Winchester car rentals from $55/day

This price is the cheapest per day rate found by a KAYAK user in the last 48 hours by searching for a car rental in Winchester with a pick-up date of 1/21 and drop-off date of 1/28. Fares are subject to change and may not be available at all agencies or on all dates of rental. Click the price to replicate the search for this deal.

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Car Rental Deals
Booking Insights
Car Rental Deals

Cheap car rentals in Winchester

Discover the best prices for you by selecting your travel dates on KAYAK.
Mitsubishi Mirage car
Mitsubishi Mirage
or similar Small
Passengers count 2 adult passengers
Bags count 2 large bags
Door count 4-5 doors
$55/day
View Deal
Nissan Versa car
Nissan Versa
or similar Small
Passengers count 4 adult passengers
Bags count 2 large bags
Door count 2/4 doors
$55/day
View Deal
Toyota Corolla car
Toyota Corolla
or similar Medium
Passengers count 5 adult passengers
Bags count 3 large bags
Door count 2/4 doors
$57/day
View Deal
Chevrolet Malibu car
Chevrolet Malibu
or similar Large
Passengers count 5 adult passengers
Bags count 2 large bags
Door count 4-5 doors
$60/day
View Deal
Chrysler Pacifica car
Chrysler Pacifica
or similar Van
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 4-5 doors
$68/day
View Deal
Class Full-size SUV car
Class Full-size SUV
or similar SUV
Passengers count 5 adult passengers
Bags count 2 large bags
Door count 4-5 doors
$101/day
View Deal
Nissan Maxima car
Nissan Maxima
or similar Luxury
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 2/4 doors
$74/day
View Deal
Audi A4 car
Audi A4
or similar Luxury
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 4-5 doors
$82/day
View Deal
Ford F-150 car
Ford F-150
or similar Pickup truck
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 2/4 doors
$70/day
View Deal
Class Premium SUV car
Class Premium SUV
or similar SUV
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 4-5 doors
$121/day
View Deal
Class Compact SUV car
Class Compact SUV
or similar SUV
Passengers count 4 adult passengers
Bags count 2 large bags
Door count 4-5 doors
$65/day
View Deal
Nissan Rogue car
Nissan Rogue
or similar SUV
Passengers count 5 adult passengers
Bags count 3 large bags
Door count 4-5 doors
$65/day
View Deal
Audi Q5 car
Audi Q5
or similar SUV
Passengers count 5 adult passengers
Bags count 5 large bags
Door count 4-5 doors
$90/day
View Deal
Best rates found by KAYAK users in the past 48 hours.
Booking Insights

Good to know

Most popular car type

Average price

Good deal

Luxury
$34/day
$31/day

KAYAK’s insights & trends for Winchester car rentals

Check out the latest trends and booking tips to rent a car in Winchester with confidence.

How far in advance should you book a rental car in Winchester?

You should book your rental car in Winchester around 31 days before your trip in order to get a below-average price.

What is the best rental car company in Winchester?

Based on ratings and reviews from real users on KAYAK, the best car rental companies in Winchester are Enterprise Rent-A-Car (0.0, 4 reviews), Arow Enterprises Corp. (0.0), and Dollar (0.0).

Enterprise Rent-A-Car
Enterprise Rent-A-Car
Rated 0.0/10
Arow Enterprises Corp.
Arow Enterprises Corp.
Rated 0.0/10
Dollar
Dollar
Rated 0.0/10
Hertz
Hertz
Rated 0.0/10

What is the most popular rental car in Winchester?

Rentals in the Van category (Chrysler Pacifica or similar) are the most popular option in Winchester, costing $74/day on average. Some users have found deals as low as $74/day.

What is the cheapest month to rent a car in Winchester?

The cheapest month to rent a car in Winchester is February at an average cost of $40/day. June is the most expensive month to rent a car in Winchester when prices are $82/day on average, which tends to be 36% above the yearly average rental price for Winchester.

What rental car company in Winchester has the most locations?

Enterprise Rent-A-Car operates 6 locations in Winchester, more than any other rental company.

Find deals

KAYAK’s top tips for renting a car in Winchester

  • 25% of our users found rental cars in Winchester for $31 or less
  • Medium rental cars in Winchester are around 42% cheaper than other car types, on average

FAQs about renting a car in Winchester

  • How much does it cost to rent a car in Winchester?

    On average a rental car in Winchester costs $34 per day. But prices differ between operators and you can save money through a price comparison of car rental deals from different agencies. The cheapest price for a car rental in Winchester found in the last 2 weeks is $34.

  • How can I find car rentals near me in Winchester?

    Take a look at our extensive car rental location map to find the best rental cars near you.

  • How much does a Luxury car rental cost in Winchester?

    A Luxury car rental in Winchester costs $72 per day, on average.

  • How much does a Medium car rental cost in Winchester?

    A Medium car rental in Winchester costs $42 per day, on average.

  • Should I get insurance when renting a car in Winchester?

    Most car rental providers in Winchester offer insurance but the level of protection can differ substantially. If you're unsure whether to get extra protection for your car rental in Winchester, check out KAYAK's car rental insurance guide.

  • How many car agencies are operating in Winchester?

    KAYAK has deals for you to compare from 2 car rental agencies in Winchester.

  • What do I need to know before booking a car rental in Winchester?

    Finding the right price, understanding the add-ons and staying up to date with policy changes can be a challenge. That’s why KAYAK has produced the ultimate guide to renting a car to help you cut though the jargon and make the right choice for your rental car. Find tips and insights for how to book your rental, what car rental insurance you’ll need, how to deal with a car rental agency and what extra fees to expect (and avoid!).

  • Why should I use KAYAK to rent a car in Winchester?

    KAYAK searches thousands of car rental agencies to provide you with offers from all car rental agencies operating in Winchester so that you can compare car rental rates, reviews and pick-up and drop-off locations to find the best deal for you.

Winchester car rental reviews and directory

 
All ratings and reviews are collected from KAYAK users with a verified car rental booking. Learn how KAYAK collects reviews.

Enterprise Rent-A-Car

No score available yet

6 locations in Winchester

Show locations

Locations in Winchester

1140 Winchester Road

+1 859 281 6446

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00
Sunday09:00 - 13:00

120 E Main St

+1 859 499 3571

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday00:00 - 00:00
Sunday00:00 - 00:00

121 Sand Lake Dr

+1 859 269 9149

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00

2893 Richmond Rd

+1 859 269 9149

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00
Sunday00:00 - 00:00

4139 Lexington Rd

+1 859 987 1554

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday00:00 - 00:00
Sunday00:00 - 00:00

878 Bypass Road

+1 859 744 5500

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday00:00 - 00:00
Sunday00:00 - 00:00

Filters

Reviews

10.0 Wonderful

Anonymous, Apr 2021

KAYAK

Pros:

Staff was great, Pickup was flawless. Vehicle was perfect

Cons:

It would have been nice if the branch we used was open later so we could physically hand the rental back in. We had to drop it off and leave keys in a drop box. Minor issue, though.

2.0 Poor

Anonymous, Apr 2021

KAYAK

Cons:

It would have been nice if they actually had the car I reserved, or any car at all.

4.0 Mediocre

Anonymous, Mar 2021

KAYAK

Pros:

The car was comfortable and easy to drive

Cons:

Booked the car online, but when I arrived to pick my car up, the staff said there were no cars available. Had to wait over an hour for a car. The car also reeked of cigarette smoke. Vincent was friendly, but the rest of the staff was unfriendly and clearly didn’t care about the customers. Would not book at this location again.

1 out of 2

Arow Enterprises Corp.

No score available yet

One location in Winchester

Show locations

Locations in Winchester

878 Bypass Road, Winchester

+1 859 744 5500

Monday00:00 - 00:00
Tuesday00:00 - 00:00
Wednesday00:00 - 00:00
Thursday00:00 - 00:00
Friday00:00 - 00:00
Saturday00:00 - 00:00
Sunday00:00 - 00:00

Filters

No reviews available

Dollar

No score available yet

One location in Winchester

Show locations

Locations in Winchester

2893 Richmond Road Ste 130

+1 859 243 0335

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00

Filters

No reviews available

Hertz

No score available yet

One location in Winchester

Show locations

Locations in Winchester

2893 Richmond Rd Ste 130

+1 859 243 0335

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00

Filters

Reviews

2.0 Poor

William, Jun 2025

Full-size

KAYAK
Hertz refused to honor the one way reservation from Lexington to Chicago. They said they didn’t have enough cars. That failure cost me over $500. They did the same thing to several other customers with one way reservations. One dejected younger customer was practically in tears. The height of irresponsible corporate behavior.

2.0 Poor

Anonymous, Aug 2024

Compact SUV

KAYAK
they did not have a car to fill my reservation. this is the third time that has happened with hertz in the last two months. what the heck is going on

10.0 Wonderful

Anonymous, Jul 2024

Pickup truck

KAYAK
They were friendly, upfront about all info, and straight forward with prices and deposits. The vehicle that I received was in pristine condition. I will rent from them from now on. They have a guaranteed costumer for life.

2.0 Poor

Anonymous, Dec 2023

Compact

KAYAK
Hertz did not have a rental vehicle available for me when I tried to pick up my vehicle. I had to wait 5 days to get a vehicle. That I had a reservation seemed to mean nothing to Hertz. Customer service staff tried to be nice but ultimately I was not helped.

2.0 Poor

Marie, Nov 2023

Compact

KAYAK
Horrible

2.0 Poor

Dana, Nov 2023

Supplier choice

KAYAK
Hertz's reservation system (or kayak?) allows people to continue reserving and confirms their reservation even when they don't have vehicles available. Local representative was nice about it, but still wasn't able to rent a car.

1 out of 5

Thrifty

No score available yet

One location in Winchester

Show locations

Locations in Winchester

2893 Richmond Road Ste 130

+1 859 243 0335

Monday08:00 - 17:30
Tuesday08:00 - 17:30
Wednesday08:00 - 17:30
Thursday08:00 - 17:30
Friday08:00 - 17:30
Saturday09:00 - 13:00

Filters

No reviews available

Car rental locations in or near Winchester

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Everything you need to know for your car rental in Winchester

Winchester car rental information

Pick-up locationWinchester
Car typesSmall, Medium, Large, SUV, Van, Pickup truck, Luxury
Rental locations2
Airport locations0
Popular agenciesEnterprise Rent-A-Car