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Our top choices for Upperville hotels

1. Salamander Middleburg

Salamander Middleburg
5.0 star property
Middleburg
9.2 out of 10, Wonderful, (429 reviews)
"Very close to DC. Service was great."
United States
Eva
27 days ago
$728 nightly
The price is $830
Nov 30 - Dec 1
Total with taxes and fees
Salamander Middleburg

2. Lansdowne Resort and Spa

Lansdowne Resort and Spa
4.0 star property
Leesburg
9.0 out of 10, Wonderful, (1,000 reviews)
"Went to Lansdowne for a last minute girls trip. The spa was our favorite part."
United States
Hannah
12 days ago
$225 nightly
The price is $257
Nov 22 - Nov 23
Total with taxes and fees
Lansdowne Resort and Spa

3. 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, (1,006 reviews)
"The property was clean. The bar was great."
United States
Christine
1 day ago
$130 nightly
The price is $148
Nov 19 - Nov 20
Total with taxes and fees
The George Washington Hotel, A Wyndham Grand Hotel

4. 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)
"We loved the location close to some shops."
United States
Mary
4 days ago
$104 nightly
The price is $115
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Winchester

5. The Red Fox Inn & Tavern

The Red Fox Inn & Tavern
4.0 star property
Downtown
9.6 out of 10, Exceptional, (462 reviews)
"Parking is complimentary. The location is perfect for walking around Middleburg."
United States
Michael
August 23rd, 2026
$513 nightly
The price is $585
Nov 15 - Nov 16
Total with taxes and fees
The Red Fox Inn & Tavern

6. Goodstone Inn & Restaurant

Goodstone Inn & Restaurant
4.0 star property
Middleburg
9.6 out of 10, Exceptional, (58 reviews)
"Charming and delicious and perfect getaway!!"
United States
Karlyn
12 days ago
$388 nightly
The price is $443
Nov 30 - Dec 1
Total with taxes and fees
Goodstone Inn & Restaurant

7. TRU By Hilton Winchester

TRU By Hilton Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,003 reviews)
"Rooms good sized, beds comfortable, quiet slept great , great breakfast."
United States
Jesse
2 days ago
$81 nightly
The price is $90
Nov 22 - Nov 23
Total with taxes and fees
TRU By Hilton Winchester

8. Spark by Hilton Winchester

Spark by Hilton Winchester
3.0 star property
Winchester
9.2 out of 10, Wonderful, (1,009 reviews)
"The hotel was amazing for value."
Canada
Lawrence R
5 days ago
$65 nightly
The price is $73
Dec 6 - Dec 7
Total with taxes and fees
Spark by Hilton Winchester

9. 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, (1,007 reviews)
"Hotel was clean. Staff was helpful and friendly. We enjoyed our stay."
United States
Debra
15 days ago
$102 nightly
The price is $113
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Winchester Se-Historic Gateway by IHG

10. The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino
3.0 star property
Charles Town
8.6 out of 10, Excellent, (657 reviews)
"Staff were all very nice. Breakfast was good. The property was clean."
United States
Rebecca
10 days ago
$97 nightly
The price is $108
Nov 30 - Dec 1
Total with taxes and fees
The Inn at Charles Town - Hollywood Casino

11. La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport
3.0 star property
Yorkshire
8.6 out of 10, Excellent, (1,002 reviews)
"Evening desk clerk was extremely helpful."
United States
Paul
15 days ago
$91 nightly
The price is $104
Nov 29 - Nov 30
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

12. Holiday Inn Chantilly - Dulles Arpt Area by IHG

Holiday Inn Chantilly - Dulles Arpt Area by IHG
3.0 star property
Chantilly
8.4 out of 10, Very good, (1,010 reviews)
"I enjoyed my stay very much."
United States
christy
6 days ago
$91 nightly
The price is $105
Dec 10 - Dec 11
Total with taxes and fees
Holiday Inn Chantilly - Dulles Arpt Area by IHG

13. Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester
2.5 star property
Winchester
9.2 out of 10, Wonderful, (1,448 reviews)
"Perfect accommodation great breakfast and attentive gracious staff."
United States
Kathleen
11 days ago
$82 nightly
The price is $91
Nov 12 - Nov 13
Total with taxes and fees
Microtel Inn & Suites by Wyndham Winchester

14. Embassy Suites by Hilton Dulles North Loudoun

Embassy Suites by Hilton Dulles North Loudoun
3.5 star property
Ashburn
8.6 out of 10, Excellent, (1,003 reviews)
"Wonderful hotel will always stay there."
United States
Gary
9 days ago
$142 nightly
The price is $162
Dec 6 - Dec 7
Total with taxes and fees
Embassy Suites by Hilton Dulles North Loudoun

15. Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester
2.5 star property
Winchester
9.4 out of 10, Exceptional, (1,153 reviews)
"Convenient to the highway and reasonably priced."
United States
Donna S.
3 days ago
$100 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Comfort Inn & Suites Winchester

16. 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, (1,008 reviews)
"It was a nice stay.. Third time staying relaxing and peaceful."
United States
Adrian
8 days ago
$118 nightly
The price is $130
Dec 6 - Dec 7
Total with taxes and fees
DoubleTree by Hilton Front Royal Blue Ridge Shadows

17. Hampton Inn Washington-Dulles Int'l Airport South

Hampton Inn Washington-Dulles Int'l Airport South
2.5 star property
Chantilly
9.0 out of 10, Wonderful, (1,005 reviews)
"The staff were very helpful and accommodating."
United Kingdom
Mary
7 days ago
$111 nightly
The price is $126
Nov 28 - Nov 29
Total with taxes and fees
Hampton Inn Washington-Dulles Int'l Airport South

18. Comfort Suites Manassas Battlefield Park

Comfort Suites Manassas Battlefield Park
2.5 star property
Sudley
8.0 out of 10, Very good, (1,009 reviews)
"Rooms are always clean. Staff is very friendly. I visit VA."
United States
MUHAMMAD
8 days ago
$88 nightly
The price is $101
Nov 23 - Nov 24
Total with taxes and fees
Comfort Suites Manassas Battlefield Park

19. Hotel Burg

Hotel Burg
4.0 star property
Leesburg's Old and Historic District
9.6 out of 10, Exceptional, (137 reviews)
"Beautiful rooms, friendly staff, great amenities, and the perfect location."
United States
Melanie
7 days ago
$245 nightly
The price is $282
Nov 29 - Nov 30
Total with taxes and fees
Hotel Burg

20. Hillbrook Inn

Hillbrook Inn
4.0 star property
Charles Town
9.2 out of 10, Wonderful, (693 reviews)
"The soaking tub was quite nice. The staff were absolutely excellent."
United States
Aaron
11 days ago
$174 nightly
The price is $192
Nov 22 - Nov 23
Total with taxes and fees
Hillbrook Inn
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.

Where to stay near Upperville

Upperville, a picturesque town, offers a delightful blend of outdoor adventures and scenic beauty. Explore the charming upperville areas and the nearby historic Shepherdstown. With family-friendly vibes and a relaxing atmosphere, you're sure to enjoy the perfect getaway in this enchanting region, including the inviting western Fairfax.

Middleburg

For travelers seeking a memorable getaway, Middleburg offers a charming blend of culture and nature that enchants every visitor. Explore the historic streets of the Middleburg Historic District, immerse yourself in the art at Red Fox Fine Art, and enjoy the serene landscapes of Aldie Mill Historic Park. With its appeal for outdoor and adventure lovers, Middleburg is only about 8 miles by car from Upperville, making it an ideal spot for a relaxing stay. Choosing Middleburg for your accommodations ensures a delightful experience in Virginia's scenic countryside.

Paris

Experience the charm of Paris, Virginia, an excellent hub for nature lovers and history enthusiasts eager to explore attractions such as Sky Meadows State Park, Myron Glaser Cabin Tract, and the unique Paris Barns. This delightful destination offers a blend of outdoor adventures and scenic beauty, making it perfect for a weekend getaway or a refreshing retreat. Located about a 4-mile drive from Upperville, Paris is a smart choice for travelers looking to unwind and immerse themselves in the local culture.

Rectortown

If you are a nature enthusiast or a family looking for a weekend getaway, make your vacation planning effortless by staying in Rectortown. This charming village, located about 7 miles by car from Upperville, offers easy access to stunning outdoor experiences, including Sky Meadows State Park and Sherwood Lake. Enjoy the scenic beauty while exploring the historic Middleburg Historic District. Rectortown is a smart choice for those seeking adventure and tranquility in a picturesque setting.

Delaplane

Immerse yourself in Delaplane, where weekend getaway enthusiasts can easily access the stunning Sky Meadows State Park and the charming Paris Barns. This picturesque destination offers a perfect blend of outdoor adventure and scenic beauty, making it an ideal choice for those seeking nature and wine experiences. Located about 6 miles by car from Upperville, Delaplane is a smart choice for travelers looking to unwind and explore the surrounding natural attractions.

Bloomfield

Travelers visiting the area often choose Bloomfield, especially families and nature enthusiasts seeking close proximity to outdoor adventures and local charm. In Bloomfield, you can explore the scenic Blue Ridge Regional Park, enjoy fresh produce at Great Country Farms, and immerse yourself in the rich history of the Middleburg Historic District. Located about 10 miles by car from Upperville, Bloomfield offers a tranquil retreat that makes for an excellent hotel booking choice, perfect for a memorable getaway.

Stay near popular Upperville attractions

Upperville is a hidden gem for outdoor enthusiasts and culture seekers alike. With attractions on Upperville, including scenic parks and galleries, visitors can explore the charming Upperville center or venture to the historic Antietam Battlefield, making your stay both adventurous and enriching.

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.

A sign for the Village of UPPERVILLE with a 'Please drive slowly' message.

Top Upperville Hotel Reviews

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.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
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 much is the nightly rate at a Upperville hotel?

Prices for hotels in Upperville often vary, but you can find a great deal from $67 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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