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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, New Hampshire, USA
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Winchester, New Hampshire, USA
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Winchester, New Hampshire, USA
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Winchester, New Hampshire, USA
Jeep Compass
SUV Jeep Compass

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Frequently asked questions

How much is a rental car per day in Winchester?
Within the past seven days in Winchester, you could have taken off in a rental car for as little as per day.
Can I rent a car from Keene, NH (EEN-Dillant-Hopkins)?
Enterprise is a short commute from the terminal and the only car rental option. Reserve your ride today to avoid missing out.
What happens if I need to cancel my Winchester car reservation?
If you have to switch up your plans, most prepaid bookings are eligible for a full refund. Cancellations will need to be made a minimum of six hours ahead of the collection time. Check your rental policy for any exclusions. Your itinerary will have more details, or you can visit our Customer Service Portal for more information.
Where can I go on a road trip from Winchester?
There's heaps to do in Winchester, but head farther afield and you'll find more sightseeing magic. Book a set of wheels and you can discover the surrounding region at your own pace. Add these awesome drives to your list:

  • Providence is about 80 miles from Winchester. Notable tourist attractions like Roger Williams Park Zoo deserve a place on your must-see list here.
  • Why not see everything on offer in Hartford too? Popular tourist attractions in this happening city include Mark Twain House & Museum. Hartford is about 70 miles from Winchester.
  • Get into the great outdoors and inhale the fresh air at Battery Park. It's about 170 miles from Winchester.

How do I find the best car rental deals in Winchester with Expedia?
Finding an amazing deal on your Winchester rental car is a cinch with Expedia. Choose your preferred car type, add in a few more details and compare prices from leading suppliers. Why not add flights and hotels to your booking? You'll unlock even bigger savings when you create a vacation package.
How old do you have to be to rent a car in Winchester?
You'll need to be at least 21 to pick up the keys to a rental vehicle in Winchester. Take note that young drivers may only be able to rent from a few car classes, such as economy and compact. Higher age limits generally apply for larger vehicles like premium SUVs. Many providers will also charge a young renter fee. Read through the rules before clicking book and factor any surcharge into your travel budget.
What do you need to rent a car in Winchester?
Be prepared to present a valid driver's license and a credit card at the rental counter. Before pickup, check with your selected rental company whether anything else is needed. For example, you may also need to show proof of insurance.
What is the cheapest car rental in Winchester?
Based on prices within the past seven days, you could've hopped into the driver's seat of your own rental car for just a day. The second lowest daily rate in Winchester 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?
Whether you plan to stay in Winchester or discover what's beyond, it's easy to reserve a long-term rental with Expedia. Enter your trip dates and pick-up/drop-off locations and we'll help you find affordable long-term car rental deals.
Where can I find a Winchester car rental if I am younger than 25?
You'll need to look into the age policy of the Winchester rental suppliers you're considering. If you're under 25 years of age, some will charge additional fees. It's better to know this before collecting the vehicle so you can budget accordingly. Every rental car company has its own policies for younger drivers, so it'd be wise to do your research.
What insurance should I choose for my car rental in Winchester?
It's a good idea to have collision damage protection to safeguard your Winchester rental car against theft, accident damage and vandalism. And with Expedia, it's easy to purchase this insurance for your vehicle during the booking process. Covering primary physical damage of up to $35,000, it also offers round-the-clock emergency assistance and no deductible should you need to make a claim. Change of plans? If you cancel your insurance before your scheduled pick-up time, you'll get all your money back.

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 2025

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

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