Car Rental Winchester, CT

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Top Car Deals in Winchester

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

Economy

Chevrolet Spark or similar
  • 4 people
Winchester, Connecticut, USA
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Winchester, Connecticut, USA
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Winchester, Connecticut, USA
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Winchester, Connecticut, USA
Jeep Compass
SUV Jeep Compass

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Frequently asked questions

How much is a rental car per day in Winchester?
The daily price of rental cars in Winchester within the past seven days was as low as . With your own affordable set of wheels, the sights in and around this place are well within your reach.
What happens if I need to cancel my Winchester car reservation?
Our Customer Service Portal has all the details about cancellations. In nearly all cases, full refunds are available if a booking is canceled more than six hours prior to pickup. Be sure to read the rental agreement to double-check if there are any exemptions.
Where can I go on a road trip from Winchester?
Winchester has plenty to keep you busy, but don't restrict yourself to one place. Rent some wheels and take to the road to discover what else awaits in the wider region. Here are some places to consider:

  • Providence is around 90 miles from Winchester. Well-known tourist spots like Roger Williams Park Zoo should be high on your list while you're in town.
  • Why not see all that's on offer in Albany too? Notable sights here include The Egg. Albany is approximately 60 miles from Winchester.
  • Get into the great outdoors and take in the serenity at Plymouth Rock. It's approximately 130 miles from Winchester.

How do I find the best car rental deals in Winchester with Expedia?
Browse our huge range of rental cars, check out customer ratings and compare prices from top suppliers. In just a few clicks, Expedia will help you find the best deal on your ride. Got a hotel or flight booking? Add on your Winchester car rental and save even more.
How old do you have to be to rent a car in Winchester?
In Winchester, the requirement is usually 21 and over. Most companies will charge additional fees for young drivers, which can vary depending on the rental location. Rental policies for young drivers may restrict certain vehicles, such as specialty cars, and require comprehensive insurance to be taken out. It's a good idea to check the fine print before booking your wheels.
What do you need to rent a car in Winchester?
Two things — your driver's license and a credit card in your name. Most car rental companies will offer you insurance, which is optional. But you may have to provide proof of alternative coverage if you choose to opt out. Be sure to check with your rental provider to avoid any problems.
What is the cheapest car rental in Winchester?
and were the two lowest daily prices for rental cars in Winchester within the past seven days. 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?
You can, and the great news is companies often offer lower prices the longer you rent. Look up our long-term car rental deals in Winchester and drive off with an amazing bargain.
Where can I find a Winchester car rental if I am younger than 25?
Whether or not you can rent a vehicle if you are under 25 years old in Winchester often depends on the rental supplier you choose. Some outlets have a surcharge for young drivers between 21 and 24 years old, yet other companies may not have any extra fees for this age range. Be sure to go through the terms and conditions of your prospective rental company to escape extra costs when picking up your keys.
What insurance should I choose for my car rental in Winchester?
After carefuly planning your road trip, don't skimp on your insurance — choose collision protection while reserving your Winchester rental vehicle with Expedia. There are numerous benefits to this plan, including up to $35,000 in primary coverage for accident damage, theft and vandalism. Plus, with a zero-dollar deductible and 24/7 emergency assistance, you can breathe a little easier if a mishap occurs.

Car Rental Information

 
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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 .

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 2026

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

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