Upperville Guest Houses
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
Guest Houses in Upperville
Briar Patch Bed & Breakfast Inn
23130 Briar Patch Ln Middleburg VA
$275 nightly
The price is $314 total per night
$314 total
Dec 8 - Dec 9
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
Located in Middleburg, Briar Patch Bed & Breakfast Inn is within a 5-minute drive of Cana Vineyards and Winery and Aldie Mill Historic Park.
Pool
Hot Tub
Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment
The Plains VA
$403 nightly
The price is $432 total per night
$432 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in Marshall, this guesthouse is on a lake, within a 15-minute drive of Great Meadow and Marshall Center.
Free WiFi
Air conditioning
Guest House at Mt Independence
Delaplane VA
Located in Delaplane, this guesthouse is in the mountains, a 2-minute drive from Delaplane Cellars and 7 minutes from Sky Meadows State Park.
Pet friendly
Free WiFi
Riverfront Oasis with Mountain Views, close to town
Middletown VA
With a stay at this guesthouse in Middletown, you'll be on the waterfront, within a 15-minute drive of Shenandoah National Park and Shenandoah River.
Free WiFi
Air conditioning
Guest House at Mt. Independence
2254 Winchester Rd Delaplane VA
Located in Delaplane, Guest House at Mt. Independence is in the mountains, a 2-minute drive from Delaplane Cellars and 7 minutes from Sky Meadows State Park.
Spa
Pet friendly
Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed
Winchester VA
Located in Winchester, this guesthouse is within a 5-minute drive of Abrams Creek Wetlands Preserve and Shenandoah University.
Air conditioning
Parking available
Secret Gardens Carriage House
Winchester VA
Located in Winchester, this guesthouse is within a 5-minute drive of The Kernstown Battlefield and Shenandoah University.
Air conditioning
Parking available
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 Guest Houses essential information
Accommodation | 10 Guest Houses |
|---|---|
Lowest Price | $314 |
Highest Price | $432 |
Popular accommodation | Briar Patch Bed & Breakfast Inn, Magical Unicorn Hollow /Wineries /Great Meadows Events Fully furnished apartment, Guest House at Mt Independence, Riverfront Oasis with Mountain Views, close to town , Guest House at Mt. Independence, Peaceful Secret Gardens Tiny Home - loft & stairs lead to a Queen Size Bed, Secret Gardens Carriage House, Weddings at Highholdborne, Chilton House Suites |