Photo by Michael Gibson

Find hotels in Upperville, VA from $66

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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, (255)
"Nice hotel in a hallmark town "
United States
Diane
$133 nightly
The price is $154
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Haymarket

Inn at Evergreen

Inn at Evergreen
3.5 star property
Haymarket
9.4 out of 10, Exceptional, (132)
"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
$263 nightly
The price is $300
Jan 12 - Jan 13, 2026
Total with taxes and fees
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, (1003)
"Certainly will stay again "
United States
philip
$64 nightly
The price is $72
Jan 11 - Jan 12, 2026
Total with taxes and fees
Rodeway Inn & Suites Charles Town

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, (1000)
"Nice place to stay"
United States
Cynthia
$66 nightly
The price is $74
Dec 28 - Dec 29
Total with taxes and fees
Days Inn by Wyndham Charles Town/Harpers Ferry

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, (1005)
"Great hotel!"
United States
CHARLES
$127 nightly
The price is $143
Jan 1 - Jan 2, 2026
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel

Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (48)
"It was a delightful quaint exclusive country inn - a real treat to stay. "
United States
Amanda
$457 nightly
The price is $521
Dec 29 - Dec 30
Total with taxes and fees
Goodstone Inn & Restaurant

The Carriage Inn B&B

The Carriage Inn B&B
3.5 star property
Charles Town
9.6 out of 10, Exceptional, (439)
"Excellent accommodations and breakfast. "
United States
William
$155 nightly
The price is $176
Jan 5 - Jan 6, 2026
Total with taxes and fees
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)
"Great staff, very clean room with a good breakfast "
United States
Jim
$107 nightly
The price is $117
Jan 4 - Jan 5, 2026
Total with taxes and fees
SpringHill Suites by Marriott Winchester

Hampton Inn by Hilton Gainesville-Haymarket

Hampton Inn by Hilton Gainesville-Haymarket
2.5 star property
Gainesville
8.8 out of 10, Excellent, (993)
"Friendly staff, clean room, good breakfast "
United States
Vivian
$99 nightly
The price is $113
Jan 11 - Jan 12, 2026
Total with taxes and fees
Hampton Inn by Hilton Gainesville-Haymarket

The Red Fox Inn & Tavern

The Red Fox Inn & Tavern
4.0 star property
Downtown
9.6 out of 10, Exceptional, (408)
"Staff was super nice, room was lovely, overall an amazing stay. "
United States
Audrey
$335 nightly
The price is $382
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Red Fox Inn & Tavern

Extended Stay America Select Suites Gainesville

Extended Stay America Select Suites Gainesville
2.5 star property
Gainesville
6.2 out of 10, (480)
"Amazing place "
United States
Evelyn
$83 nightly
The price is $94
Jan 1 - Jan 2, 2026
Total with taxes and fees
Extended Stay America Select Suites Gainesville

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, (2234)
"The place was clean, super friendly front desk staff, SO pet friendly with such a reasonable pet fee, and overall reasonable rate. Would 100% stay here again if I came back through this town. "
United States
Jordyn
$99 nightly
The price is $107
Dec 28 - Dec 29
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (919)
"comfortable room, amenities and staff"
United States
Prashant
$107 nightly
The price is $116
Jan 1 - Jan 2, 2026
Total with taxes and fees
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, (1000)
"Nice stay. "
Canada
Ebrahim
$92 nightly
The price is $104
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hilton Garden Inn Dulles North

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, (1000)
"Nice place to stay "
United States
Wendy
$99 nightly
The price is $112
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Charles Town by IHG

Salamander Resort And Spa

Salamander Resort And Spa
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (374)
"."
Canada
Ivanti
$555 nightly
The price is $632
Jan 5 - Jan 6, 2026
Total with taxes and fees
Salamander Resort And Spa

Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
8.6 out of 10, Excellent, (671)
"We had a wonderful time at Hillbrook. Loved the grounds, the cozy room, the spa massage was awesome!"
United States
Nataliya
$171 nightly
The price is $189
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hillbrook Inn

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
$82 nightly
The price is $90
Jan 25 - Jan 26, 2026
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA

L'Auberge Provencale Inn & Restaurant

L'Auberge Provencale Inn & Restaurant
4.0 star property
Boyce
9.6 out of 10, Exceptional, (174)
"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
$229 nightly
The price is $253
Jan 4 - Jan 5, 2026
Total with taxes and fees
L'Auberge Provencale Inn & Restaurant

Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1000)
"Great room cozy bed fabulous restaurant great staff on property"
United States
joyce
$85 nightly
The price is $92
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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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 exquisite vintages of the nearby wine country, perfect for wine enthusiasts.
  • Thrilling Horse Shows: Attend exciting equestrian events that showcase the region's rich horse culture.
  • Outdoor Adventures: Enjoy hiking and exploring beautiful parks and lakes ideal for nature lovers.
  • Charming Local Culture: Visit Upperville Center for a taste of local shops, dining, and seasonal activities.
  • Cozy Accommodations: Choose from inviting bed and breakfasts and unique agritourism properties for a memorable stay.

Find great hotels near Upperville

Discover the charm of Upperville, Virginia, where a variety of cozy accommodations await you. From inviting bed and breakfast options to unique agritourism properties, there's something for every traveler. Whether you're seeking a pet-friendly getaway or a historic-themed vacation experience, Upperville has you covered. Explore available hotels, read reviews, and find the best lodging near this picturesque destination for an unforgettable stay.

  • DoubleTree by Hilton Front Royal Blue Ridge Shadows: Experience a blend of luxury and leisure at DoubleTree by Hilton Front Royal Blue Ridge Shadows, a 4-star hotel ideally situated 16 miles from Upperville. This property is perfect for those seeking a golf-themed getaway, offering a stunning golf course right on-site. The hotel caters to business travelers with amenities like a 24-hour business center, meeting rooms, and a conference center. As an LGBTQIA-friendly establishment, it provides an inclusive environment for all guests. Enjoy a comfortable stay while taking advantage of the picturesque Blue Ridge views and exceptional service.
  • Super 8 by Wyndham Front Royal: Affordable and welcoming, Super 8 by Wyndham Front Royal is located 17 miles from Upperville and is perfect for pet lovers. This pet-friendly hotel allows dogs and provides a comfortable space for your furry friends with specific amenities designed to ensure a pleasant stay for both pets and their owners. Guests appreciate the convenient location and simple, clean accommodations, making it a practical choice for budget-conscious travelers looking for a hassle-free experience while exploring the area.
  • Hampton Inn Front Royal: Nestled 17 miles from Upperville, Hampton Inn Front Royal combines comfort with a nature-themed ambiance, making it an ideal choice for outdoor enthusiasts. This hotel is LGBTQIA welcoming and features modern business amenities including an accessible business center and meeting rooms, ensuring a productive stay for professionals. Guests rave about the warm hospitality and convenient access to nearby natural attractions, making it a perfect blend for leisure and work travelers alike.

Where to stay near Upperville

Upperville, Virginia, is a hidden gem for outdoor enthusiasts and families alike. Explore the scenic Upperville Park, where stunning landscapes await. The charming Upperville Center offers a taste of local culture, while the nearby wine country invites you to sample exquisite vintages. Discover the beauty of Virginia through leisurely hikes and relaxing retreats, all while enjoying a friendly and welcoming atmosphere that perfectly blends adventure and relaxation.

  • Middleburg: Nestled 8 miles from Upperville, Middleburg is a charming town known for its scenic landscapes and outdoor adventures. Visitors flock here year-round, with peaks in April, July, and September, drawn by its recreational areas and shopping options. The town’s proximity to national and state parks offers ample opportunities for hiking and enjoying nature. Notable attractions include picturesque lakes and stunning vistas that make Middleburg a perfect spot for nature lovers and those seeking an invigorating escape.
  • Paris: Located just 4 miles from Upperville, Paris is a quaint town that captivates travelers with its breathtaking scenery and outdoor activities. The peak visiting seasons in June, July, and September attract enthusiasts looking for adventures ranging from camping to skiing. With nearby national parks and lakes, visitors can immerse themselves in nature while enjoying recreational areas. Paris provides a serene backdrop for relaxation and exploration, making it a delightful stop on your Virginia itinerary.
  • Rectortown: A short 5 miles from Upperville, Rectortown is a charming village perfect for adventure seekers and sports enthusiasts. The village sees a rise in visitors from May to July, who come to enjoy skiing and various outdoor activities. With access to national parks and recreational areas, Rectortown offers a unique blend of outdoor sports and natural beauty. Whether you’re hitting the slopes or enjoying a leisurely day in the park, this village promises an engaging experience for all visitors.

Things to do near Upperville

Upperville, Virginia, offers a delightful mix of outdoor adventures and local charm. Visitors can enjoy scenic wine tours, attend thrilling horse shows, and explore recreational areas. Seasonal activities like pumpkin picking add to the fun, while various special events throughout the year provide opportunities for unique experiences. Whether shopping at local centers or soaking in the beautiful landscapes, Upperville promises an enjoyable getaway for all outdoor enthusiasts.

Shopping

For shopping in Upperville, visit Marshall Center, located 9 miles away, offering a family-friendly vibe. If you're up for a drive, check out Hill High Country Store, 11 miles away, or K & S Pewter, 13 miles away, both providing unique gifts and souvenirs.

Recreation

At Stoneleigh Golf and Country Club, enjoy a round of golf amidst picturesque landscapes, perfect for relaxation and camaraderie. Fireman's Field offers a vibrant atmosphere for sports enthusiasts, while Haymarket IcePlex provides thrilling ice skating adventures, blending fun and fitness for an unforgettable experience.

Adventure

At Watermelon Park Campground, 8 miles from Upperville, enjoy outdoor adventures like fishing and kayaking in a family-friendly atmosphere. For adrenaline junkies, Summit Point Motorsports Park, located 18 miles away, offers thrilling motor racing experiences. Explore the scenic beauty of Tuckers Lane Trailhead, 11 miles from Upperville, perfect for hiking enthusiasts.

Nightlife

In Upperville, the nightlife is vibrant with options like Bright Box Theater and Winchester Little Theater, both offering a mix of culture and romance just 20 miles away. For movie lovers, Regal Fox cinema, located 19 miles away, provides an entertaining escape with a romantic atmosphere.

*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 between December and February, when accommodation prices are lower. Monday is the cheapest day to stay, while Saturday is the priciest. Use Expedia to search for budget-friendly hotels and take advantage of package deals that combine flights, hotels, and activities. Joining Expedia's One Key membership can provide exclusive discounts and allow you to earn OneKeyCash for future stays. Additionally, explore free activities in the area to enhance your experience without overspending.

  • 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 customize your search based on your budget, desired location, and additional preferences. You can easily arrange the results to display hotels from the lowest to highest price, ensuring you find the most affordable options first. Additionally, you have the option to refine your search by hotel category; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that you can book.
  • Consider bundling your trip: You can save money by combining your hotel stay in Upperville with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Upperville

Upperville, Virginia, is an ideal destination for those seeking outdoor adventures and scenic beauty. Visitors can explore urban parks, picturesque lakes, and historic houses that offer a glimpse into the area's rich culture. With activities suitable for families and nature lovers alike, Upperville promises memorable experiences. Additionally, nearby attractions provide even more opportunities for exploration and enjoyment during your stay.

  • Sky Meadows State Park: This scenic national park offers stunning views, hiking trails, and opportunities for outdoor adventures. With its rolling hills and meadows, it's perfect for nature enthusiasts looking to explore Virginia's beautiful landscapes.
  • Paris Barns: A charming attraction, Paris Barns provides picturesque scenery and a relaxing atmosphere. It's an ideal spot for a leisurely stroll or enjoying a picnic while taking in the serene countryside views.
  • Morven Park: A historic estate that showcases Virginia's rich culture and heritage. Visitors can explore the beautiful gardens, historic mansion, and equestrian facilities, making it a fascinating destination for history buffs and families alike.

Best time to go to Upperville

The best time to visit Upperville can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Upperville falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Upperville falls in January, 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 via several major airports. Washington, DC (DCA-Ronald Reagan Washington National) is located 46 miles away, with nearby hotels such as the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 2 miles from the airport. Washington, DC (IAD-Washington Dulles Intl.) is 24 miles away, offering hotel options like Hyatt Regency Dulles and The Westin Washington Dulles Airport, both just 1 mile from the airport. For those flying into Manassas, VA (MNZ-Manassas Regional), located 27 miles from Upperville, nearby hotels include Westfields Marriott Washington Dulles and Wyndham Garden Manassas, 11 miles and 5 miles away respectively.

Frequently asked questions

What is the best area to stay in Upperville?
The best area to stay in Upperville is directly within the village center, as it offers the most convenient access to local attractions and a peaceful environment.

Upperville's village center is characterized by its historic stone and brick buildings, equestrian estates, and rolling hills. The main thoroughfare, John S. Mosby Highway (Route 50), runs directly through the village, with most establishments clustered around it. This area provides a tranquil setting, ideal for couples seeking a peaceful getaway.

Couples will appreciate the village center's proximity to local vineyards and equestrian events, providing a relaxed yet engaging experience.
When is the best time to go to Upperville?
The best time to visit Upperville is during the spring (late April to early June) and fall (mid-September to late October) when the weather is most pleasant.

Spring in Upperville brings mild temperatures and blooming landscapes, making it ideal for exploring the rolling hills and horse country. This season is particularly appealing for couples who enjoy scenic drives, horseback riding, or visiting local vineyards, as the countryside is at its most picturesque. The Upperville Colt & Horse Show, a prominent equestrian event, also takes place in early June, drawing many visitors.

Fall offers crisp air, vibrant foliage, and comfortable temperatures great for outdoor activities. Travelers looking for a relaxing getaway will appreciate the stunning autumn colors, which provide a beautiful backdrop for exploring the area's historic sites and enjoying farm-to-table dining.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Upperville.
How can I save on a Upperville hotel booking with Expedia?
With Expedia, you earn OneKeyCash™* on eligible Upperville hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It's free to join, and you'll unlock our lowest Member Prices as soon as you're signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Upperville hotel?
Prices for hotels in Upperville often vary, but you can find a great deal from $66 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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