Upperville Vacation Rentals
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Vacation Rentals in Upperville
Breathtaking views with an indoor private pool, come escape with us
Located in Bluemont, this vacation home is in the mountains, a 3-minute drive from Twin Oaks Tavern Winery and 6 minutes from Hill High Country Store.
Terra Alta - Incredible River Views and Hot Tub!
With a stay at this vacation home in Charles Town, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and Shenandoah River.
Hot Tub
Kitchen
Charles Town Home w/ Private Pool & Hot Tub
With a stay at this vacation home in Charles Town, you'll be within a 10-minute drive of Hollywood Casino at Charles Town Races and Locust Hill Golf Course.
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
Located in Marshall, this vacation home is in a rural location, within a 10-minute drive of Upperville Park and National Sporting Library & Museum.
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Located in Middleburg, this vacation home is in a rural location, a 5-minute drive from Greenhill Winery & Vineyards and 5 minutes from Red Fox Fine Art.
The PINK PEARL in Historic Leesburg
A stay at this vacation home places you in the heart of Leesburg, steps from Catoctin Valley and 7 minutes by foot from Raflo Park.
Stunning House! Minutes From Shenandoah River
Located in Harpers Ferry, this vacation home is on a lake, a 4-minute drive from Shenandoah River and 6 minutes from Shenandoah Lake Beach.
Cozy Country Getaway in the Heart of Upperville
Located in Upperville, this vacation home is a 1-minute drive from Upperville Park and 8 minutes from Paris Barns.
Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country
The price is $574 per night
$574
includes taxes & fees
$540 per night
Jan 14 - Jan 15, 2025
Free Cancellation
Located in Marshall, this vacation home is in the mountains, a 4-minute drive from Marshall Center and 6 minutes from Northern Fauquier Community Park.
Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA
With a stay at this vacation home in Berryville, you'll be within a 5-minute drive of Shenandoah River and 612 Vineyard.
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.
Upperville Vacation Rentals essential information
Accommodation | 194 Vacation Rentals |
|---|---|
Lowest Price | $522 |
Highest Price | $574 |
Popular accommodation | Breathtaking views with an indoor private pool, come escape with us, Terra Alta - Incredible River Views and Hot Tub!, Charles Town Home w/ Private Pool & Hot Tub, Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor, The PINK PEARL in Historic Leesburg, Stunning House! Minutes From Shenandoah River, Cozy Country Getaway in the Heart of Upperville , Escape the city to this Spacious and Clean 5BR / 3.5BA home with a Heated Pool and Spa on 8 Acres in Horse & Wine Country, Charming 4-bedroom Estate - A Historic Gem in Clarke County, VA, Quaint Royal Cottage @ Historic Leesburg, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains |