Cheshire car rentals from $45/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 Cheshire with a pick-up date of 11/24 and drop-off date of 12/1. 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.

KAYAK compares hundreds of rental car sites at once for car rental deals in Cheshire, Connecticut

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Car Rental Deals
Booking Insights
Car Rental Deals

Cheap car rentals in Cheshire

Discover the best prices for you by selecting your travel dates on KAYAK.
Mitsubishi Mirage car
Mitsubishi Mirage
or similar Small
2
2
4-5
$45/day
Toyota Corolla car
Toyota Corolla
or similar Medium
5
3
2/4
$45/day
Volkswagen Jetta car
Volkswagen Jetta
or similar Medium
5
3
2/4
$50/day
Chevrolet Malibu car
Chevrolet Malibu
or similar Large
5
2
4-5
$46/day
Kia Carnival car
Kia Carnival
or similar Van
5
5
4-5
$55/day
Nissan Pathfinder car
Nissan Pathfinder
or similar SUV
5
2
4-5
$68/day
Ford Transit car
Ford Transit
or similar Van
5
3
4-5
$92/day
Cadillac XTS car
Cadillac XTS
or similar Luxury
5
5
4-5
$60/day
Honda Pilot car
Honda Pilot
or similar SUV
5
5
4-5
$73/day
Nissan Rogue car
Nissan Rogue
or similar SUV
5
3
4-5
$45/day
Class Special Car car
Class Special Car
or similar Category
5
5
2/4
$46/day
Hyundai Santa Fe car
Hyundai Santa Fe
or similar SUV
5
3
4-5
$52/day
Best rates found by KAYAK users in the past 48 hours.
Booking Insights

Good to know

Most popular agency

Most popular car type

Average price

Good deal

Hertz
Medium
$64/day
$49/day

KAYAK’s insights & trends for Cheshire car rentals

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

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

You should book your rental car in Cheshire around 18 days before your trip in order to get a below-average price.

What is the best rental car company in Cheshire?

Based on ratings and reviews from real users on KAYAK, the best car rental companies in Cheshire are Dollar (6.4), Global Rent A Car (5.0), and U-Save (4.5).
Dollar
Dollar
Rated 6.4/10
Global Rent A Car
Global Rent A Car
Rated 5.0/10
U-Save
U-Save
Rated 4.5/10
Enterprise Rent-A-Car
Enterprise Rent-A-Car
Rated 0.0/10

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

The cheapest month to rent a car in Cheshire is January at an average cost of $42/day. December is the most expensive month to rent a car in Cheshire when prices are $106/day on average, which tends to be 55% above the yearly average rental price for Cheshire.

What rental car company in Cheshire has the most locations?

Enterprise Rent-A-Car operates 4 locations in Cheshire, more than any other rental company.

KAYAK’s top tips for renting a car in Cheshire

  • 25% of our users found rental cars in Cheshire for $49 or less

FAQs about renting a car in Cheshire

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

    On average a rental car in Cheshire costs $64 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 Cheshire found in the last 2 weeks is $52.

  • Which car rental companies will pick you up at Tweed-New Haven airport (HVN)?

    The only car rental company that offers shuttle or pick-up services from Tweed-New Haven airport to off-airport locations is Rent-A-Wreck.

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

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

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

    A Medium car rental in Cheshire costs $81 per day, on average.

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

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

  • How many car agencies are operating in Cheshire?

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

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

    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 Cheshire?

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

Cheshire 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.

Dollar

6.4

Okay

One location in Cheshire

Show locations

Locations in Cheshire

1211a S. Broad Street

+1 203 265 0324

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

Global Rent A Car

5.0

Fair

One location in Cheshire

Show locations

Locations in Cheshire

380 South Broad Street

Opening times not available

Filters

No reviews available

U-Save

4.5

Mediocre

One location in Cheshire

Show locations

Locations in Cheshire

380 South Broad Street

Opening times not available

Filters

No reviews available

Enterprise Rent-A-Car

No score available yet

4 locations in Cheshire

Show locations

Locations in Cheshire

209 Maple Ave

+1 203 272 0525

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

2500 E Main St

+1 203 755 3770

Monday08:00 - 17:00
Tuesday08:00 - 17:00
Wednesday08:00 - 17:00
Thursday08:00 - 17:00
Friday08:00 - 17:00
Saturday09:00 - 12:00
Sunday00:00 - 00:00

600 North Colony Road

+1 203 634 1233

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

856 N Colony Rd

+1 203 634 1233

Monday07:30 - 17:00
Tuesday07:30 - 17:00
Wednesday07:30 - 17:00
Thursday07:30 - 17:00
Friday07:30 - 17:00
Saturday09:00 - 12:00
Sunday00:00 - 00:00

Filters

No reviews available

Arow Enterprises Corp.

No score available yet

One location in Cheshire

Show locations

Locations in Cheshire

209 Maple Ave, Cheshire

+1 203 272 0525

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

Hertz

No score available yet

One location in Cheshire

Show locations

Locations in Cheshire

1211a S. Broad Street

+1 203 265 0324

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

8.0 Very good

Anonymous, May 2021

KAYAK

Pros:

The staff was very helpful and reassuring. He showed me the exactly where and how to return the key.

Cons:

The light on the oil/engine were both on when I got the car. Thankfully, it was probably just a sensor!

1 out of 1

Thrifty

No score available yet

One location in Cheshire

Locations in Cheshire

1211a S. Broad Street

+1 203 265 0324

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

Anonymous, Jul 2025

Pickup truck

KAYAK
I reserved a pickup truck. Called ahead to confirm that they would have a ram or tundra, they confirmed verbally. I was sent a confirmation email to say the truck would be waiting. Get to a Thrifty or *shifty*, and no trucks! I could maybe wait for someone to bring something from another location and delay my trip, but I had time sensitive engagement, (legal documents to sign) so I couldn’t wait for whoever to come whenever they might have time. Part of this is my own fault because in the time crunch I didn’t have any options, and it’s such a small operation that the only other vehicle with similar capacity on the lot was a mini van, so I was offered the van with the caveat that it was just returned and I would have to clean it out myself. I know this sounds silly but it was my only option. Whoever the previous renters were we’re very abusive to this van, it was filled with sand and vape pens and trash, and on the exterior there were literally parts hanging off the undercarriage that had to be cut and yanked off by the *shifty/hurts agent so they weren’t just scraping along the road. Took the 360 video walk around and thank goodness 😅 because it caught the cracked windshield, so I’m assuming that’s not what the extra $318 dollars 💸 charge was for, although I wouldn’t know because I’ve not received any bill like I asked for, I just saw the rental fee and the extra $318. I got to Bar Harbor Maine and went to put some air in the tires before I noticed a fairly deep gash in the sidewall of the rear passenger side. This was a *probably going to pop and leave me stranded somewhere type gash. After reviewing the 360* walk around video you can see it was there when I took possession of the vehicle. Along with the cracked windshield, and the pieces that had to be cut and yanked off hanging from the undercarriage of the dirty filthy vehicle, which due to time constraints I had to take instead of what I reserved, and had verbal and written communication that would be available and waiting. Which brings me to the point of wondering 🤔 if I should just go ahead and pursue small claims court to recoup my $318 random extra fee that was charged over my rental fee. Don’t rent from *Shifty/Hurtz Meriden.

Car rental locations in or near Cheshire

Traveling to a place near Cheshire?

Rent a car at Cheshire if you plan to visit one of these locations
Essex
Chester

Cheshire car rental information

Pick-up locationCheshire
Car typesSmall, SUV, Medium, Large, Van, Luxury
Rental locations2
Airport locations0
Popular agenciesEnterprise Rent-A-Car, Turo