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, HomeAway 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.

Where to stay around Upperville?

Our 2019 property listings offer a large selection of 65 vacation rentals near Upperville. From 25 Houses to 2 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Upperville for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Upperville?

HomeAway offers a large selection of vacation rentals near lovely places in Upperville. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Patsy Cline Historic House: 57 vacation rentals
  • Bluemont Vineyard: 161 vacation rentals
  • Marterella Winery: 86 vacation rentals
  • Jiffy Lube Live: 119 vacation rentals
  • Museum of the Shenandoah Valley: 51 vacation rentals

But there are many other points of interest around Upperville listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Upperville?

Yes, of course. HomeAway has 25 Houses in Upperville. Our other popular types of vacation rentals in Upperville include:

  • Condos/Apartments: 2 rentals available
  • Villas: 3 rentals available
  • Cabins: 24 rentals available

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

Can I find a vacation rental with pool in Upperville?

Yes, you can select your preferred vacation rental with pool among our 13 vacation rentals with pool available in Upperville. Please use our search bar to access the selection of vacation rentals available.