$49 Car Rental Winchester, MA

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Top Car Deals in Winchester

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

Sat, Dec 6 to Sun, Dec 7

Compact

Ford Focus or similar
  • 5 people
  • Unlimited mileage
Boston, Massachusetts, USA
Ford Focus

$49

includes taxes & fees
$20 per day
found 18 hours ago
Compact Ford Focus
Sat, Dec 6 to Sun, Dec 7

Economy

Chevrolet Spark or similar
  • 4 people
  • Unlimited mileage
Boston, Massachusetts, USA
Chevrolet Spark

$49

includes taxes & fees
$20 per day
found 18 hours ago
Economy Chevrolet Spark
Sat, Dec 6 to Sun, Dec 7

Special

Managers Special or similar
  • 4 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Managers Special

$51

includes taxes & fees
$21 per day
found 18 hours ago
Special Managers Special
Thu, Dec 4 to Fri, Dec 5

Midsize

Mazda 3 4-door or similar
  • 5 people
  • Unlimited mileage
Boston, Massachusetts, USA
Mazda 3 4-door

$52

includes taxes & fees
$22 per day
found 19 hours ago
Midsize Mazda 3 4-door
Sat, Dec 6 to Sun, Dec 7

Standard

Chevrolet Cruze or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Chevrolet Cruze

$53

includes taxes & fees
$23 per day
found 18 hours ago
Standard Chevrolet Cruze
Thu, Dec 4 to Fri, Dec 5

Fullsize

Chevrolet Malibu or similar
  • 5 people
  • Unlimited mileage
BOSTON LOGAN, USA
Chevrolet Malibu

$54

includes taxes & fees
$24 per day
found 19 hours ago
Fullsize Chevrolet Malibu
Wed, Dec 3 to Thu, Dec 4

Premium Crossover

Dodge Durango or similar
  • 7 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Dodge Durango

$72

includes taxes & fees
$38 per day
found 19 hours ago
Premium Crossover Dodge Durango
Thu, Dec 4 to Fri, Dec 5

Standard Elite Special

Ford Mustang Mach-E or similar
  • 5 people
  • Unlimited mileage
Boston, Massachusetts, USA
Ford Mustang Mach-E

$76

includes taxes & fees
$40 per day
found 19 hours ago
Standard Elite Special Ford Mustang Mach-E
Wed, Dec 3 to Thu, Dec 4

Mini Van

CHRYSLER PACIFICA or similar
  • 7 people
  • Unlimited mileage
Boston, Massachusetts, USA
CHRYSLER PACIFICA

$75

includes taxes & fees
$40 per day
found 19 hours ago
Mini Van CHRYSLER PACIFICA
Fri, Dec 5 to Sat, Dec 6

Premium Elite SUV

Audi Q5 or similar
  • 5 people
  • Unlimited mileage
EAST BOSTON, USA
Audi Q5

$101

includes taxes & fees
$63 per day
found 1 day ago
Premium Elite SUV Audi Q5
Sat, Dec 6 to Sun, Dec 7

Luxury

Audi A4 or BMW 3 Series or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Audi A4 or BMW 3 Series

$103

includes taxes & fees
$64 per day
found 18 hours ago
Luxury Audi A4 or BMW 3 Series
Fri, Dec 5 to Sat, Dec 6

Oversize SUV

Lincoln Navigator L Jeep Grand Wagoneer L or similar
  • 7 people
  • Unlimited mileage
EAST BOSTON, USA
Lincoln Navigator L Jeep Grand Wagoneer L

$117

includes taxes & fees
$76 per day
found 1 day ago
Oversize SUV Lincoln Navigator L Jeep Grand Wagoneer L
Thu, Dec 4 to Fri, Dec 5

Luxury Elite

Genesis G80E or similar
  • 5 people
  • Unlimited mileage
Boston, Massachusetts, USA
Genesis G80E

$140

includes taxes & fees
$90 per day
found 19 hours ago
Luxury Elite Genesis G80E

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Lowest prices found within the past 18 hours. Prices and availability subject to change. Additional terms may apply.

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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 $49 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?
Canceling 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.
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 45 miles away.
  • Your next pit stop? It has to be Hartford, which is around 95 miles away. Mark Twain House & Museum is one local highlight you really shouldn't miss.
  • Battery Park is about 190 miles from Winchester and is one of the region's most breathtaking nature spots. Go for a wander around and enjoy the fresh air here.

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 license 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 $49 per day. The next best deal on offer was $51. 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-vacation. 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.
What insurance should I choose for my car rental in Winchester?
After perfectly planning your escape, don't scrimp on safety — add collision protection while booking your Winchester car rental with Expedia. There are many benefits to this plan, including up to $35,000 in primary coverage for collision damage, theft and vandalism. Plus, with a zero-dollar deductible and 24/7 emergency assistance, you'll be able to breathe a little easier should you find yourself in a pickle.

Car Rental Information

 
Popular car types
SUV, Full Size, Economy
 
Car suppliers available
 
Our best deal of the day
$49
 
Our second best deal of the day
$51
 
Our third best deal of the day
$52
 
From the airport to your hotel
Airport Transportation
 
From popular domestic and international airports
Airport Car Rentals

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 from $49.

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 2025

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

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