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
Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun
Located in Purcellville, this vacation home is within a 5-minute drive of Fireman's Field and Purcellville Skating Rink.
Washer
Dryer
Pet-Friendly Berryville Home: Walk to Main Street!
With a stay at this vacation home in Berryville, you'll be a 5-minute walk from The Fire House Gallery and 5 minutes by foot from Barns of Rose Hill.
Kitchen
Washer
NEW LISTING! Mountain Chic Retreat by RedAwning
The price is $451 per night
$451
includes taxes & fees
$408 per night
Nov 24 - Nov 25
Free Cancellation
Located in Harpers Ferry, this vacation home is in the mountains, within a 15-minute drive of Shenandoah Lake Beach and Shenandoah River.
Kitchen
Air conditioning
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.
Pool
Hot Tub
Big Sunny Family House
With a stay at this vacation home, you'll be centrally located in Front Royal, within a 5-minute drive of Shenandoah National Park and Belle Boyd Cottage.
This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA.
Located in Winchester, this vacation home is in a rural location, a 4-minute drive from Appleland Sports Center and 6 minutes from The Kernstown Battlefield.
Kitchen
Washer
Mountain Getaway - 7 beds (2 King) - Large Common Area
Located in Harpers Ferry, this vacation home is in the mountains, a 5-minute drive from Shenandoah River and 6 minutes from Shenandoah Lake Beach.
Charles Town Townhome: 9 Mi to Harpers Ferry
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 Jefferson County Courthouse.
Terra Alta - Incredible River Views and Hot Tub!
The price is $457 per night
$457
includes taxes & fees
$413 per night
Dec 5 - Dec 6
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
Modern Country House on the Shenandoah River
When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.
Hot Tub, Poker Table, River Access & Kayaks and Wineries
The price is $414 per night
$414
includes taxes & fees
$372 per night
Dec 2 - Dec 3
When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.
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 | 201 Vacation Rentals |
---|---|
Lowest Price | $414 |
Highest Price | $457 |
Popular accommodation | Quiet Highland Home set on gorgeous rolling hills and farm in Western Loudoun, Pet-Friendly Berryville Home: Walk to Main Street!, NEW LISTING! Mountain Chic Retreat by RedAwning, Breathtaking views with an indoor private pool, come escape with us, Big Sunny Family House, This house is a 2 bedroom(s), 2 bathrooms, located in Winchester, VA., Mountain Getaway - 7 beds (2 King) - Large Common Area, Charles Town Townhome: 9 Mi to Harpers Ferry, Terra Alta - Incredible River Views and Hot Tub!, Modern Country House on the Shenandoah River , Hot Tub, Poker Table, River Access & Kayaks and Wineries, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor |