Upperville, VA
Travel Guide
Visit Upperville
Lansdowne Resort and Spa
44050 Woodridge Pkwy, Leesburg, VA
$252 nightly
The price is $287 total per night from Sep 1 to Sep 2
$287 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! (1,010 reviews)
"The property was beautiful….the people on staff were extremely friendly, and the rooms were very clean. Planning on staying here again in the Fall. 😊"
Reviewed on Aug 10, 2025
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
$104 nightly
The price is $113 total per night from Sep 1 to Sep 2
$113 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! (2,123 reviews)
"One of our fave places to stay when we visit Winchester."
Reviewed on Aug 10, 2025
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike, Winchester, VA
$96 nightly
The price is $104 total per night from Aug 17 to Aug 18
$104 total
Aug 17 - Aug 18
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! (1,010 reviews)
"Staff was very helpful and accommodating. Thanks so much!"
Reviewed on Aug 9, 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
Cottage on King | Charming Historic Leesburg Home
Leesburg
Book a stay at this family-friendly vacation home in Leesburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tally Ho Theatre and Edwards ...
9.4/10 Exceptional! (52 reviews)
"Charming cottage within walking distance of great restaurants in Leesburg. Enjoyed a quiet weekend away and evening strolls through the neighborhood."
Reviewed on Jul 14, 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! (225 reviews)
"The tranquility and peacefulness was just what we were looking for. We have already inquired about the other cabins and dates available. We will definitely book again! We hated to leave! 10 out of 10 stars!"
Reviewed on Jul 20, 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.
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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