 5 people
  • Unlimited mileage
ST. LOUIS 631343302, USA
Mazda 3 4-door

$43

includes taxes & fees
$43 per day
found 2 days ago
Midsize Mazda 3 4-door
Sun, Aug 31 to Mon, Sep 1

Fullsize

Chevrolet Malibu or similar
  • 5 people
  • Unlimited mileage
ST. LOUIS 631343302, USA
Chevrolet Malibu

$44

includes taxes & fees
$44 per day
found 2 days ago
Fullsize Chevrolet Malibu
Sun, Aug 31 to Mon, Sep 1

Standard

Volkswagen Jetta or similar
  • 5 people
  • Unlimited mileage
Saint Louis, Missouri, USA
Volkswagen Jetta

$57

includes taxes & fees
$45 per day
found 2 days ago
Standard Volkswagen Jetta
Sun, Aug 31 to Mon, Sep 1

Midsize Elite

Tesla Short Range Model 3 or similar
  • 5 people
  • Unlimited mileage
ST LOUIS, USA
Tesla Short Range Model 3

$60

includes taxes & fees
$47 per day
found 2 days ago
Midsize Elite Tesla Short Range Model 3
Sun, Aug 31 to Mon, Sep 1

Premium

Nissan Maxima or similar
  • 5 people
  • Unlimited mileage
Saint Louis, Missouri, USA
Nissan Maxima

$74

includes taxes & fees
$59 per day
found 2 days ago
Premium Nissan Maxima
Sun, Aug 31 to Mon, Sep 1

Luxury

Audi A4 or BMW 3 Series or similar
  • 5 people
  • Unlimited mileage
SAINT LOUIS, USA
Audi A4 or BMW 3 Series

$127

includes taxes & fees
$102 per day
found 2 days ago
Luxury Audi A4 or BMW 3 Series
Sun, Aug 31 to Mon, Sep 1

Mini Van

Chrysler Pacifica or similar
  • 7 people
  • Unlimited mileage
SAINT LOUIS, USA
Chrysler Pacifica

$130

includes taxes & fees
$105 per day
found 2 days ago
Mini Van Chrysler Pacifica
Fri, Aug 29 to Sat, Aug 30

Premium Elite Crossover

Cadillac XT6 or similar
  • 5 people
  • Unlimited mileage
Saint Louis, Missouri, USA
Cadillac XT6

$167

includes taxes & fees
$135 per day
found 10 hours ago
Premium Elite Crossover Cadillac XT6

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Lowest prices found within the past 11 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is a rental car per day in Winchester?
Exploring Winchester doesn't have to cost an arm and a leg, with daily car rental prices starting at just $39 within the past seven days.
What happens if I need to cancel my Winchester car reservation?
Our Customer Service Portal has all the details about this. In the majority of cases, total refunds are available if a prepaid rental is canceled more than six hours prior to the arranged pickup time. Be sure to read your policy to double-check if there are any exclusions.
Where can I go on a road trip from Winchester?
There's so much to do in Winchester, but venture farther afield and you'll find more sightseeing magic. Grab a set of wheels and you can discover the surrounding region at your leisure. Add these fantastic drives to your travel schedule:

  • You'll find Illinois State Fairgrounds and loads more intriguing attractions in Springfield. From Winchester, it's 95 miles away.
  • Located 100 miles away, Columbia is also a hit with wanderers. Be sure to experience Mizzou Arena while you're in town. It's one of the reasons people love visiting this city.
  • Starved Rock State Park is around 210 miles from Winchester and is one of the region's most scenic nature spots. Go for a wander around and enjoy the fresh air.

How do I find the best car rental deals in Winchester with Expedia?
Whatever sort of ride you want, Expedia will help you nab the best deal. Just compare the offers from reliable rental suppliers and select the option that's perfect for you. Want to drive away with even more in your wallet? Combine your Winchester car rental with flight or hotel bookings.
How old do you have to be to rent a car in Winchester?
You need to be at least 21. But there are some age-related requirements to keep in mind before you book your Winchester wheels. If you're a younger driver, many rental outlets will charge an additional daily fee and limit the types of vehicles you're able to rent. The surcharge amount, and which ages it applies to, varies between suppliers. It's a good idea to compare the rules.
What do you need to rent a car in Winchester?
Generally, all you'll need is a current driver's license and a credit card in the same name when collecting your car. Proof of coverage may also be required if you decide to opt out of the company's insurance policy. These requirements may differ between rental companies, so it's wise to check while booking.
What is the cheapest car rental in Winchester?
The two cheapest daily prices recorded in Winchester within the past seven days were $39 and $41. How's that for an awesome deal? 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?
Head to our long-term car rental deals page, enter your preferences and then book your perfect ride. Whether you're basing yourself in Winchester or road-tripping about, Expedia will help you find a long-term rental at an amazing rate.
Where can I find a Winchester car rental if I am younger than 25?
Age policies differ between rental suppliers, so be prepared to do a little research. Managed to find a Winchester supplier that does rent to drivers under 25? That's great! Just be aware that extra fees often apply to drivers between the ages of 21 and 24. The terms and conditions of each rental car you're looking at should have all the information you need.
What insurance should I choose for my car rental in Winchester?
It's wise to have collision damage protection to safeguard your Winchester car rental against theft, accident damage and vandalism. 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 round-the-clock emergency assistance and a zero-dollar deductible if you need to make a claim. Have your plans changed? If you cancel your insurance before your scheduled pick-up time, you'll receive a complete refund.

Car Rental Information

 
Popular car types
SUV, Full Size, Economy
 
Car suppliers available
 
Our best deal of the day
$39
 
Our second best deal of the day
$41
 
Our third best deal of the day
$43
 
From the airport to your hotel
Airport Transportation
 
From popular domestic and international airports
Airport Car Rentals

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 $39.

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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