Discover a selection of 61 vacation rentals in Upperville, VA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $192 per night, and cottages and houses are popular options for a stay in Upperville. Either way, you'll find a rental for everyone's needs.
Destination guide

Find the perfect vacation rental for your Upperville getaway

Experience the unique character of Upperville with a stay in a vacation home rental. One of the city's many top draws is its restaurants. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.


Activities and attractions in and around Upperville

Are you searching for top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Upperville has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Paris Barns (3.4 mi / 5.4 km)
  • Bluemont Vineyard (7.9 mi / 12.8 km)
  • Veramar Vineyard (8.8 mi / 14.2 km)
  • Appalachian Trailhead (10.3 mi / 16.6 km)
  • Chrysalis Vineyards (11.8 mi / 19 km)
  • Dinosaur Land (14.2 mi / 22.9 km)
Natural features

Exploring the natural features in Upperville

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Upperville is a great place to spend some time outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • State Arboretum of Virginia (10.6 mi / 17 km)
  • Front Royal Entrance Shenandoah National Park (17.6 mi / 28.4 km)
How to get there

Traveling to and around Upperville

The nearest airport is in Washington, DC (IAD-Washington Dulles Intl.), located 23.9 mi (38.4 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away.

How many vacation rentals are available around Upperville, VA?

Our 2021 property listings offer a large selection of 61 vacation rentals around Upperville. From 14 cottage rentals to 49 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Cottages in Upperville?

Yes, of course. Vrbo has 14 Cottages in Upperville. Our other popular types of vacation rentals in Upperville include:

  • Houses: 49 rentals available
  • Cabins: 14 rentals available
  • Bungalows: 14 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bed & breakfasts and more.

Can I find a vacation rental with pool in Upperville?

Yes, you can select your preferred vacation rental with pool among our 8 vacation rentals with pool available in Upperville. Please use our search bar to access the selection of vacation rentals available.