Upperville Vacation Rentals
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Distance from
5 mi
50 rentals in Upperville.
The Mill House in Upperville -
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Historic house in Upperville! Wineries, equestrian events, great location!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
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The following properties within 20 miles of Upperville match all your filters:
Blue Mountain Log Cabin
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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'Anny's Farm House' in Round Hill Wine Country!
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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Middleburg - Charming Cottage - 5 min to center of M'burg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Virginia Wine Country Retreat 60 mi. from DC
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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"Best Value": WATERFRONT! 5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester
Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
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ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room
Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall
Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
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House in Virginia’s Horse and Wine Country
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Historic Mountain Cottage at Blue Ridge Overlook
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
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Appalachian Estates Cabin
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Peaceful Hideaway w/ Shenandoah River Access
Rental Home
1 bedroom
1 bathroom
Sleeps 7
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Bedrooms 2, Bathrooms 1, Sleeps 4
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Historical cottage in the town of Paris
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
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5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Cottage near Middleburg in the Center of Hunt and Wine Country
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country
Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
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Beavers Hill Cottage mountain and wine country getaway
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Private entrance Guest suite in Magnificent Manor: stunning views on 150 acres.
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths
Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
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Stone Cottage, Comfort, Peace and Nature
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Lovely Guest House 2.5 miles from downtown Middleburg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Private, Independent Apartment on Magnificent Manor
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
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Cozy and secluded cottage located in the heart of horse country.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
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Historic Farmhouse Suite in Virginia Hunt & Wine Country
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
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Whole house near Middleburg in Piedmont horse country
Rental Home
7 bedrooms
7 bathrooms
Sleeps 14
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Beautifully Restored Log Cabin in Bluemont, VA
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Modern Home on Middleburg Equestrian Farm
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Historic Equestrian Estate in Middleburg Hunt Country
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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Wine Country Mountain Retreat
Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
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Design home near Middleburg VA available for seasonal stays
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Large Modern House, Wine Country, Delaplane, VA
Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
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*New* Sampson's Lodge: Mountain Views & Hot Tub
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
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Stunning Bluemont Manor with 8 Bedrooms 7 Baths
Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
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18th Century Stone Cottage minutes from historic Middleburg
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres
Rental Home
7 bedrooms
7 bathrooms
Sleeps 18
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Bluemont Belle is settled on a Historic Equestrian VA Estate
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
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Hidden View
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Historic 1740 log home in the village of Unison, Virginia.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Bright Bluemont Home w/ On-Site Pond & Mtn Views!
Rental Home
5 bedrooms
5 bathrooms
Sleeps 5
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Old Historic Charm on a Lovely 66 acre Farm
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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Farm Charm with City Style
Rental Home
1 bedroom
1 bathroom
Sleeps 2
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It's Own Destination / Farm Cottage with Mountain Views & Pond
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Showing results 1-50 of 50
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!
- Middleburg - Charming Cottage - 5 min to center of M'burg
- 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!
- Middleburg - Charming Cottage - 5 min to center of M'burg
- 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!
- Appalachian Estates Cabin