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Winchester car rentals from $44/day

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Car Rental Deals

Cheap car rentals in Winchester

Mitsubishi Mirage car
Mitsubishi Mirage
or similar Small
2
2
4-5
$44/day
View deal
Hyundai Kona car
Hyundai Kona
or similar Small
4
2
2/4
$60/day
View deal
Toyota Corolla car
Toyota Corolla
or similar Medium
5
3
2/4
$44/day
View deal
Nissan Altima car
Nissan Altima
or similar Large
5
2
4-5
$47/day
View deal
Chrysler Pacifica car
Chrysler Pacifica
or similar Van
5
5
4-5
$88/day
View deal
Mazda CX-90 car
Mazda CX-90
or similar SUV
5
2
4-5
$68/day
View deal
Class Premium Car car
Class Premium Car
or similar Luxury
5
5
4-5
$62/day
View deal
Honda Odyssey car
Honda Odyssey
or similar Van
5
2
4-5
$96/day
View deal
Class Luxury Car car
Class Luxury Car
or similar Luxury
5
5
4-5
$69/day
View deal
Ford F-150 car
Ford F-150
or similar Pickup truck
5
5
2/4
$66/day
View deal
Class Premium SUV car
Class Premium SUV
or similar SUV
5
5
4-5
$77/day
View deal
Chevrolet Equinox car
Chevrolet Equinox
or similar SUV
5
3
4-5
$61/day
View deal
Nissan Rogue car
Nissan Rogue
or similar SUV
5
3
4-5
$63/day
View deal
Audi Q5 car
Audi Q5
or similar SUV
5
5
4-5
$79/day
View deal
Booking Insights

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 90 days before your trip in order to get a below-average price.

What is the most popular rental car in Winchester?

Rentals in the Large category (Toyota Camry or similar) are the most popular option in Winchester, costing $43/day on average. Some users have found deals as low as $38/day.

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

The cheapest month to rent a car in Winchester is December at an average cost of $45/day. July is the most expensive month to rent a car in Winchester when prices are $77/day on average, which tends to be 37% 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

Winchester car rental price comparison by vehicle type

Find the right rental car in Winchester by comparing prices across vehicle types.

Small cars

$31 - $98

All Car Types

$50 - $70

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

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

How much does it cost to rent an SUV in Winchester?

Small car rentals in Winchester typically cost around $53 per day. The best time to book is December, when prices average $31 per day which is about 42% less than the yearly average. Small cars are usually 11% cheaper than the average rental in Winchester, making them ideal for budget-conscious travelers.

Medium car rentals in Winchester typically cost around $52 per day. The best time to book is February, when prices average $39 per day which is about 25% less than the yearly average. Medium cars are usually 12% cheaper than the average rental in Winchester, offering a good balance of space and value.

SUV rentals in Winchester typically cost around $67 per day. The best time to book is January, when prices average $44 per day which is about 35% less than the yearly average. SUVs are typically 12% more expensive than the average rental in Winchester, but provide extra space and capability for groups or road trips.

Good to know

Most popular agency

Most popular car type

Average price

Good deal

Dollar
Large
$55/day
$47/day

KAYAK’s top tips for renting a car in Winchester

  • 25% of our users found rental cars in Winchester for $47 or less
  • Large rental cars in Winchester are around 73% 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 $55 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 $45.

  • Which car rental companies are at Blue Grass airport (LEX)?

    The only car rental company onsite at Blue Grass airport is Thrifty.

  • 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 Large car rental cost in Winchester?

    A Large car rental in Winchester costs $43 per day, on average.

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

    A Medium car rental in Winchester costs $158 per day, on average.

  • What is the most popular rental car location in Winchester?

    In Winchester, cars are most frequently rented at Hertz 4000 Terminal Dr Ste 105 (23 miles from city center).

  • 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

 

Enterprise Rent-A-Car

No score available yet

6 locations in Winchester

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 - 12:00

120 E Main St

+1 859 499 3571

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday
Sunday

121 Sand Lake Dr

+1 859 269 9149

Monday08:00 - 18:00
Tuesday08:00 - 18:00
Wednesday08:00 - 18:00
Thursday08:00 - 18:00
Friday08:00 - 18:00
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
Sunday

4139 Lexington Rd

+1 859 987 1554

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday
Sunday

878 Bypass Road

+1 859 744 5500

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday
Sunday

Filters

No reviews available

Arow Enterprises Corp.

No score available yet

One location in Winchester

Locations in Winchester

878 Bypass Road, Winchester

+1 859 744 5500

Monday00:00 - 23:59
Tuesday00:00 - 23:59
Wednesday00:00 - 23:59
Thursday00:00 - 23:59
Friday00:00 - 23:59
Saturday00:00 - 23:59
Sunday00:00 - 23:59

Filters

No reviews available

Dollar

No score available yet

One location in Winchester

Locations in Winchester

2893 Richmond Road Ste 130

+1 859 243 0335

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday09:00 - 12:00

Filters

No reviews available

Hertz

No score available yet

One location in Winchester

Locations in Winchester

2893 Richmond Rd Ste 130

+1 859 243 0335

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday09:00 - 12:00

Filters

Reviews

2.0 Poor

kodaville, Apr 2026

Supplier choice

KAYAK
Seems very deceptive. They didn't have my car when I went for pickup and alternatively offered me another vehicle that was much more expensive. This seems to be a tactic of their of manipulating customers into higher prices who are stressed for time. I ended up walking out of there, walking down the street, and took my business to Enterprise, who took care of me in a matter of 5 minutes. Never going back to Hertz.

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

1 out of 3

Thrifty

No score available yet

One location in Winchester

Locations in Winchester

2893 Richmond Road Ste 130

+1 859 243 0335

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday09:00 - 12:00

Filters

No reviews available

Car rental locations in or near Winchester

Go to map view

More options for your car rental in Winchester

Winchester car rental information

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