Upperville vacation rentals

We found 216 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Upperville that are perfect for your trip. Vacation homes offer the best amenities for your family, friends, or furry companion, such as WiFi and a pool. At the end of the day, you'll be sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Upperville

Showing deals for:Jun 12 - Jun 19

Image gallery for Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Bay window view from living room
10 out of 10, Exceptional, (76 reviews)
Exceptional
(76 reviews)

Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

Linden

9% off
Price is $483
$3,380 for 7 nights
All fees included
Virginia Wine Country Retreat 60 mi. from DC<br><br><br>

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Find out more about Upperville

Why visit Upperville

  1. Outdoor Adventures: Enjoy a variety of outdoor activities in the scenic countryside surrounding Upperville.
  2. Historic Sites: Explore notable historic homes and sites that showcase the rich heritage of the area.
  3. Charming Downtown: Stroll through the quaint downtown of Warrenton, filled with friendly faces and local shops.
  4. Diverse Accommodations: Choose from a range of vacation rentals, from cozy homes to luxurious properties.
  5. Family-Friendly Activities: Find engaging experiences perfect for families, ensuring fun for all ages.

Popular types of accommodation in Upperville

If you're planning a getaway to Upperville, selecting the perfect accommodation is key. From charming houses and cozy cabins to comfortable apartments, Upperville offers a variety of options to suit your needs. Whether you're searching for homes in Upperville or a house in Upperville, you'll find the ideal spot to relax and unwind. Explore your options and enjoy a memorable stay in this picturesque destination!

  • Houses: The top choice for visitors to Upperville, offering spacious accommodations perfect for families or friends.
  • Apartments: A favored option for those seeking convenience and modern amenities in a home-like setting.
  • Cabins: Ideal for nature enthusiasts, these rentals provide a rustic escape surrounded by beautiful landscapes.
  • Cottages: A charming and cozy option, perfect for a romantic getaway or a peaceful retreat.
  • Chalets: A unique lodging choice that combines comfort with a touch of mountain charm.**

Top attractions in Upperville

Upperville, Virginia, is a charming destination perfect for outdoor adventures and scenic exploration. Visitors can enjoy a variety of attractions, including historic homes, urban parks, and notable historic sites. Whether you're looking for family-friendly activities, cultural experiences, or simply want to tour local homes and enjoy virtual tours, Upperville offers something for everyone. Don't miss the opportunity for house hunting in this picturesque area!

  1. Sky Meadows State Park: Experience the great outdoors with hiking trails, stunning views, and vibrant scenery. Perfect for adventure seekers and nature lovers alike, this park offers a serene escape just 4 miles from Upperville.
  2. Paris Barns: Discover the charming scenery at Paris Barns, a picturesque attraction located 4 miles away. Enjoy the tranquil atmosphere and beautiful landscapes, ideal for relaxation and photography.
  3. Front Royal Entrance Shenandoah National Park: A gateway to outdoor adventures, this visitor center is 18 miles from Upperville. Explore family-friendly activities, breathtaking nature, and diverse trails in the iconic Shenandoah National Park.

Things to do recommended for couples

For a romantic getaway in Upperville, explore Bluemont Vineyard for wine and stunning views, enjoy a show at Tally Ho Theatre, or savor the outdoor ambiance at Marterella Winery. Each venue offers a unique blend of romance and entertainment, perfect for couples looking to create lasting memories.

Things to do recommended for families

Families can have a blast at Fireman's Field for sports, skate at Haymarket IcePlex for some icy fun, or unwind at Jim Barnett Park, perfect for relaxation and wellness. Each spot offers unique experiences just a short drive from Upperville!

Things to do recommended for groups

Experience adventure at Watermelon Park Campground, perfect for families and outdoor fun, just 8 miles away. For adrenaline seekers, visit Summit Point Motorsports Park, located 17 miles from Upperville. Don’t miss the scenic Tuckers Lane Trailhead, an 11-mile trek offering stunning views and outdoor excitement.

What do I need to keep in mind when booking a vacation in Upperville

When traveling with a group, family, pets, or planning an extended stay, it’s important to use the right filters to match your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Upperville with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Upperville with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Upperville: For many, a family vacation isn’t truly complete without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Upperville: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Upperville

Upperville, Virginia, offers a delightful escape for outdoor enthusiasts and families alike. Explore the charming downtown of Warrenton, steeped in history and lined with friendly faces, perfect for leisurely strolls. Venture into the surrounding countryside for breathtaking scenery and adventurous activities. With its inviting atmosphere and rich heritage, Upperville provides a unique blend of relaxation and exploration for every traveler.

  • Ashburn: Located 22 miles from Upperville, Ashburn offers a vibrant mix of family-friendly activities and business opportunities. This growing city features several shopping malls and recreational areas, making it a perfect destination for those looking to spend a day shopping or enjoying outdoor fun. Highlighted local attractions include serene parks and picturesque lakes, providing a peaceful escape from the hustle and bustle. Whether you're winding down at a local beach or enjoying a picnic in the park, Ashburn is a great stop for leisure and relaxation.
  • Middleburg: Just 8 miles from Upperville, Middleburg is renowned for its stunning outdoor scenery and adventurous spirit. This charming town is a gateway to incredible recreational activities, from hiking in the nearby national parks to exploring the scenic countryside. Middleburg's quaint shopping centers offer unique boutiques and local artisan goods, making it a delightful place to spend an afternoon. Don't miss the chance to visit the breathtaking lakes and state parks that surround the area, perfect for nature lovers and adventure seekers alike.
  • Winchester: Located 20 miles from Upperville, Winchester boasts a rich historical background alongside its outdoor adventure opportunities. The city is a hub for recreation, with numerous parks and educational attractions that provide a fun and informative experience for visitors. Shopping enthusiasts will appreciate the variety of shopping mall centers available. Nearby, you'll find stunning national parks and serene lakes, ideal for hiking, picnicking, or simply enjoying the natural beauty of the region. Winchester is a must-visit for those seeking both adventure and history.

Best time to go to Upperville

If you're planning a trip to Upperville, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from April to June, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.8°F (-0.1°C)Light RainMostly SunnyModerately LowSlightly Low
February35.2°F (1.8°C)Light RainMostly SunnyAverageAverage
March42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
April53.4°F (11.9°C)Light RainMostly SunnyModerately HighAverage
May62.8°F (17.1°C)Light RainMostly SunnyModerately HighAverage
June71.2°F (21.8°C)Light RainMostly SunnyModerately HighAverage
July76.5°F (24.7°C)Light RainMostly SunnyAverageAverage
August74.3°F (23.5°C)Light RainMostly SunnyAverageSlightly High
September67.5°F (19.7°C)Light RainMostly SunnyAverageSlightly High
October56.3°F (13.5°C)Light RainMostly SunnyModerately LowSlightly High
November44.1°F (6.7°C)Light RainMostly SunnyAverageAverage
December37.2°F (2.9°C)Light RainMostly SunnyModerately LowSlightly Low

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking an extended stay can lead to considerable savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. It's definitely rewarding to be the planner! Become a member of our One Key rewards program to enjoy exclusive savings and start earning OneKeyCash™ on eligible stays. Sign up today and begin reaping the benefits!

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a dedicated area to plan new trips, pick up right where you left off, or manage your travel plans efficiently. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Find the perfect vacation rental for your Upperville getaway

Learn about the unique charm of Upperville with a stay in a private vacation home. 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 things to do in the city? Venture out of your cozy vacation rental and check out everything that makes Upperville a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Delaplane Cellars (4 mi / 6.4 km)
  • RdV Vineyards (4.3 mi / 7 km)
  • Blue Valley Vineyard And Winery (7 mi / 11.3 km)
  • Naked Mountain Winery & Vineyards (7.5 mi / 12 km)
  • Bluemont Vineyard (7.7 mi / 12.4 km)
  • Greenhill Winery & Vineyards (9.9 mi / 16 km)

Exploring the natural landscape of Upperville

Whether you're an outdoor enthusiast or just want to take in the scenery, Upperville is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Blue Ridge Regional Park (6.2 mi / 10 km)
  • Glenwood Park (7.1 mi / 11.4 km)
  • Aldie Mill Historic Park (13.2 mi / 21.3 km)
  • Oatlands Historic House and Gardens (14.8 mi / 23.8 km)
  • Lake Frederick Boat Launch (14.9 mi / 24 km)
  • Shenandoah Lake Beach (15.5 mi / 24.9 km)

Transportation options to and around Upperville

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

Frequently asked questions

What is the best area to stay in Upperville, Virginia, United States of America when booking a vacation rental?
When considering a vacation rental in Upperville, Virginia, one of the best areas to explore is the charming countryside surrounding the town. This picturesque region is renowned for its stunning landscapes, rolling hills, and horse farms, making it a superb retreat for those seeking tranquility and natural beauty.

In this area, you'll find a variety of vacation rental options, from cozy cottages to luxurious estates. The ambiance is serene and inviting, ideal for relaxation and outdoor activities. One of the top attractions nearby is the historic Morven Park, which features beautiful gardens and a museum showcasing the history of the region. Additionally, the stunning views of the Blue Ridge Mountains can be appreciated from various viewpoints, offering a fantastic backdrop for nature lovers.

Another noteworthy point of interest is the Upperville Colt and Horse Show, which is one of the oldest and most prestigious equestrian events in the United States. This annual event draws visitors from far and wide, celebrating the rich equestrian tradition of the area.
How much does it cost to rent a vacation home in Upperville?
Prices for vacation rentals in Upperville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Upperville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Upperville vacation house rentals?
You can find great discounts on house rentals in Upperville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Upperville?
In Upperville, vacation houses and cottages are the most popular types of accommodations, with several options available in this picturesque area. These rentals often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy the scenic countryside. Many properties are set on expansive lots, providing outdoor spaces for relaxation and activities.
Are there any family house rentals in Upperville?
In Upperville, Virginia, there are several family-friendly house rentals available, making it a great spot for families looking to explore the beautiful countryside. The area is renowned for its charming rural atmosphere and proximity to attractions like the historic town of Middleburg, which offers quaint shops and delightful dining options. Many of these vacation homes feature spacious living rooms, fully equipped kitchens for family meals, and outdoor spaces where children can enjoy playing and exploring.

Travelers can also find properties with amenities such as game rooms, private yards, and cozy fire pits for evening gatherings. The surrounding landscape provides opportunities for outdoor activities, including hiking and horseback riding, ensuring that families can enjoy both relaxation and adventure during their stay.
Can I rent a vacation home with a pool or hot tub in Upperville?
In Upperville, Virginia, there are several vacation homes available for rent that feature pools or hot tubs, providing a relaxing escape in this picturesque setting. The area is known for its beautiful countryside, making it an ideal choice for travelers seeking a peaceful retreat. Many of these properties come with amenities such as spacious outdoor areas, fully equipped kitchens for home-cooked meals, and comfortable living spaces, superb for families or groups. Find your rental in Upperville with a pool or a hot tub.
Can I find long-stay vacation rentals in Upperville?
A long-stay vacation rental in Upperville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Upperville?
In Upperville, Virginia, there are several pet-friendly house rentals available, making it an excellent destination for travelers with furry companions. Many of these homes offer spacious layouts, private yards, and amenities like fully equipped kitchens, outdoor patios, and fireplaces, superb for family gatherings or enjoying a quiet retreat in the countryside.

The area is known for its picturesque landscapes and equestrian culture, with access to scenic trails ideal for walking or hiking with pets. Nearby, the charming town of Middleburg offers quaint shops and pet-friendly dining options, ideal for those traveling with animals.
Are there any remote work vacation rentals in Upperville?
In Upperville, Virginia, there are several vacation rentals that cater to remote work needs. This picturesque area offers tranquil surroundings, making it an ideal choice for those looking to work remotely while enjoying the beauty of the Virginia countryside. Many of the available properties come equipped with essential amenities such as high-speed internet and dedicated workspaces, including desks and private areas conducive to productivity. Some rentals may also feature free Wi-Fi, ensuring that guests can stay connected with ease. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Upperville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Upperville with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Upperville?
In Upperville, vacation rentals commonly feature a variety of amenities that enhance the stay for visitors. Most properties include fully equipped kitchens, allowing guests to prepare their meals comfortably. Additionally, many rentals offer coffee and tea makers for a convenient morning boost. Onsite parking is typically available, which is a significant advantage for those traveling by car. Many homes also come with decks or patios where guests can relax and enjoy the peaceful surroundings. Some rentals may include blenders, adding to the convenience for guests who enjoy making smoothies or other blended drinks.
When is the best time to visit Upperville for a vacation rental?
The best time to visit Upperville for a vacation rental is during the peak season from April to June, with May being particularly popular among travelers. This period invites outdoor enthusiasts and nature lovers to explore the beautiful landscapes of Virginia's horse country. Visitors can enjoy a range of activities, including horseback riding, hiking, and attending local equestrian events, all while soaking in the picturesque views of rolling hills and lush pastures.

In May, temperatures typically range from the mid-50s to the low 80s Fahrenheit, creating an ideal climate for outdoor adventures and sightseeing. The weather is generally pleasant, making it comfortable to stroll through charming local vineyards or visit nearby historic sites like the stunning Upperville Baptist Church.

For those seeking a more budget-friendly option, consider planning your trip in December. While the weather is cooler, with temperatures averaging in the low 30s to mid-40s Fahrenheit, this month offers a peaceful atmosphere, superb for a cozy getaway. You can enjoy the holiday charm of the area and explore local shops without the summer crowds.

Ultimately, your choice of visit will depend on whether you prefer the vibrant energy of the peak season filled with outdoor activities or the tranquil ambiance of the off-season, where you can enjoy the beauty of Upperville at a slower pace.
How early should I book a Upperville vacation rental?
Book your Upperville vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Upperville, Virginia, United States of America?
In Upperville, Virginia, visitors can enjoy a range of attractions that highlight the area's rich history and natural beauty. The town is known for its picturesque countryside and charming historic buildings, making it a lovely spot for leisurely strolls. The nearby Blue Ridge Mountains offer opportunities for hiking and enjoying scenic views.

Wine enthusiasts can explore the numerous wineries in the surrounding Loudoun County, many of which are just a short drive away, providing tastings and tours of their vineyards. The Upperville Colt & Horse Show, held annually, is a significant event that draws equestrian enthusiasts and showcases the area's strong equestrian culture.

Additionally, the nearby historic sites, such as the Aldie Mill and the Appalachian Trail, provide further opportunities for exploration and outdoor activities.
Can I change or cancel my Upperville home rental booking on Vrbo?
To find Upperville vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Upperville vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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