$59 Car Rental Winchester, MA

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Top Car Deals in Winchester

Tue, Jun 11 - Fri, Jun 14

Special

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

$59

per day
found 7 hours ago
Special EV Managers Special
Sun, Jun 9 - Wed, Jun 12

Midsize SUV

KIA NIRO EV or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
KIA NIRO EV

$67

per day
found 4 hours ago
Midsize SUV KIA NIRO EV
Wed, Jun 12 - Sat, Jun 15

Standard Pickup Regular Cab

Toyota Tacoma or similar
  • 4 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Toyota Tacoma

$84

per day
found 2 hours ago
Standard Pickup Regular Cab Toyota Tacoma
Wed, Jun 12 - Sat, Jun 15

Premium Pickup Regular Cab

Ford F150 or similar
  • 4 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Ford F150

$87

per day
found 2 hours ago
Premium Pickup Regular Cab Ford F150
Tue, Jun 11 - Fri, Jun 14

Compact

Nissan Versa or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Nissan Versa

$90

per day
found 5 hours ago
Compact Nissan Versa
Sun, Jun 9 - Wed, Jun 12

Economy

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

$126

per day
found 3 hours ago
Economy Chevrolet Spark
Sun, Jun 9 - Wed, Jun 12

Midsize Elite

Polestar 2 or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Polestar 2

$136

per day
found 6 hours ago
Midsize Elite Polestar 2
Sun, Jun 9 - Wed, Jun 12

Fullsize Elite Special

Audi A5 Sportback or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Audi A5 Sportback

$136

per day
found 5 hours ago
Fullsize Elite Special Audi A5 Sportback
Sun, Jun 9 - Wed, Jun 12

Fullsize

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

$137

per day
found 6 hours ago
Fullsize Chevrolet Malibu
Tue, Jun 11 - Fri, Jun 14

Luxury

Chrysler 300 or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Chrysler 300

$139

per day
found 2 hours ago
Luxury Chrysler 300
Sun, Jun 9 - Wed, Jun 12

Oversize SUV

Lincoln Navigator L , Cadillac Escalade ESV or similar
  • 7 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Lincoln Navigator L , Cadillac Escalade ESV

$139

per day
found 4 hours ago
Oversize SUV Lincoln Navigator L , Cadillac Escalade ESV
Sun, Jun 9 - Wed, Jun 12

Premium Elite Special

BMW 5-Series or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
BMW 5-Series

$140

per day
found 5 hours ago
Premium Elite Special BMW 5-Series
Sun, Jun 9 - Wed, Jun 12

Luxury Elite SUV

BMW X7 or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
BMW X7

$140

per day
found 4 hours ago
Luxury Elite SUV BMW X7
Sat, Jun 8 - Tue, Jun 11

Standard Elite SUV

Audi Q3 or similar
  • 5 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Audi Q3

$153

per day
found 3 hours ago
Standard Elite SUV Audi Q3
Sun, Jun 9 - Wed, Jun 12

Mini Van

Chrysler Pacifica or similar
  • 7 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Chrysler Pacifica

$173

per day
found 6 hours ago
Mini Van Chrysler Pacifica
Tue, Jun 11 - Fri, Jun 14

Mini Elite Van

Chrysler Pacifica or similar
  • 7 people
  • Unlimited mileage
East Boston, Massachusetts, USA
Chrysler Pacifica

$206

per day
found 2 hours ago
Mini Elite Van Chrysler Pacifica

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* Price found within the past 60 days. Click for updated prices.

Frequently asked questions

How much is a rental car per day in Winchester?
Car rentals in Winchester had a low daily rate of just $59 within the past seven days. At prices like this, you’ll be zipping around in a cool ride with cash to spare.
Can I rent a car from Logan Intl. Airport (BOS)?
Logan Intl. Airport (BOS) has lots of options just a quick commute away. Find a ride that suits you from Alamo, National Car Rental, Hertz, Budget or Avis.
What happens if I need to cancel my Winchester car reservation?
We understand that things can change at the last minute. That’s why a large number of prepaid reservations allow for a total refund if you cancel six hours in advance of collecting the car. Your cancellation policy should include all the info you need. If you can’t find the answer there, our Customer Service Portal is here to help.
What types of cars can I rent in Winchester?
Affordability, ease of parking and excellent mileage are just some of the reasons compact cars are the preference in Winchester. Their small size makes them perfect for getting around the city. They’re a good fit for solo travelers, couples and families on a budget. Of course, how you cruise around is your call! Go even smaller with an economy or mini, or get more legroom with an intermediate or a full-size. Need a little luxury? You’ll like our premium options.
Where can I go on a road trip from Winchester?
There are so many things to do in Winchester, but venture farther afield and you’ll find more sightseeing magic. Book a set of wheels and you can roam around the surrounding region at your leisure. Add these fantastic places to your itinerary:

  • New Haven is roughly 120 mi from Winchester. Popular attractions like Yale University deserve to be at the top of your list here.
  • Around 45 mi away, Providence is also popular with wanderers. Make time to take in Brown University while you’re in town. It’s one of the reasons people love this buzzing city.
  • Mount Washington State Park is approximately 130 mi from Winchester and is one of the region’s most spectacular nature spots. Go for a wander around and enjoy the fresh air here.

Why should I rent a Winchester car with Expedia?
You’ll find savings for the savvy traveler on Expedia. Whether you want something that’ll fit the entire crew or just the two of you, browse the deals from the car rental companies in Winchester. Our exclusive offers and discounts will help you score the lowest price possible. Combine your car with your hotel and flights to save even more. Chasing a few things to do in Winchester? Add some activities to your vacation package later on!
How do I find the best car rental deals in Winchester with Expedia?
Pick up an incredible deal with Expedia. All you have to do is choose your wheels, select your dates and pickup and drop-off locations, and browse offers from all the major providers. Make even bigger savings when you combine your Winchester car rental with hotel or flight bookings.
How old do you have to be to rent a car in Winchester?
You need to be at least 21. But there are some age-related rules you should keep in mind before you lock in your wheels in Winchester. If you’re a younger motorist, many rental outlets will charge an additional fee and limit the sorts of vehicles you can rent. The surcharge amount, and which ages it applies to, varies between companies. Take a few moments to compare the requirements.
What do you need to rent a car in Winchester?
Most rental companies will ask for these two things — a current driver’s license and a credit card in your name. If you decide to opt out of the supplier’s insurance plan, proof of your own coverage may also be needed. Check your policy so you know what to bring when it’s time to collect your car.
What is the cheapest car rental in Winchester?
We looked into prices over the last seven days and found that the most affordable daily rate was $59. The next best price to rent a set of wheels in Winchester was $67 a day. 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?
Whether you plan to hang around Winchester or discover what’s beyond, you can book a long-term rental with Expedia. Enter your trip information and pick-up/drop-off locations and we’ll help you find excellent long-term car rental deals.
Where can I find a Winchester car rental if I am younger than 25?
If you’re a younger driver looking for a car rental in Winchester, check the policies of the car rental companies you’re interested in. Some may rent to drivers under 25, some may not. There may be surcharges if you’re between 21 and 24 years old. To escape any surprises on pickup, make sure you know what to expect.
What insurance should I choose for my car rental in Winchester?
A thorough insurance plan is a fantastic idea for your upcoming Winchester escape. That’s why we recommend choosing collision protection while organizing your rental car with Expedia. This covers your vehicle from theft, accident damage and vandalism. Some destinations may require a minimum level of liability insurance. This may already be included in your rental price or your own auto insurance, so check what you’re covered for and whether you need it.

Car Rental Information

 
Popular car types
SUV, Full Size, Economy
 
Car suppliers available
 
Our best deal of the day
$59
 
Our second best deal of the day
$67
 
Our third best deal of the day
$84
 
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 $59.

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 2024

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