Upperville, Virginia holiday accommodation: short-term house rentals & properties

Scroll through and select from holiday rentals in Upperville to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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Find the best place to stay - Upperville

The Mill House in Upperville -

Sleeps 8 · 4 bedrooms · 2+ bathrooms

Historic house in Upperville! Wineries, equestrian events, great location!

Sleeps 11 · 5 bedrooms · 3 bathrooms

Peace of mind
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More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

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

Do you want to discover things to do in the city? Venture out of your cosy holiday rental and check out everything that Upperville has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

Delaplane Cellars (4 mi / 6.4 km)
Barrel Oak Winery (7.5 mi / 12 km)
Bluemont Vineyard (7.7 mi / 12.4 km)
Tudor Day Spa (8.2 mi / 13.2 km)
Greenhill Winery & Vineyards (9.9 mi / 16 km)
Chrysalis Vineyards (11.6 mi / 18.7 km)

Exploring the natural landscape of Upperville

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Upperville. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

Sky Meadows State Park (3.8 mi / 6.2 km)
Glenwood Park (7.1 mi / 11.4 km)
State Arboretum of Virginia (10.5 mi / 16.9 km)
Shenandoah Lake Beach (15.5 mi / 24.9 km)
Mackintosh Fruit Farm (16.2 mi / 26.1 km)
Shenandoah River (16.6 mi / 26.7 km)

Transport options to and around Upperville

The nearest airport is in Washington Dulles International Airport (IAD), located 23.7 mi (38.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Upperville?

Houses are the most popular type of holiday home in Upperville, according to our data. Even if you've got something else in mind, Stayz has holiday homes in many shapes and sizes. Look through our options to find your ideal fit.

How much does it cost to rent a holiday home in Upperville?

Property type, length of stay and time of year are among the factors that can affect the price of a holiday home. Simply enter your dates of travel to find your perfect escape. From cosy chalets to plush villas, all Stayz holiday homes offer amazing value.

How much does it cost to rent a beach house in Upperville?

Prices for beach houses in Upperville vary depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Stayz and the number of guests to see your options and prices. From there you can use our filter tool to refine your search by ratings, nearby activities, amenities and more.

What are popular home amenities in Upperville?

Some of the most popular home amenities people look for in Upperville are a firepit, a barbecue grill and a swimming pool. Whether you're hitting the road with your besties, family or even pets, Stayz holiday homes provide the best amenities for making epic memories with the people you love.

How old do you have to be to rent a holiday home in Upperville?

The minimum age allowed can vary across properties on Stayz, so be sure to look at the rules of the holiday home in Upperville you want to book. But normally, it's 16, 18 or 21.

How long can I rent a holiday home in Upperville for?

The amount of time you can stay in an Upperville holiday home for is down to each property. Just enter your travel dates to view options offering longer term stays. They include all the things you need to make your extended holiday more convenient and comfortable, like laundries and air conditioning. Some Stayz holiday homes may also offer weekly or monthly discounts, so you can stay even longer for less.