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Holiday Rentals in Upperville

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5 km
50 rentals in Upperville.
The Mill House in Upperville -, holiday rental in Upperville
The Mill House in Upperville -, holiday rental in Upperville
The Mill House in Upperville -, holiday rental in Upperville

The Mill House in Upperville -

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic house in Upperville!  Wineries, equestrian events, great location!, holiday rental in Upperville
Historic house in Upperville!  Wineries, equestrian events, great location!, holiday rental in Upperville
Historic house in Upperville!  Wineries, equestrian events, great location!, holiday rental in Upperville

Historic house in Upperville! Wineries, equestrian events, great location!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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The following properties within 32 kms of Upperville match all your filters:
Beautifully Restored Log Cabin in Bluemont, VA, holiday rental in Upperville
Beautifully Restored Log Cabin in Bluemont, VA, holiday rental in Upperville
Beautifully Restored Log Cabin in Bluemont, VA, holiday rental in Upperville

Beautifully Restored Log Cabin in Bluemont, VA

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Whiskey Hill Cabin a mountain getaway in Virginia wine country!, holiday rental in Upperville
Whiskey Hill Cabin a mountain getaway in Virginia wine country!, holiday rental in Upperville
Whiskey Hill Cabin a mountain getaway in Virginia wine country!, holiday rental in Upperville

Whiskey Hill Cabin a mountain getaway in Virginia wine country!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Front Royal Hilltop Cabin w/ Panoramic Views!, holiday rental in Upperville
Front Royal Hilltop Cabin w/ Panoramic Views!, holiday rental in Upperville
Front Royal Hilltop Cabin w/ Panoramic Views!, holiday rental in Upperville

Front Royal Hilltop Cabin w/ Panoramic Views!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historical cottage in the town of Paris!, holiday rental in Upperville
Historical cottage in the town of Paris!, holiday rental in Upperville
Historical cottage in the town of Paris!, holiday rental in Upperville

Historical cottage in the town of Paris!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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18th Century Stone Cottage minutes from historic Middleburg, holiday rental in Upperville
18th Century Stone Cottage minutes from historic Middleburg, holiday rental in Upperville
18th Century Stone Cottage minutes from historic Middleburg, holiday rental in Upperville

18th Century Stone Cottage minutes from historic Middleburg

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beavers Hill Cottage mountain and wine country getaway, holiday rental in Upperville
Beavers Hill Cottage mountain and wine country getaway, holiday rental in Upperville
Beavers Hill Cottage mountain and wine country getaway, holiday rental in Upperville

Beavers Hill Cottage mountain and wine country getaway

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, holiday rental in Upperville
Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, holiday rental in Upperville
Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, holiday rental in Upperville

Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Wine Country Mountain Retreat, holiday rental in Upperville
Wine Country Mountain Retreat, holiday rental in Upperville
Wine Country Mountain Retreat, holiday rental in Upperville

Wine Country Mountain Retreat

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Hideaway w/ Shenandoah River Access, holiday rental in Upperville
Peaceful Hideaway w/ Shenandoah River Access, holiday rental in Upperville
Peaceful Hideaway w/ Shenandoah River Access, holiday rental in Upperville

Peaceful Hideaway w/ Shenandoah River Access

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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One. Minute. To. Wine. Heaven. ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, holiday rental in Upperville
One. Minute. To. Wine. Heaven. ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, holiday rental in Upperville
One. Minute. To. Wine. Heaven. ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, holiday rental in Upperville

One. Minute. To. Wine. Heaven. ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Whitetail Summit - Shenandoah/hot tub/wineries, holiday rental in Upperville
Whitetail Summit - Shenandoah/hot tub/wineries, holiday rental in Upperville
Whitetail Summit - Shenandoah/hot tub/wineries, holiday rental in Upperville

Whitetail Summit - Shenandoah/hot tub/wineries

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, holiday rental in Upperville
1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, holiday rental in Upperville
1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, holiday rental in Upperville

1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Middleburg - Charming Cottage - 5 min to center of M'burg, holiday rental in Upperville
Middleburg - Charming Cottage - 5 min to center of M'burg, holiday rental in Upperville
Middleburg - Charming Cottage - 5 min to center of M'burg, holiday rental in Upperville

Middleburg - Charming Cottage - 5 min to center of M'burg

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, holiday rental in Upperville
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, holiday rental in Upperville
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, holiday rental in Upperville

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Upperville
Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Upperville
Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Upperville

Virginia Wine Country Retreat 60 mi. from DC

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, holiday rental in Upperville
New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, holiday rental in Upperville
New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, holiday rental in Upperville

New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lovely Guest House 2.5 miles from downtown Middleburg, holiday rental in Upperville
Lovely Guest House 2.5 miles from downtown Middleburg, holiday rental in Upperville
Lovely Guest House 2.5 miles from downtown Middleburg, holiday rental in Upperville

Lovely Guest House 2.5 miles from downtown Middleburg

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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House in Virginia’s Horse and Wine Country, holiday rental in Upperville
House in Virginia’s Horse and Wine Country, holiday rental in Upperville
House in Virginia’s Horse and Wine Country, holiday rental in Upperville

House in Virginia’s Horse and Wine Country

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bright Bluemont Home w/ On-Site Pond & Mtn Views!, holiday rental in Upperville
Bright Bluemont Home w/ On-Site Pond & Mtn Views!, holiday rental in Upperville
Bright Bluemont Home w/ On-Site Pond & Mtn Views!, holiday rental in Upperville

Bright Bluemont Home w/ On-Site Pond & Mtn Views!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., holiday rental in Upperville
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., holiday rental in Upperville
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., holiday rental in Upperville

5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy and secluded cottage located in the heart of horse country., holiday rental in Upperville
Cozy and secluded cottage located in the heart of horse country., holiday rental in Upperville
Cozy and secluded cottage located in the heart of horse country., holiday rental in Upperville

Cozy and secluded cottage located in the heart of horse country.

Holiday Rental House
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, holiday rental in Upperville
Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS, holiday rental in Upperville
Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS, holiday rental in Upperville

Romantic Shabby Chic Cottage on 5 acre property near wineries and Blue Ridge MTS

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Upperville
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Upperville
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Upperville

Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville

Bedrooms 2, Bathrooms 1, Sleeps 4

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Farmhouse Suite in Virginia Hunt & Wine Country, holiday rental in Upperville
Historic Farmhouse Suite in Virginia Hunt & Wine Country, holiday rental in Upperville
Historic Farmhouse Suite in Virginia Hunt & Wine Country, holiday rental in Upperville

Historic Farmhouse Suite in Virginia Hunt & Wine Country

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Hidden View, holiday rental in Upperville
Hidden View, holiday rental in Upperville
Hidden View, holiday rental in Upperville

Hidden View

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private, Independent Apartment on Magnificent Manor, holiday rental in Upperville
Private, Independent Apartment on Magnificent Manor, holiday rental in Upperville
Private, Independent Apartment on Magnificent Manor, holiday rental in Upperville

Private, Independent Apartment on Magnificent Manor

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage near Middleburg in the Center of Hunt and Wine Country, holiday rental in Upperville
Cottage near Middleburg in the Center of Hunt and Wine Country, holiday rental in Upperville
Cottage near Middleburg in the Center of Hunt and Wine Country, holiday rental in Upperville

Cottage near Middleburg in the Center of Hunt and Wine Country

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, holiday rental in Upperville

Bedrooms 2, Bathrooms 1, Sleeps 4

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bedrooms 3, Bathrooms 1, Sleeps 6, holiday rental in Upperville
Bedrooms 3, Bathrooms 1, Sleeps 6, holiday rental in Upperville
Bedrooms 3, Bathrooms 1, Sleeps 6, holiday rental in Upperville

Bedrooms 3, Bathrooms 1, Sleeps 6

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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It's Own Destination / Farm Cottage with Mountain Views & Pond, holiday rental in Upperville
It's Own Destination / Farm Cottage with Mountain Views & Pond, holiday rental in Upperville
It's Own Destination / Farm Cottage with Mountain Views & Pond, holiday rental in Upperville

It's Own Destination / Farm Cottage with Mountain Views & Pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, holiday rental in Upperville
Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, holiday rental in Upperville
Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, holiday rental in Upperville

Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic 1740 log home in the village of Unison, Virginia., holiday rental in Upperville
Historic 1740 log home in the village of Unison, Virginia., holiday rental in Upperville
Historic 1740 log home in the village of Unison, Virginia., holiday rental in Upperville

Historic 1740 log home in the village of Unison, Virginia.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi, holiday rental in Upperville
♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi, holiday rental in Upperville
♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi, holiday rental in Upperville

♛Royal A-Frame♛HOT TUB★PetsOK★WoodStove★FASTwifi

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Upperville
Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Upperville
Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Upperville

Historic Mountain Cottage at Blue Ridge Overlook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Upperville
'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Upperville
'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Upperville

'Anny's Farm House' in Round Hill Wine Country!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blue Mountain Log Cabin, holiday rental in Upperville
Blue Mountain Log Cabin, holiday rental in Upperville
Blue Mountain Log Cabin, holiday rental in Upperville

Blue Mountain Log Cabin

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern Home on Middleburg Equestrian Farm, holiday rental in Upperville
Modern Home on Middleburg Equestrian Farm, holiday rental in Upperville
Modern Home on Middleburg Equestrian Farm, holiday rental in Upperville

Modern Home on Middleburg Equestrian Farm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, holiday rental in Upperville
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, holiday rental in Upperville
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, holiday rental in Upperville

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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"Best Value": WATERFRONT!  5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester, holiday rental in Upperville
"Best Value": WATERFRONT!  5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester, holiday rental in Upperville
"Best Value": WATERFRONT!  5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester, holiday rental in Upperville

"Best Value": WATERFRONT! 5-Star-Rated & VIEWS Bluemont/Middleburg/Winchester

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Bedrooms 4, Bathrooms 2, Sleeps 8, holiday rental in Upperville
Bedrooms 4, Bathrooms 2, Sleeps 8, holiday rental in Upperville
Bedrooms 4, Bathrooms 2, Sleeps 8, holiday rental in Upperville

Bedrooms 4, Bathrooms 2, Sleeps 8

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, holiday rental in Upperville
Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, holiday rental in Upperville
Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, holiday rental in Upperville

Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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**New**: The Bluemont Belle is settled on a Historic Equestrian VA Estate, holiday rental in Upperville
**New**: The Bluemont Belle is settled on a Historic Equestrian VA Estate, holiday rental in Upperville
**New**: The Bluemont Belle is settled on a Historic Equestrian VA Estate, holiday rental in Upperville

**New**: The Bluemont Belle is settled on a Historic Equestrian VA Estate

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Historic Equestrian Estate in Middleburg Hunt Country, holiday rental in Upperville
Historic Equestrian Estate in Middleburg Hunt Country, holiday rental in Upperville
Historic Equestrian Estate in Middleburg Hunt Country, holiday rental in Upperville

Historic Equestrian Estate in Middleburg Hunt Country

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Whole house near Middleburg in Piedmont horse country, holiday rental in Upperville
Whole house near Middleburg in Piedmont horse country, holiday rental in Upperville
Whole house near Middleburg in Piedmont horse country, holiday rental in Upperville

Whole house near Middleburg in Piedmont horse country

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, holiday rental in Upperville
**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, holiday rental in Upperville
**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, holiday rental in Upperville

**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Stunning Bluemont Manor with 8 Bedrooms 7 Baths, holiday rental in Upperville
Stunning Bluemont Manor with 8 Bedrooms 7 Baths, holiday rental in Upperville
Stunning Bluemont Manor with 8 Bedrooms 7 Baths, holiday rental in Upperville

Stunning Bluemont Manor with 8 Bedrooms 7 Baths

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Upperville
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Upperville
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Upperville

Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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