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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, (2,246 reviews)
"yes, room was spotless very nice place to stay"
United States
ROBERT
The price is AED 337
AED 367 total
includes taxes & fees
19 Jan - 20 Jan
La Quinta Inn & Suites by Wyndham Winchester

Quality Inn Winchester

Quality Inn Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,003 reviews)
"Great stay, as usual"
United States
Mary
The price is AED 305
AED 331 total
includes taxes & fees
6 Feb - 7 Feb
Quality Inn Winchester

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,096 reviews)
"We have stayed here many times on our way to Massachusetts and find it perfect every time."
United States
Patsy
The price is AED 360
AED 392 total
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites 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, (1,001 reviews)
"Clean efficient room with good front desk service. Convienence to Highway 81 and eateries."
United States
Chris
The price is AED 300
AED 327 total
includes taxes & fees
1 Feb - 2 Feb
Country Inn & Suites by Radisson, Winchester, VA

Super 8 by Wyndham Front Royal Near Shenandoah National Park

Super 8 by Wyndham Front Royal Near Shenandoah National Park
2.0 star property
Front Royal
7.6 out of 10, Good, (1,001 reviews)
"Good condition "
United States
Phillip
The price is AED 228
AED 253 total
includes taxes & fees
19 Jan - 20 Jan
Super 8 by Wyndham Front Royal Near Shenandoah National Park

SpringHill Suites by Marriott Winchester

SpringHill Suites by Marriott Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (798 reviews)
"Great stay!"
United States
Rene
The price is AED 372
AED 404 total
includes taxes & fees
1 Feb - 2 Feb
SpringHill Suites by Marriott Winchester

Holiday Inn Express Hotel & Suites Warrenton by IHG

Holiday Inn Express Hotel & Suites Warrenton by IHG
2.5 star property
Warrenton
8.6 out of 10, Excellent, (776 reviews)
"Convenient location for my business trip spacious, and clean, thank you"
United States
Robert
The price is AED 316
AED 345 total
includes taxes & fees
22 Jan - 23 Jan
Holiday Inn Express Hotel & Suites Warrenton by IHG

Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (1,003 reviews)
"Good hotel on our road trip"
United States
Janet
The price is AED 283
AED 321 total
includes taxes & fees
8 Feb - 9 Feb
Spark by Hilton Winchester

Fairfield Inn & Suites by Marriott Winchester

Fairfield Inn & Suites by Marriott Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (815 reviews)
"We stay here a lot and it is always consistently clean and service is great. "
United States
Kim
The price is AED 340
AED 370 total
includes taxes & fees
20 Jan - 21 Jan
Fairfield Inn & Suites by Marriott Winchester

Courtyard by Marriott Winchester

Courtyard by Marriott Winchester
3.0 star property
Winchester
9.0 out of 10, Wonderful, (927 reviews)
"Room was great. Staff was extremely friendly."
United States
Amy
The price is AED 372
AED 404 total
includes taxes & fees
23 Jan - 24 Jan
Courtyard by Marriott 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)
"Overall, this hotel was clean, quiet, a good option to explore Harper's Ferry. "
United States
Jessie
The price is AED 328
AED 367 total
includes taxes & fees
25 Jan - 26 Jan
Clarion Inn Harpers Ferry - Charles Town

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,433 reviews)
"Clean room and bathroom, friendly staff, helpful."
United States
Thomas
The price is AED 300
AED 326 total
includes taxes & fees
26 Jan - 27 Jan
Microtel Inn & Suites by Wyndham Winchester

TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.0 out of 10, Wonderful, (788 reviews)
"Clean room, good breakfast, easy check in/out."
United States
Joseph
The price is AED 286
AED 311 total
includes taxes & fees
26 Jan - 27 Jan
TRU By Hilton Winchester

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, (1,003 reviews)
"Nice clean room, friendly staff, and the restaurant was very good."
United States
Susan
The price is AED 286
AED 323 total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Winchester Se-Historic Gateway by IHG

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, (855 reviews)
"Super clean room comfy beds"
United States
Joy
The price is AED 389
AED 440 total
includes taxes & fees
24 Jan - 25 Jan
Hampton Inn Winchester N/Conference Center, VA

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester
2.5 star property
Winchester
8.6 out of 10, Excellent, (1,066 reviews)
"Hotels well Located off 81 for a nice pull Off and overnight stay. Staff is friendly and helpful and rooms comfortable and quiet. "
United States
Stefanie
The price is AED 257
AED 280 total
includes taxes & fees
19 Jan - 20 Jan
Travelodge by Wyndham 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, (813 reviews)
"Clean room, nice staff, simple but good breakfast, fresh ground coffee machine was really nice. "
United States
Rose
The price is AED 272
AED 296 total
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Winchester South-Stephens City by IHG

DoubleTree by Hilton Front Royal Blue Ridge Shadows

DoubleTree by Hilton Front Royal Blue Ridge Shadows
4.0 star property
Front Royal
9.0 out of 10, Wonderful, (1,001 reviews)
"Great room and staff. Nice restaurant and bar also with good prices. Very nice hotel. 5 stars"
United States
Vincent
The price is AED 358
AED 395 total
includes taxes & fees
25 Jan - 26 Jan
DoubleTree by Hilton Front Royal Blue Ridge Shadows

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, (1,007 reviews)
"Great hotel!"
United States
CHARLES
The price is AED 465
AED 527 total
includes taxes & fees
25 Jan - 26 Jan
The George Washington Hotel, A Wyndham Grand Hotel

Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University
2.5 star property
Winchester
7.8 out of 10, Good, (1,000 reviews)
"great stay with breakfast too"
United States
James
The price is AED 281
AED 306 total
includes taxes & fees
26 Jan - 27 Jan
Sleep Inn & Suites Winchester near University
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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 22.8 mi (36.7 km) from the heart of Upperville, Lansdowne Resort and Spa is a top choice for your stay based on our traveler data. Other good choices for your stay in the area are Hilton Garden Inn Dulles North 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?
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry: This vacation home rental outside of Upperville is located in the mountains and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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?
Lansdowne Resort and Spa: Features a seasonal outdoor pool, an indoor pool, and 3 outdoor tennis courts. Hilton Garden Inn Dulles North 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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