Upperville, VA
Travel Guide
Visit Upperville
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
$103 nightly
The price is $112 total per night from Sep 1 to Sep 2
$112 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,126 reviews)
"Loved this hotel Clean, friendlt staff, great breakfast and dog friendly"
Reviewed on Aug 14, 2025
Lansdowne Resort and Spa
44050 Woodridge Pkwy, Leesburg, VA
$272 nightly
The price is $310 total per night from Sep 1 to Sep 2
$310 total
Sep 1 - Sep 2
Total includes taxes and fees
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.6/10 Excellent! (1,003 reviews)
"Excellent couples getaway for Fourth of July, including great fireworks display. The pools and spa/fitness amenities are top notch and charming historic Leesburg is a 10-minute drive from the property."
Reviewed on Aug 11, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
$85 nightly
The price is $92 total per night from Aug 24 to Aug 25
$92 total
Aug 24 - Aug 25
Total includes taxes and fees
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
9/10 Wonderful! (1,002 reviews)
"Bed comfort"
Reviewed on Aug 12, 2025
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.
Breathtaking View with an Indoor Pool
Bluemont
Stay at this vacation home in Bluemont. Enjoy private pools, a fitness center, and laundry facilities. Our guests praise the pool and the helpful staff in our ...
9.6/10 Exceptional! (252 reviews)
Anniversary Celebration
"Great home and location. Back deck could use a few more umbrellas. During our stay an additional umbrella was requested and brought over very quickly. Great service. On our last day (Tuesday), there was a lot of construction noise coming from the brewery. Not sure what was going on, but it eventually ..."
Reviewed on Jul 16, 2025
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River
Front Royal
Stay at this cabin in Front Royal. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Glen Manor Vineyards and Shenandoah ...
9/10 Wonderful! (226 reviews)
"We loved our stay so much and can't wait to come back as soon as possible. The check-in process was super easy and we had a really great and relaxing stay. We even caught some catfish down at the river."
Reviewed on Aug 13, 2025
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.
Linden
Stay at this cabin in Front Royal. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Deer Lake and George Richard Thompson State Wildlife ...
10/10 Exceptional! (90 reviews)
Exactly as expected!
"The house was well designed and stocked. The space was cozy and secluded, perfect for a quiet weekend getaway."
Reviewed on Jul 14, 2025
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.
Popular places to visit
Upperville Park
Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
Explore a world of travel with Expedia
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- Honeymoon Resorts & in Middleburg
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- Visit Paris
- Paris Barns
- Sky Meadows State Park
- Delaplane Cellars
- RdV Vineyards
- Visit Rectortown
- Visit Delaplane
- Glenwood Park
- Aspen Dale Winery at the Barn
- Barrel Oak Winery
- Naked Mountain Winery & Vineyards
- Bluemont Vineyard
- Watermelon Park Campground
- Visit Middleburg
- The Boxwood Winery
- National Sporting Library & Museum
- Visit Bluemont
- Tudor Day Spa
- The Byrne Gallery
- Red Fox Fine Art
- Middleburg Vacations
- Shenandoah National Park
- Hollywood Casino at Charles Town Races
- Jiffy Lube Live
- Summit Point Motorsports Park
- Shenandoah River
- Front Royal Entrance Shenandoah National Park
- Winchester Medical Center
- Shenandoah University
- Morven Park
- George Washington National Forest
- Leesburg Corner Premium Outlets
- Potomac River
- Skyline Caverns
- Stone Tower Winery
- Bluemont Vineyard
- Tally Ho Theatre
- Museum of the Shenandoah Valley
- Apple Blossom Mall
- National Conference Center
- Morven Park
- Village at Leesburg
- The Golf Club at Lansdowne
- Breaux Vineyards
- Shenandoah Lake Beach
- King SPA
- Ashburn Park
- Shenandoah Valley Discovery Museum
- Greenhill Winery & Vineyards
- 868 Estate Vineyards
- Rock Harbor Golf Course
- Sky Meadows State Park