$74 Car Rental Upperville, VA

Reasons to book a car rental in and around Upperville

Renting a car in Upperville provides the freedom and flexibility to explore the area at your own pace. With a rental car, you can easily visit attractions such as Sky Meadows State Park, located just 4 miles away, ideal for outdoor and adventure experiences. If you're interested in local culture, the historic Myron Glaser Cabin Tract is only 5 miles from Upperville, while the Middleburg Historic District, a charming historic area, is 8 miles away.

A rental car is especially convenient for families or those traveling with luggage, making it easier to manage your belongings while you explore. You can venture to nearby cities like Middleburg, which is 8 miles away, featuring art galleries and parks, or Paris, located just 4 miles away, where you can enjoy both the Shenandoah River and Sky Meadows State Park. Delaplane, 6 miles from Upperville, also offers scenic views and attractions. The ability to travel flexibly allows you to make the most of your trip while discovering the beautiful surroundings of Upperville.

Where to stay around Upperville

• Middleburg: Located 8 miles from Upperville, Middleburg is a charming city known for its outdoor adventures and beautiful scenery. It offers various activities, including visits to the Middleburg Historic District and Red Fox Fine Art gallery. The area is surrounded by natural attractions like national state parks and lakes, making it perfect for nature enthusiasts. Food and drink options abound, particularly for those interested in local wineries and vineyards.
• Purcellville: Situated 14 miles from Upperville, Purcellville is an excellent destination for outdoor lovers. This city features numerous recreational areas and is close to Patrick Henry College and the Blue Ridge Center for Environmental Stewardship. Visitors can enjoy the scenic W&OD Trail, perfect for outdoor activities. Additionally, Purcellville offers a variety of dining options, including local wineries and vineyards, enhancing the experience for travelers seeking tasty refreshments.
• Bluemont: Just 9 miles from Upperville, Bluemont is known for its romantic atmosphere and outdoor experiences. Travelers can explore the Rolling Ridge Conservancy and Great Country Farms, along with enjoying the scenic landscapes at Bears Den Park. The area is ideal for eco-friendly adventures and offers access to nearby wineries and breweries for those looking to unwind with local beverages.

10 tips to save on your car rental in and around Upperville

Finding the cheapest car rentals in Upperville

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If the deals that are available on our page do not suit your needs, then enter Upperville into the search wizard at the top of the page. We will compare all the best deals available for your car rental in Upperville and provide you with a list of the cheapest options, with no added fees.

Renting a car in Upperville

Pay at pickup is available, so you don’t have to worry about spending your money until you arrive at your vehicle in Upperville. 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 Upperville

Prices are subject to seasonal change depending on when you decide to arrange your car rental but right now you can book from $74.

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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