Winchester Cheap Car Rentals & Car Hire Deals

Compare rent a car rates in Winchester from popular car rental companies

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Explore Winchester with Cheap Car Rentals and Car Hire Deals

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

Economy

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

Compact

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

Midsize

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

SUV

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

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Frequently asked questions

How much is a rental car per day in Winchester?
Car rentals in Winchester had a low daily rate of just within the past seven days. With prices this good, you'll be zipping around in a cool ride with cash to spare.
Can I rent a car from Logan Intl. Airport (BOS)?
Even though there are no car rental offices in the terminal building at Logan Intl. Airport (BOS), there's a great range of options nearby. Budget, Dollar, Payless, Enterprise and Thrifty all offer some terrific deals on rental vehicles.
What happens if I need to cancel my Winchester car reservation?
Cancelling a reservation six hours before the scheduled pickup time should allow for a full refund. But this is not always guaranteed. It's good to check your itinerary and rental agreement. Still stuck for answers? Jump onto our Customer Service Portal.
What types of cars can I rent in Winchester?
Keep things low-cost with an economy, style it up in a premium ride or choose something in the middle, like a mid-size. But it's hard to go past a compact car — the number one choice in Winchester. They're easy to handle and park, fuel-efficient and a wise idea if you're driving around cities. An upgrade from economy, you can expect a little more room and comfort at a price that won't hurt your budget.
Where can I go on a road trip from Winchester?
Once you've covered all the interesting attractions in Winchester, there's plenty more to discover in the surrounding area. Pick up the keys to a rental car, stow your bags in the trunk and get going. We've pulled together some drives we know you'll enjoy:

  • You'll find Roger Williams Park Zoo and countless other amazing sights in Providence. From Winchester, it's around 72 kilometres away.
  • Your next pit stop? It has to be Hartford, which is around 153 kilometres away. Mark Twain House & Museum is one local highlight you really shouldn't miss.
  • Battery Park is about 306 kilometres from Winchester and is one of the region's most breathtaking nature spots. Go for a wander around and enjoy the fresh air here.

Why should I rent a Winchester car with Expedia?
Expedia is the best place to book your next ride. With suppliers in Winchester to select from, we're passionate about delivering terrific deals. One Key™ members always get our best prices, so sign up to unlock more savings. And, when you bundle bookings into a Winchester holiday package, you'll score even bigger bargains. Car rentals, hotels and flights — Expedia has everything you need in one place.
How do I find the best car rental deals in Winchester with Expedia?
Check out customer reviews, choose your preferred car class and compare offers from top suppliers. Expedia makes it a cinch to get the best deal on your rental wheels. Combine your Winchester car rental with hotel or flight bookings and start your road trip with even more savings.
How old do you have to be to rent a car in Winchester?
In most cases, the requirement is 21 years and over in Winchester. Be aware that most companies will charge a young renter fee. Read the fine print before you book your ride, as rules may differ between rental car providers. Bear in mind that if you're planning to rent a specialty vehicle or a large car like an SUV, rules may require drivers to be older than 21.
What do you need to rent a car in Winchester?
Renting a car in Winchester is simple. Normally, all you'll need is a valid driver's licence and a credit card in your name. After selecting the perfect set of wheels, look up the terms and conditions to ensure there are no further requirements before pickup.
What is the cheapest car rental in Winchester?
The lowest car rental price in Winchester within the past seven days was per day. The next best deal on offer was . 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?
Yes, so there's no need to rebook a rental vehicle mid-holiday. Visit our long-term car rental deals page, enter your details and book a ride to call your own for however long you need.
Where can I find a Winchester car rental if I am younger than 25?
If you're a younger driver hoping to rent a car in Winchester, check the terms and conditions of the rental companies you're interested in. Some may rent to drivers under 25  some may not. There may be additional costs if you're between 21 and 24 years old. To escape any surprise fees and charges at the rental desk, make sure you know exactly what to expect.

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