Destination guide

Find the perfect holiday rental for your Upperville getaway

Learn about the unique charm of Upperville with a stay in a holiday home rental. One of the city's many top draws is its restaurants. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 holiday 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 centre:

  • 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 centre:

  • 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

Travelling 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 centre. 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 holiday rentals are available around Upperville?

Our 2020 accommodation listings offer a large selection of 60 holiday lettings around Upperville. From 21 cottages to 26 houses, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Upperville? offers a large selection of holiday accommodations near great places in Upperville. From travellers, the most popular points of interest to stay near are:

  • Barns of Rose Hill: 127 holiday lettings
  • Winchester Medical Center: 58 holiday lettings
  • Warren Rifles Confederate Museum: 176 holiday lettings
  • Dinosaur Land: 86 holiday lettings
  • Burwell-Morgan Mill: 115 holiday lettings

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

Can I rent Cottages in Upperville?

Yes, of course. offers 21 Cottages in Upperville. Our other popular types of Upperville holiday rentals include:

  • Houses: 26 self catering accommodations
  • Cabins: 21 self catering accommodations
  • Bungalows: 21 self catering accommodations

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

Can I find a holiday accommodation with pool in Upperville?

Yes, you can select your preferred holiday accommodation with pool among our 10 holiday homes with pool available in Upperville. Please use our search bar to access the selection of holiday rentals available.