Upperville Vacation Rentals
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49 rentals in Upperville.
The Mill House in Upperville -
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Historic house in Upperville! Wineries, equestrian events, great location!
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Hunt Country cottage in Upperville!
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Cozy Country Getaway in the Heart of Upperville
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Historic spacious home in the heart of Upperville, VA
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Private, comfortable 4-bedroom/3 bath cottage in Upperville with full amenities
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The following properties within 20 miles of Upperville match all your filters:
Beautifully Restored Log Cabin in Bluemont, VA
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Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Capstone!
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Historical cottage in the town of Paris
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18th Century Stone Cottage minutes from historic Middleburg
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Beavers Hill Cottage a Mountain getaway in Virginia Wine country!
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Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country
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Pets? YES! � Hot Tub ★ Gym ★ Firepit ★ Game Room ★ Path to Winery
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Whitetail Summit - Shenandoah/hot tub/wineries
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1800s Family Farmhouse with Huge Yard- PRIVATE TRAIL WALK TO WINE!
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Middleburg - Charming Cottage - 5 min to center of M'burg
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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
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Virginia Wine Country Retreat 60 mi. from DC
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Lovely Guest House 2.5 miles from downtown Middleburg
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House in Virginia’s Horse and Wine Country
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Bright Bluemont Home w/ On-Site Pond & Mtn Views!
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Cozy and secluded cottage located in the heart of horse country.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries
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Bedrooms 2, Bathrooms 1, Sleeps 4
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Hidden View
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Romantic, family friendly mountain getaway w hot tub near wineries & skyline
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Historic 1740 log home in the village of Unison, Virginia.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi
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Historic Mountain Cottage at Blue Ridge Overlook
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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'Anny's Farm House' in Round Hill Wine Country!
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Blue Mountain Log Cabin
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Modern Home on Middleburg Equestrian Farm
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
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Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Bluemont Belle is settled on a Historic Equestrian VA Estate
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Historic home with 7 BR near Middleburg, VA in Piedmont horse country
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Stunning Bluemont Manor with 9 Bedrooms 7 Baths
Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
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Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
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Serene Farmhouse and former winery on 44 acres of rolling hills.
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Guest House at Mt Independence
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Paris Manor w/ Private Pool!
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Historic home nestled in the heart of horse and wine country. Kids/pet
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Blue Mountain Log Cabin with Hot Tub, Fireplace, Shenandoah Valley Views, & More
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Winemakers Cottage at Barrel Oak Winery & Brewery
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private apartment on a beautiful private farm!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historical Paris Cabin on Farm w/ Fire Pit!
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Showing results 1-49 of 49
Frequently Asked Questions about Upperville
- Yes, here are some popular vacation rentals in Upperville that have a pool:
- The Mill House in Upperville -
- Historic house in Upperville! Wineries, equestrian events, great location!
- Hunt Country cottage in Upperville!
- Yes, here are some popular vacation rentals in Upperville that have internet access:
- The Mill House in Upperville -
- Historic house in Upperville! Wineries, equestrian events, great location!
- Hunt Country cottage in Upperville!
- Some of the most popular kid friendly rentals in Upperville are:
- The Mill House in Upperville -
- Historic house in Upperville! Wineries, equestrian events, great location!
- Hunt Country cottage in Upperville!
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