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Our top choices for Upperville hotels

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, (2,271 reviews)
"Room was clean, lobby and staff friendly. This is our second time staying so we always enjoy coming."
United States
Miriam
$107 nightly
The price is $117
Mar 29 - Mar 30
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,088 reviews)
"Great location; easy access off hwy. Very nice staff; clean room; comfortable beds and nice breakfast!"
United States
Theresa
$103 nightly
The price is $112
Apr 21 - Apr 22
Total with taxes and fees
Comfort Inn & Suites Winchester

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,456 reviews)
"Everything,room was amazing, staff so friendly, breakfast very good "
United States
Douglas Gary
$86 nightly
The price is $93
Mar 29 - Mar 30
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town
2.5 star property
Harpers Ferry
7.8 out of 10, Good, (1,003 reviews)
"Yes, excellent service "
United States
Luis
$89 nightly
The price is $100
Apr 16 - Apr 17
Total with taxes and fees
Clarion Inn Harpers Ferry - Charles Town

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (829 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
$93 nightly
The price is $101
Mar 29 - Mar 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Winchester

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, (870 reviews)
"The staff was wonderful! "
United States
Jayne
$106 nightly
The price is $120
Apr 18 - Apr 19
Total with taxes and fees
Hampton Inn Winchester N/Conference Center, VA

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, (1,000 reviews)
"Very accessible to restaurants and stores"
United States
Scott
$68 nightly
The price is $76
Apr 13 - Apr 14
Total with taxes and fees
Days Inn by Wyndham Charles Town/Harpers Ferry

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (948 reviews)
"Great location"
Canada
jim
$107 nightly
The price is $116
Apr 2 - Apr 3
Total with taxes and fees
Courtyard by Marriott Winchester

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,076 reviews)
"Very clean and great rates will stay again if in the area "
United States
Cindi
$71 nightly
The price is $77
Mar 28 - Mar 29
Total with taxes and fees
Travelodge by Wyndham Winchester

Home2 Suites By Hilton Winchester

Home2 Suites By Hilton Winchester
3.0 star property
Winchester
$98 nightly
The price is $111
Apr 5 - Apr 6
Total with taxes and fees
Home2 Suites By Hilton Winchester

Holiday Inn Express Winchester South-Stephens City by IHG

Holiday Inn Express Winchester South-Stephens City by IHG
2.5 star property
Stephens City
8.2 out of 10, Very Good, (839 reviews)
"Yes. Parking was great"
United States
John
$88 nightly
The price is $96
Mar 29 - Mar 30
Total with taxes and fees
Holiday Inn Express Winchester South-Stephens City by IHG

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, (1,000 reviews)
"very nice hotel,very clean"
Canada
Maria
$91 nightly
The price is $99
Apr 5 - Apr 6
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (826 reviews)
"Beautiful hotel and room. Accessible room was perfect. Staff was friendly right from check-in. Would highly recommend this hotel to anyone who needs an accessible room. "
United States
Andrew
$105 nightly
The price is $114
Apr 5 - Apr 6
Total with taxes and fees
SpringHill Suites by Marriott Winchester

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, (1,000 reviews)
"Very clean rooms and friendly staff."
United States
Christine
$91 nightly
The price is $99
Apr 16 - Apr 17
Total with taxes and fees
Country Inn & Suites by Radisson, Winchester, VA

Hampton Inn Warrenton

Hampton Inn Warrenton
2.5 star property
Warrenton
8.8 out of 10, Excellent, (167 reviews)
"Nice"
United States
Leon
$139 nightly
The price is $151
Apr 5 - Apr 6
Total with taxes and fees
Hampton Inn Warrenton

Hampton Inn & Suites Leesburg

Hampton Inn & Suites Leesburg
2.5 star property
Leesburg
8.6 out of 10, Excellent, (891 reviews)
"great breakfast and rooms were super clean. great staff and convenient location"
United States
Ronald
$98 nightly
The price is $112
Apr 5 - Apr 6
Total with taxes and fees
Hampton Inn & Suites Leesburg

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center
2.5 star property
Leesburg
8.0 out of 10, Very Good, (1,002 reviews)
"The staff is excellent"
United States
Cheray
$84 nightly
The price is $97
Apr 5 - Apr 6
Total with taxes and fees
Best Western Leesburg Hotel & Conference Center

Baymont by Wyndham Warrenton

Baymont by Wyndham Warrenton
2.5 star property
Warrenton
6.4 out of 10, (1,001 reviews)
"Quiet, clean."
United States
Karen
$69 nightly
The price is $74
Apr 5 - Apr 6
Total with taxes and fees
Baymont by Wyndham Warrenton

Hilton Garden Inn Dulles North

Hilton Garden Inn Dulles North
3.0 star property
Ashburn
8.4 out of 10, Very Good, (1,001 reviews)
"Clean rooms and a helpful friendly staff. "
United States
Cindi
$110 nightly
The price is $125
Apr 3 - Apr 4
Total with taxes and fees
Hilton Garden Inn Dulles North

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, (1,000 reviews)
"Location of hotel is great for walking to restaurants and shops. "
United States
Paul
$122 nightly
The price is $138
Apr 2 - Apr 3
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand 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.

Welcome sign to Upperville Virginia in Fauquier County.

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

  • Outdoor Adventures: Upperville is perfect for hiking, exploring parks, and enjoying the stunning countryside.
  • Wine Tours: Experience the local vineyards and taste some of Virginia's finest wines.
  • Horse Shows: Attend exciting equestrian events that showcase the region's rich horse culture.
  • Seasonal Activities: Enjoy family-friendly fun like pumpkin picking during fall.
  • Charming Accommodations: Stay in cozy bed & breakfasts or unique agritourism properties that offer local charm.

Find great hotels near Upperville

Upperville, Virginia, offers a charming selection of accommodations, including cozy bed & breakfasts and unique agritourism properties. Whether you're seeking pet-friendly options, adventure-filled stays, or a historic-themed vacation experience, you'll find a variety of hotels and vacation rentals to fit your needs. Explore the delightful lodging choices in Upperville and enjoy the perfect blend of comfort and local charm during your visit.

  • DoubleTree by Hilton Front Royal Blue Ridge Shadows: Nestled 16 miles from Upperville, DoubleTree by Hilton Front Royal Blue Ridge Shadows is a 4-star hotel that offers a unique blend of golf-themed leisure and family-friendly amenities, earning a remarkable guest rating of 9.0. Ideal for business travelers and families alike, this property features an expansive golf course where guests can enjoy a round of golf amidst the stunning Blue Ridge Mountains. Families will appreciate the dedicated children's amenities, including complimentary breakfast for kids and free cribs. With its commitment to providing quality service and a luxurious stay, this hotel is perfect for those looking to unwind and bond over a round of golf.
  • Hampton Inn Front Royal: Located 17 miles from Upperville, Hampton Inn Front Royal is a budget-friendly option that boasts a guest rating of 9.0. This hotel caters to business travelers and nature enthusiasts, offering a welcoming environment that’s also pet-friendly. Guests can enjoy the beautiful natural surroundings while taking advantage of amenities designed for wellness and comfort. The hotel allows pets and has specific policies in place to ensure a pleasant stay for furry companions. With convenient access to local parks and natural attractions, this property is perfect for those looking to explore the great outdoors without sacrificing comfort.
  • Super 8 by Wyndham Front Royal Near Shenandoah National Park: Super 8 by Wyndham Front Royal is a budget-friendly hotel situated 17 miles from Upperville, making it a great choice for pet owners seeking affordable accommodations. This property allows dogs and has specific pet policies to ensure that both guests and their furry friends feel at home. With a focus on comfort and convenience, the hotel provides easy access to Shenandoah National Park, making it an excellent base for outdoor adventures. Its inviting atmosphere and pet-friendly amenities make it an ideal spot for travelers looking to enjoy a nature-filled getaway.

Where to stay near Upperville

Discover the charm of Upperville, Virginia, a cozy country getaway perfect for outdoor enthusiasts and families alike. Explore the scenic beauty of the surrounding countryside, or indulge in a luxurious retreat in nearby Middleburg. With its welcoming atmosphere and numerous adventure opportunities, Upperville offers a delightful blend of relaxation and excitement, making it an ideal destination for those seeking a memorable vacation experience.

  • Middleburg: Located 8 miles from Upperville, Middleburg is a charming city that draws visitors year-round, especially during the peak months of April, July, and September. Known for its stunning outdoor scenery and adventurous spirit, Middleburg offers a variety of recreational options, including shopping centers and beautiful parks. Highlights include nearby national parks and scenic lakes, making it an ideal spot for nature enthusiasts and those looking to unwind in a picturesque setting.
  • Paris: Just 4 miles from Upperville, Paris is a quaint city that attracts travelers with its captivating landscapes and outdoor adventures. The best times to visit are during June to July and September, when the local charm is in full bloom. Paris features recreational areas perfect for hiking, skiing, and golfing. Visitors can explore nearby national parks and serene lakes, ensuring a delightful experience for anyone seeking a blend of relaxation and adventure in a scenic backdrop.
  • Rectortown: Situated 5 miles from Upperville, Rectortown is a picturesque village that attracts visitors with its natural beauty and outdoor activities. Peak travel seasons occur in July, August, and October, offering a welcoming atmosphere for guests. The village features recreational areas and golf courses, making it a great destination for sports enthusiasts. Local attractions include national parks and historic sites, providing a unique glimpse into the area’s rich heritage while enjoying the scenic landscapes.

Things to do near Upperville

Upperville, Virginia, is perfect for outdoor enthusiasts and adventure seekers, offering a variety of activities such as visiting local attractions, enjoying wine tours, and attending horse shows. You can also experience seasonal fun with pumpkin picking and explore recreational areas and parks. Don't miss out on the entertainment venues that add to the charm of this picturesque town.

Shopping

In Upperville, you can explore local shops featuring unique gifts and souvenirs. If you're up for a drive, check out the nearby Dulles Town Center, offering a variety of stores and dining options, or visit the historic Middleburg, known for its charming boutiques and artisan shops.

Recreation

At Sleepy Hollow Country Club, indulge in luxury wellness experiences with serene surroundings. Enjoy top-notch amenities, including spa treatments and recreational activities, all while soaking in the idyllic countryside atmosphere. Perfect for relaxation and rejuvenation, this venue offers an elegant escape from everyday life.

Adventure

In Upperville, explore the scenic trails of the Appalachian Trail for hiking and breathtaking views. Experience thrilling horseback riding at local stables, or go wine tasting at nearby vineyards, savoring exquisite Virginia wines while enjoying picturesque landscapes.

Nightlife

In Upperville, the nightlife is charming and laid-back. Enjoy a cozy evening at the local wine bars, where you can savor Virginia wines. For a lively atmosphere, check out nearby pubs offering live music and friendly conversations, perfect for unwinding after a day of exploration.

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

Booking tips and Expedia advantages for Upperville

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Upperville are January to March, 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: Utilize Expedia's search tool to refine your preferences, such as your budget, desired location, and preferred hotel type. To find the most affordable prices and deals, simply arrange the price filter from lowest to highest.
  • 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 enthusiasts and adventure seekers. Visitors can enjoy stunning scenery while exploring popular attractions like urban parks, serene lakes, and local galleries. Whether you're looking for a family-friendly outing or a cultural experience, Upperville offers a variety of points of interest that cater to all types of travelers, making it an ideal vacation destination.

  • Sky Meadows State Park: Located 4 miles from Upperville, Sky Meadows State Park offers stunning natural scenery and a variety of outdoor adventures. Enjoy hiking trails that wind through lush landscapes, perfect for nature lovers and those seeking a peaceful escape.
  • Dinosaur Land: A fun-filled theme park situated 14 miles away, Dinosaur Land is a whimsical destination for families. Featuring life-sized dinosaur sculptures and playful attractions, it promises a day of entertainment for visitors of all ages.
  • Paris Barns: Just 4 miles from Upperville, Paris Barns is a charming attraction that showcases picturesque scenery. Whether you're exploring the grounds or enjoying a leisurely stroll, it's an idyllic spot for relaxation and scenic views.

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 SunnyAverageSlightly Low
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 LowAverage

The nearest major airports for your trip to Upperville

Traveling to Upperville, Virginia is convenient with access to major airports including Washington, DC (DCA-Ronald Reagan Washington National), located 46 miles away, and Washington, DC (IAD-Washington Dulles Intl.), just 24 miles away. Nearby hotels at DCA include the 5-star InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 2 miles away. At IAD, options include the 4-star Westin Washington Dulles Airport and the Washington Dulles Airport Marriott, both within a mile. For those considering Baltimore, MD (BWI-Baltimore Washington Intl.), located 67 miles away, the 5-star Pendry Baltimore and Four Seasons Hotel Baltimore are excellent CHOices, situated 8 miles from the airport.

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 $76 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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