Photo by Michael Gibson

Find hotels in Upperville, VA from AED 243

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Our top choices for Upperville hotels

Hilton Garden Inn Haymarket

Hilton Garden Inn Haymarket
3.0 star property
Haymarket
9.4 out of 10, Exceptional, (256)
Cozy haven near the famous concert venue, this business-friendly hotel combines convenience with comfort. Unwind in the 24-hour fitness center after exploring Haymarket IcePlex. Enjoy American cuisine at Red House Tavern and free parking during your stay.

"Nice hotel in a hallmark town "
United States
Diane
The price is AED 494
AED 573 total
includes taxes & fees
11 Jan - 12 January 2026
Hilton Garden Inn Haymarket

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (133)
Surround yourself in recreational options at this boutique B&B featuring 4 tennis courts, an outdoor pool, and an on-site restaurant. After a day on the greens, unwind at the bar or terrace. Near Waterfall Park with free parking, WiFi, and breakfast.

"Very nice cozy place and the breakfast was included and very delicious. Only issue I had was the footsteps of upstairs guests came through."
United States
Chiharu
Inn at Evergreen

Rodeway Inn & Suites Charles Town

Rodeway Inn & Suites Charles Town
2.0 star property
Charles Town
8.6 out of 10, Excellent, (1001)
Positioned near Hollywood Casino at Charles Town Races, this motel offers complimentary breakfast, WiFi, and parking. Guests can dine at Alfredo's Mediterranean restaurant on site. Harpers Ferry National Historical Park is a short drive away. Staff receives high marks for helpfulness.

"Certainly will stay again "
United States
philip
The price is AED 237
AED 268 total
includes taxes & fees
18 Jan - 19 January 2026
Rodeway Inn & Suites Charles Town

Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (48)
Enjoy local cuisine at The Conservatory, one of 2 restaurants at this charming hotel. The seasonal outdoor pool, hot tub, and terrace create a relaxing atmosphere near Glenwood Park and Middleburg Community Center.

"It was a delightful quaint exclusive country inn - a real treat to stay. "
United States
Amanda
The price is AED 1,392
AED 1,913 total
includes taxes & fees
4 Jan - 5 January 2026
Goodstone Inn & Restaurant

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (996)
Morning lap swims await in the indoor pool at this Gainesville retreat. After a free breakfast, drive 10 minutes to concerts at Jiffy Lube Live or visit Regal Virginia Gateway. Return to spacious rooms, with helpful staff ready to assist 24/7.

"We always prefer staying at this Hampton Inn when we’re in Gainesville! The accommodations are great, and the staff is excellent!"
United States
John
The price is AED 365
AED 416 total
includes taxes & fees
18 Jan - 19 January 2026
Hampton Inn by Hilton Gainesville-Haymarket

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel
3.5 star property
Old Town Winchester
9.4 out of 10, Exceptional, (1013)
Relish this Winchester hotel's Georgian charm, with an indoor pool, full-service spa, and 2 restaurants including Uno's Pizzeria for dinner. The 24-hour fitness center complements the prime location near Old Court House Civil War Museum and Bright Box Theater.

"Great hotel!"
United States
CHARLES
The price is AED 465
AED 527 total
includes taxes & fees
6 Jan - 7 January 2026
The George Washington Hotel, A Wyndham Grand Hotel

Days Inn by Wyndham Charles Town/Harpers Ferry

Days Inn by Wyndham Charles Town/Harpers Ferry
2.0 star property
Charles Town
8.0 out of 10, Very Good, (1001)
Enjoy historic exploration with a convenient base near Hollywood Casino and Harpers Ferry National Park. Free continental breakfast starts your day, while the fitness center helps maintain routines. Helpful staff and overall value make this Charles Town hotel an excellent choice.

"Nice place to stay"
United States
Cynthia
The price is AED 245
AED 277 total
includes taxes & fees
4 Jan - 5 January 2026
Days Inn by Wyndham Charles Town/Harpers Ferry

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern
4.0 star property
Downtown
9.6 out of 10, Exceptional, (410)
Discover charming comfort at this Middleburg inn offering complimentary breakfast, WiFi, and parking. Savor meals at the restaurant or enjoy drinks at the bar. The garden and terrace provide relaxing spaces near Red Fox Fine Art and the Historic District.

"Staff was super nice, room was lovely, overall an amazing stay. "
United States
Audrey
The Red Fox Inn & Tavern

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (440)
"Excellent accommodations and breakfast. "
United States
William
The price is AED 575
AED 650 total
includes taxes & fees
8 Jan - 9 January 2026
The Carriage Inn B&B

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (788)
Experience comfort at this Winchester hotel with a 24-hour fitness center and inviting indoor pool. Near Rutherford Crossing and Frederick County Fairgrounds, guests enjoy free breakfast, WiFi, and parking with attentive staff service.

"Great staff, very clean room with a good breakfast "
United States
Jim
The price is AED 393
AED 428 total
includes taxes & fees
11 Jan - 12 January 2026
SpringHill Suites by Marriott Winchester

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (2240)
Located near Apple Blossom Mall and R-C Track, this hotel offers comfortable beds praised by travelers. Enjoy complimentary breakfast, WiFi, and parking while business amenities and helpful staff ensure a pleasant stay.

"Staff is very pleasant and personable. "
United States
Julie
The price is AED 363
AED 395 total
includes taxes & fees
6 Jan - 7 January 2026
La Quinta Inn & Suites by Wyndham Winchester

Holiday Inn Express Charles Town by IHG

Holiday Inn Express Charles Town by IHG
2.5 star property
Charles Town
9.2 out of 10, Wonderful, (1004)
This welcoming hotel offers an outdoor pool for summer relaxation and complimentary breakfast to fuel adventures. Located near Charles Town Library, guests appreciate the friendly staff, free WiFi, and convenient parking for regional exploration.

"Staff was very helpful and courteous, stay here often "
United States
John
The price is AED 364
AED 411 total
includes taxes & fees
4 Jan - 5 January 2026
Holiday Inn Express Charles Town by IHG

Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville
2.5 star property
Gainesville
6.2 out of 10, (482)
Located just minutes from Jiffy Lube Live, this hotel offers free WiFi and parking for convenience. Explore nearby hiking trails after a restful night. Laundry facilities add practicality while Regal Virginia Gateway provides entertainment options.

"Amazing place "
United States
Evelyn
The price is AED 274
AED 317 total
includes taxes & fees
25 Jan - 26 January 2026
Extended Stay America Select Suites Gainesville

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (923)
"Easy check in, friendly staff, clean and quiet room. Location convenient to store."
United States
Brenda
The price is AED 393
AED 428 total
includes taxes & fees
5 Jan - 6 January 2026
Courtyard by Marriott Winchester

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North
3.0 star property
Ashburn
8.4 out of 10, Very Good, (1008)
Minutes from Washington Dulles Airport, this hotel offers a convenient free shuttle, indoor pool, and on-site dining at Great American Grill. Rooms include microwaves and refrigerators, with Lost Rhino Brewing Company just a short drive away.

"Nice stay. "
Canada
Ebrahim
The price is AED 337
AED 384 total
includes taxes & fees
5 Jan - 6 January 2026
Hilton Garden Inn Dulles North

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (175)
Savor local cuisine at La Table Provencale after swimming in the seasonal outdoor pool. This business-friendly inn provides spa services, complimentary breakfast, and free parking. Enjoy easy access to White Post Village Park while receiving attentive service from the staff.

"This B&B has been by far the loveliest, friendliest, cleanest with staff so eager to please. The rural area was so peaceful and relaxing with views of black angus in the fields. Winchester close with quaint shops. The food at the Inn was excellent. "
United States
DONNA
The price is AED 824
AED 909 total
includes taxes & fees
6 Jan - 7 January 2026
L'Auberge Provencale Inn & Restaurant

Hampton Inn Winchester N/Conference Center, VA

Hampton Inn Winchester N/Conference Center, VA
2.5 star property
Winchester
9.2 out of 10, Wonderful, (852)
Discover quiet comfort at this Winchester hotel featuring modern amenities including a seasonal outdoor pool and fitness center. Enjoy complimentary breakfast, WiFi, and parking. The attentive staff and convenient location near Eastgate Plaza Shopping Center ensure a pleasant stay.

"The room was clean, and the breakfast was plentiful. The staff was very friendly and helpful. This was the quietest stay I've had on my trips to Wincheater."
United States
Jay
The price is AED 389
AED 440 total
includes taxes & fees
5 Jan - 6 January 2026
Hampton Inn Winchester N/Conference Center, VA

Country Inn & Suites by Radisson, Winchester, VA

Country Inn & Suites by Radisson, Winchester, VA
3.0 star property
Winchester
8.8 out of 10, Excellent, (1002)
"Have stayed here multiple times -always good"
United States
Robert
The price is AED 302
AED 328 total
includes taxes & fees
25 Jan - 26 January 2026
Country Inn & Suites by Radisson, Winchester, VA

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
Tucked in Charles Town's rolling hills, this charming B&B offers pampering spa treatments and a welcoming bar. Enjoy the fitness center, stroll through garden paths, and relax on the terrace before exploring nearby Hollywood Casino and Summit Point Motorsports Park.

"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
The price is AED 561
AED 720 total
includes taxes & fees
14 Jan - 15 January 2026
Hillbrook Inn

Airlie Hotel

Airlie Hotel
3.5 star property
Warrenton
8.6 out of 10, Excellent, (334)
Discover American cuisine at Harry's restaurant, take a refreshing swim in the outdoor pool, and explore the area with free bike rentals. Near Old Jail Museum and Liberty Heritage Society Museum, this hotel offers fitness center and bar amenities.

"Gorgeous grounds. Worth the visit. "
United States
mary lynne
The price is AED 589
AED 699 total
includes taxes & fees
31 Dec - 1 January 2026
Airlie Hotel
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Stay near popular Upperville attractions

Learn more about Upperville

Hunt country elegance shines at the historic Upperville Horse Show, America's oldest running exhibition where equestrians compete each June. Wander through the quaint village to discover stone buildings, antique shops, and Sky Meadows State Park's hiking trails nearby in Paris.

Hiking Sky Meadows State Park...
Photo by Michael Gibson
Open Photo by Michael Gibson

Top Upperville Hotel Reviews

More cheap stays in Upperville

Hotels in Upperville with star-rating

Find out more about Upperville

Top reasons to visit Upperville

  • Scenic Wine Tours: Experience the beauty of Virginia's wine country with picturesque vineyards and delightful tastings.
  • Outdoor Adventures: Enjoy thrilling activities in nature, from hiking to horseback riding, perfect for outdoor enthusiasts.
  • Charming Parks: Relax at Upperville Park, ideal for leisurely strolls and family outings.
  • Historic Sites: Explore the rich history of the area through its historic houses and local attractions.
  • Cozy Accommodations: Choose from charming bed & breakfasts and unique lodging options for a memorable stay.

Find great hotels near Upperville

Discover charming lodging options in Upperville, Virginia, where you can experience the beauty of agritourism and cozy bed & breakfasts. Whether you’re seeking pet-friendly accommodations or a unique historic-themed vacation, Upperville offers a variety of hotels to suit your needs. Explore available hotels and read reviews to find the best fit for your getaway in this picturesque region of the United States.

  • DoubleTree by Hilton Front Royal Blue Ridge Shadows: Nestled in the scenic beauty of the Blue Ridge Mountains, this 4-star hotel offers a welcoming atmosphere perfect for families and business travelers alike. Just 25.7km from Upperville, guests can enjoy spacious rooms equipped with modern amenities and complimentary Wi-Fi. The hotel takes pride in being LGBTQIA-friendly, ensuring an inclusive environment. Families will appreciate the range of child-friendly services, including free cribs, making it a fantastic choice for those traveling with little ones. Relax at the on-site restaurant or take a dip in the outdoor pool, all while soaking in the stunning mountain views.
  • Hampton Inn Front Royal: Located 27.4km from Upperville, Hampton Inn Front Royal is a delightful retreat for travelers seeking a pet-friendly stay. This hotel offers a cozy atmosphere with modern comforts, including complimentary breakfast and free Wi-Fi. Its commitment to inclusivity is evident, as it warmly welcomes LGBTQIA guests and allows pets on the property, with specific policies for service animals and domestic pets. Enjoy the spacious rooms and take advantage of the fitness center to keep up with your routine. The hotel’s convenient location provides easy access to local attractions and outdoor adventures.
  • Super 8 by Wyndham Front Royal: Positioned 27.4km from Upperville, Super 8 by Wyndham Front Royal is an ideal choice for budget-conscious travelers who cherish their furry companions. This pet-friendly hotel allows dogs and provides essential amenities for a comfortable stay. Guests can enjoy complimentary breakfast and Wi-Fi in a relaxed setting. While it has restrictions on certain pets, it remains a welcoming space for service animals, ensuring all guests feel at home. The hotel’s convenient location makes it easy to explore the beautiful surroundings of Front Royal, making it a practical choice for your stay.

Where to stay near Upperville

Upperville, Virginia, offers a charming blend of outdoor adventures and romantic escapes. Explore the stunning beauty of Virginia's wine country, indulge in the luxury of nearby wineries, and unwind at Upperville Park. The town center's family-friendly atmosphere ensures a relaxing experience, while the surrounding neighborhoods provide a perfect backdrop for both romantic getaways and leisurely family vacations. Discover the unique vibes of Upperville and create unforgettable memories during your stay.

  • Middleburg: Located 12.9km from Upperville, Middleburg is a charming town known for its captivating outdoor experiences and breathtaking scenery. Visitors flock here for activities such as hiking in the nearby national parks and skiing in the winter months. With peaks in traveler arrivals during April, July, and September, this welcoming community offers a range of recreational areas and beautiful lakes to explore. Don’t miss the chance to visit local farms and vineyards that showcase the region's agricultural heritage, adding a delightful touch to your travel experience.
  • Paris: Just 6.4km away from Upperville, Paris is a picturesque town that entices visitors with its stunning outdoor landscapes and adventure opportunities. Popular among travelers from June to July and September, the area boasts various recreational facilities, including ski resorts and parks. The serene lakes and the nearby national state park make it an ideal spot for nature enthusiasts. Strolling through the quaint streets, you’ll find local shops and eateries that reflect the town’s unique charm and hospitality, making for a delightful getaway.
  • Rectortown: A quaint village located 8.0km from Upperville, Rectortown is a hidden gem for those seeking outdoor adventures and scenic views. With a peak in traveler arrivals from June to August, this community offers excellent golf courses and recreational areas for sports enthusiasts. The proximity to national and urban parks allows for leisurely hikes and picnics. Rectortown’s serene environment and friendly atmosphere make it a perfect destination for relaxation and enjoyment, providing an authentic taste of Virginia’s rural charm.

Things to do near Upperville

Upperville, Virginia, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy a variety of activities, including scenic wine tours, exciting horse shows, and thrilling outdoor adventures. The area also offers recreational parks for leisurely strolls and special events throughout the year. Don't miss the chance to pick pumpkins during the fall season, adding a charming touch to your vacation experience.

Shopping

In Upperville, visit the charming Marshall Center, just 14.5km away, offering a blend of local shops and family-friendly vibes. If you're up for a drive, Hill High Country Store is 17.7km away, while K & S Pewter, located 20.9km away, features unique handcrafted items.

Recreation

Experience the serene atmosphere at Stoneleigh Golf and Country Club, where you can enjoy a round of golf surrounded by beautiful landscapes. For a thrilling outing, head to Haymarket IcePlex for ice skating, offering fun and excitement for all ages, only a short drive away.

Adventure

At Watermelon Park Campground, located 12.9km from Upperville, immerse yourself in nature with family-friendly outdoor activities. Experience thrilling races at Summit Point Motorsports Park, 112.9km away, where adrenaline meets sports excitement. For scenic hikes, Tuckers Lane Trailhead, 17.7km from Upperville, offers breathtaking views and adventure.

Nightlife

Experience the vibrant nightlife in Upperville by catching a show at Bright Box Theater or Winchester Little Theater, both offering a blend of romance and culture. For a family-friendly movie night, Regal Fox cinema is the perfect spot, just a short drive away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Upperville

To save money on your trip to Upperville, consider visiting during the off-peak months of December to February when prices are lower. Look for hotel deals, especially on Mondays, as Saturdays can be the most expensive. Utilize Expedia’s search tool to filter by budget and type, including eco-friendly options. Combining your hotel booking with flights and activities can also lead to significant savings. Lastly, explore the area on foot to avoid public transport costs and take advantage of free local attractions.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Upperville are December to February, where the prices are slightly lower. This is in comparison to May to June and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Upperville is Monday. The most expensive day to stay in Upperville is Saturday.
  • Find cheap hotels on Expedia: Expedia’s search tool lets you set your budget, choose your ideal location, and more. You can arrange the results to display prices from lowest to highest, ensuring you find the most affordable hotels first. Additionally, you can refine your search by hotel type; for instance, selecting the Eco-certified filter will show you sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by combining your Upperville hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Upperville

Upperville, Virginia, is perfect for outdoor lovers and romantic getaways, featuring scenic parks, historic houses, and beautiful lakes. Visitors can enjoy a range of activities that cater to outdoor enthusiasts, culture seekers, and families. Nearby attractions enhance the experience, making Upperville an ideal destination for exploring nature and history while enjoying quality time with loved ones.

  • Sky Meadows State Park: Immerse yourself in the beauty of nature at Sky Meadows State Park, where scenic trails invite hiking and horseback riding amidst breathtaking landscapes. The park offers a perfect escape for outdoor enthusiasts seeking adventure and tranquility.
  • Paris Barns: Discover the charm of Paris Barns, a picturesque attraction that showcases stunning views of the surrounding countryside. It's a great spot for leisurely strolls and enjoying the serene ambiance of Virginia's rural landscape.
  • National Sporting Library & Museum: Dive into the rich heritage of sports and culture at the National Sporting Library & Museum. Explore fascinating exhibits that celebrate equestrian sports, showcasing art, literature, and historical artifacts.

Best time to go to Upperville

The best time to visit Upperville is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.8°F (-0.1°C)Light RainMostly SunnyModerately LowSlightly Low
February35.2°F (1.8°C)Light RainMostly SunnyAverageSlightly Low
March42.8°F (6.0°C)Light RainMostly SunnyAverageAverage
April53.4°F (11.9°C)Light RainMostly SunnyModerately HighAverage
May62.8°F (17.1°C)Light RainMostly SunnyModerately HighSlightly High
June71.2°F (21.8°C)Light RainMostly SunnyModerately HighSlightly High
July76.5°F (24.7°C)Light RainMostly SunnyAverageAverage
August74.3°F (23.5°C)Light RainMostly SunnyAverageAverage
September67.5°F (19.7°C)Light RainMostly SunnyAverageAverage
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

The nearest major airports for your trip to Upperville

Traveling to Upperville, Virginia, is convenient with several major airports nearby. Washington, DC (IAD-Washington Dulles International) is 38.6km away, offering hotels like Hyatt Regency Dulles and Hilton Washington Dulles Airport, both accessible within 3.2km. Washington, DC (DCA-Ronald Reagan Washington National) is 74.0km from Upperville, with nearby options such as Salamander Washington DC and Pendry Washington DC - The Wharf, both 3.2km from the airport. For those considering Manassas, VA (MNZ-Manassas Regional), located 43.5km away, Westfields Marriott and Wyndham Garden provide comfortable stays, with easy access to the airport within 17.7km and 8.0km, respectively.

Frequently asked questions

Where is the best place to stay in Upperville?
Located 21.7 mi (35 km) from the heart of Upperville, Hilton Garden Inn Dulles North is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Lansdowne Resort and Spa and Salamander Resort And Spa. See all available top hotels, or vacation rentals in Upperville.
What are some of the best vacation home rentals in Upperville?
The Apple Mountain House: This vacation home rental outside of Upperville is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. See all vacation rentals in Upperville.
If I need to cancel my hotel reservation in Upperville, will I receive a refund?
Yes, the majority of hotel bookings are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Upperville.
Where can I learn more about changing or cancelling my trip to Upperville?
To find more details about rescheduling or cancelling your trip to Upperville, head over to our customer service page.
What are some accommodations with pools in Upperville?
Hilton Garden Inn Dulles North: Features complimentary wired internet access, an indoor pool, and free self parking. Lansdowne Resort and Spa and Salamander Resort And Spa are a couple of other choices that offer an onsite pool. View all hotels with pools in Upperville.
What's the best hotel for staying near Ronald Reagan Washington National Airport (DCA)?
Hyatt Regency Crystal City is a popular 4-star hotel featuring a restaurant and an outdoor pool. It's located a short 0.6 mi (1 km) from Ronald Reagan Washington National Airport. Other options near the airport are Courtyard by Marriott Arlington Crystal City/Reagan National and Hilton Garden Inn Reagan National Airport.
What's it like staying in Upperville?
Visitors can enjoy all that Upperville has to offer including its restaurants. In Upperville, there are 6 hotels and other accommodations to choose from. Find out more about Upperville.
What are the top places to visit in Upperville?
A couple of favorite places to visit are Sky Meadows State Park and Upperville Park. You'll also find Delaplane Cellars and RdV Vineyards in the area. Check out what more to see and do in Expedia's Upperville guide.
What's the seasonal weather like in Upperville?
The hottest months are usually July and August with an average temp of 72°F, while the coldest months are January and February with an average of 37°F. Average annual precipitation for Upperville is 44 inches.

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