Choose from 4 vacation rentals located in Upperville, Virginia. Top filters in Upperville include Air conditioner, Laundry, and Internet / Wifi. Prices range from $208 to $844 per night. Our most popular vacation rental types near Upperville are Apartment and Hotel.

Top vacation rentals in Upperville

5 bedrooms, iron/ironing board, bed sheets
5.0
Outstanding(15 Reviews)
Historic house in Upperville! Wineries, equestrian events, great location!
House
 in Upperville
11 guests · 5 bedrooms · 3 baths
Air conditioner · Laundry

House in Upperville, for $844 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Outdoor dining
5.0
Outstanding(2 Reviews)
Historic spacious home in the heart of Upperville, VA
House
 in Upperville
10 guests · 4 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette

Nestled in Upperville, this House is perfect for your next vacation. Enjoy Historic spacious home in the heart of Upperville, VA 's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Private kitchen
4.8
Outstanding(10 Reviews)
Hunt Country cottage in Upperville!
Cottage
 in Upperville
3 guests · 2 bedrooms · 1 bath
Air conditioner · Internet / Wifi · Laundry

Looking for the perfect place to call home during your trip to Upperville? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Smart TV
5.0
Outstanding(4 Reviews)
Cozy Country Getaway in the Heart of Upperville
House
 in Upperville
5 guests · 2 bedrooms · 2 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner

This House for $294 in Upperville, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Upperville

Upperville travel guide

Let us help you plan your perfect Upperville vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Upperville, and more.

Frequently asked questions

What do I need to know before visiting Upperville, VA?

Before visiting Upperville, VA, you should know the following:

  • Upperville is located in Fauquier County, VA.
  • The town is home to the Upperville Colt & Horse Show, the oldest horse show in the United States.
  • The town is known for its historic sites, including the Upperville Historic District, Belle Grove Plantation, and the Upperville-Amissville Rural Historic District.

The area is also home to a variety of outdoor activities, including hiking, biking, and horseback riding. In addition, Upperville is located close to several wineries and breweries, making it a great destination for a day trip or weekend getaway.

What are the must-visit tourist attractions in Upperville, VA?

Upperville, VA is a great place for tourists to explore. Here are some must-visit attractions in the area:

  • Upperville Colt & Horse Show
  • Upperville Historic District
  • Red Fox Inn & Tavern
  • Luray Caverns

The Upperville Colt & Horse Show is the oldest horse show in the country, and it's a great way to experience the area's rich equestrian history. The Upperville Historic District is a great place to explore the area's history and architecture. The Red Fox Inn & Tavern is a great way to experience the area's hospitality and culture. Finally, the Luray Caverns are a must-visit attraction to explore the area's unique geological features.

How can I get around in Upperville, VA?

You can get around Upperville, VA by:

  • Driving
  • Riding a bike
  • Using public transportation

Where can I find affordable accommodation in Upperville, VA?

Upperville, VA is a great place to stay for an affordable vacation. Here are some great options for accommodation:

  • Upperville Inn: Offering modern rooms with free Wi-Fi and flat-screen TVs at an affordable price.
  • Upperville Motel: A budget-friendly option, with rooms featuring air conditioning and a microwave.
  • Upperville Suites: This hotel offers spacious suites with fully-equipped kitchens and free Wi-Fi.
  • Upperville Bed & Breakfast: Enjoy a cozy stay in a historic home with free breakfast.

What is the culture like in Upperville, VA?

Upperville, VA is a small town located in Fauquier County. It is an area rich in history, with a culture that reflects the rural, agricultural roots of the area. Here are five aspects of the culture in Upperville, VA:

  • Family values: Upperville is a tight knit community, and families are highly valued.
  • Sense of history: Upperville has a rich history, and many of its buildings and landmarks are steeped in local lore.
  • Outdoor activities: Upperville is home to several parks and trails, making it a great spot for outdoor recreation.
  • Agriculture: Upperville is home to several farms and orchards, and is known for its abundance of fresh, locally grown produce.
  • Small town charm: Upperville is a quaint and charming town, with a friendly atmosphere and a close-knit community.

Is Upperville, VA safe to travel to?

Upperville, VA is generally considered to be a safe place to travel to. Here are a few factors that contribute to its safety:

  • Low crime rate
  • Friendly locals
  • Well-maintained infrastructure
Overall, Upperville, VA is a great place to visit and explore.

What are the popular shopping destinations in Upperville, VA?

Popular shopping destinations in Upperville, VA include:

  • Upperville Country Store
  • Upperville Antiques & Design
  • Upperville Farmers Market

Visitors can find everything from local produce to antiques and collectibles in Upperville's shopping destinations.

What are the best neighborhoods to visit in Upperville, VA?

Upperville, VA is home to many wonderful neighborhoods to visit. Here are the best neighborhoods to explore:

  • Downtown Upperville: Offers a variety of shops, restaurants, and entertainment.
  • The Countryside: A rural area with stunning views of the countryside.
  • The Waterfront: A scenic area with many outdoor activities.

Where is Upperville, VA?

Upperville, VA is located in Fauquier County, Virginia, about an hour west of Washington D.C. It is a small, rural town with a population of only about 280 people. Upperville is known for its horse farms, and is home to the Upperville Colt and Horse Show which is the oldest horse show in the United States.

What are the most popular vacation rental amenities in Upperville, VA?

Upperville, VA is a great place to find vacation rentals that offer a variety of amenities to make your stay more enjoyable. Some of the most popular amenities in Upperville, VA include:

  • Fully equipped kitchens
  • High-speed internet
  • Air conditioning
  • Private outdoor spaces
  • On-site laundry facilities

These amenities make it easier to cook meals, stay connected, and relax while on vacation. Additionally, many of the rentals offer outdoor activities like swimming pools, tennis courts, and hiking trails to help you make the most of your time in Upperville, VA.

What are the top things to do in Upperville, VA?

Upperville, VA is a great place to visit, and there are plenty of activities to enjoy. Here are the top things to do in the area:

  • Visit Sky Meadow State Park
  • Visit Ashby's Gap Region
  • Take a tour of Belle Grove Plantation
  • Explore the historic town center

From exploring the scenic parks and historic sites, to discovering hidden gems in the town center, Upperville, VA has something for everyone!

What is the price range for rentals in Upperville?

Vacation rentals in Upperville have a price range between $208-$844. The average price for rentals in Upperville is $504 per night.

What are the most popular vacation rental amenities in Upperville?

  • Air conditioner
  • Laundry
  • Internet / Wifi

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