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Upperville Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Upperville.
The Mill House in Upperville -, vacation rental in Upperville
The Mill House in Upperville -, vacation rental in Upperville
The Mill House in Upperville -, vacation rental in Upperville

The Mill House in Upperville -

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

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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The following properties within 20 miles of Upperville match all your filters:
Blue Mountain Log Cabin, vacation rental in Upperville
Blue Mountain Log Cabin, vacation rental in Upperville
Blue Mountain Log Cabin, vacation rental in Upperville

Blue Mountain Log Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Upperville
'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Upperville
'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Upperville

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Middleburg - Charming Cottage - 5 min to center of M'burg, vacation rental in Upperville
Middleburg - Charming Cottage - 5 min to center of M'burg, vacation rental in Upperville
Middleburg - Charming Cottage - 5 min to center of M'burg, vacation rental in Upperville

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Virginia Wine Country Retreat 60 mi. from DC, vacation rental in Upperville
Virginia Wine Country Retreat 60 mi. from DC, vacation rental in Upperville
Virginia Wine Country Retreat 60 mi. from DC, vacation rental in Upperville

Virginia Wine Country Retreat 60 mi. from DC

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, vacation rental in Upperville
Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, vacation rental in Upperville
Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country, vacation rental in Upperville

Beautiful Estate Nestled in the Blueridge Near Bluemont Wine Country

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, vacation rental in Upperville
ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, vacation rental in Upperville
ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room, vacation rental in Upperville

ONE MINUTE TO WINE HEAVEN ❤️ Hot tub ★ Home gym ★ Fire pit ★ Game Room

Rental Home
5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, vacation rental in Upperville
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, vacation rental in Upperville
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, vacation rental in Upperville

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

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Upperville
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Upperville
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Upperville

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

Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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House in Virginia’s Horse and Wine Country, vacation rental in Upperville
House in Virginia’s Horse and Wine Country, vacation rental in Upperville
House in Virginia’s Horse and Wine Country, vacation rental in Upperville

House in Virginia’s Horse and Wine Country

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, vacation rental in Upperville
1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, vacation rental in Upperville
1840 7-Acre Farmhouse in VA Wine & Horse Country- Hot Tub, Patio Fire Place, vacation rental in Upperville

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Upperville
Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Upperville
Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Upperville

Historic Mountain Cottage at Blue Ridge Overlook

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Appalachian Estates Cabin, vacation rental in Upperville
Appalachian Estates Cabin, vacation rental in Upperville
Appalachian Estates Cabin, vacation rental in Upperville

Appalachian Estates Cabin

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Upperville
Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Upperville
Peaceful Hideaway w/ Shenandoah River Access, vacation rental in Upperville

Peaceful Hideaway w/ Shenandoah River Access

Rental Home
1 bedroom
1 bathroom
Sleeps 7
Match: Sleeps
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Bedrooms 2, Bathrooms 1, Sleeps 4, vacation rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, vacation rental in Upperville
Bedrooms 2, Bathrooms 1, Sleeps 4, vacation rental in Upperville

Bedrooms 2, Bathrooms 1, Sleeps 4

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historical cottage in the town of Paris, vacation rental in Upperville
Historical cottage in the town of Paris, vacation rental in Upperville
Historical cottage in the town of Paris, vacation rental in Upperville

Historical cottage in the town of Paris

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Upperville
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Upperville
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More, vacation rental in Upperville

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., vacation rental in Upperville
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., vacation rental in Upperville
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath., vacation rental in Upperville

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

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

Cottage near Middleburg in the Center of Hunt and Wine Country

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country, vacation rental in Upperville
Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country, vacation rental in Upperville
Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country, vacation rental in Upperville

Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

Rental Home
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Beavers Hill Cottage mountain and wine country getaway, vacation rental in Upperville
Beavers Hill Cottage mountain and wine country getaway, vacation rental in Upperville
Beavers Hill Cottage mountain and wine country getaway, vacation rental in Upperville

Beavers Hill Cottage mountain and wine country getaway

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private entrance Guest suite in Magnificent Manor:  stunning views on 150 acres., vacation rental in Upperville
Private entrance Guest suite in Magnificent Manor:  stunning views on 150 acres., vacation rental in Upperville
Private entrance Guest suite in Magnificent Manor:  stunning views on 150 acres., vacation rental in Upperville

Private entrance Guest suite in Magnificent Manor: stunning views on 150 acres.

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, vacation rental in Upperville
Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, vacation rental in Upperville
Romantic "Cabin in the Clouds" mountain getaway near vineyards & Skyline Drive, vacation rental in Upperville

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, vacation rental in Upperville
Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, vacation rental in Upperville
Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths, vacation rental in Upperville

Magnificent Bluemont Lodge with 5 Bedrooms 3 Baths

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Stone Cottage, Comfort, Peace and Nature, vacation rental in Upperville
Stone Cottage, Comfort, Peace and Nature, vacation rental in Upperville
Stone Cottage, Comfort, Peace and Nature, vacation rental in Upperville

Stone Cottage, Comfort, Peace and Nature

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Guest House 2.5 miles from downtown Middleburg, vacation rental in Upperville
Lovely Guest House 2.5 miles from downtown Middleburg, vacation rental in Upperville
Lovely Guest House 2.5 miles from downtown Middleburg, vacation rental in Upperville

Lovely Guest House 2.5 miles from downtown Middleburg

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private, Independent Apartment on Magnificent Manor, vacation rental in Upperville
Private, Independent Apartment on Magnificent Manor, vacation rental in Upperville
Private, Independent Apartment on Magnificent Manor, vacation rental in Upperville

Private, Independent Apartment on Magnificent Manor

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Cozy and secluded cottage located in the heart of horse country., vacation rental in Upperville
Cozy and secluded cottage located in the heart of horse country., vacation rental in Upperville
Cozy and secluded cottage located in the heart of horse country., vacation rental in Upperville

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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Historic Farmhouse Suite in Virginia Hunt & Wine Country, vacation rental in Upperville
Historic Farmhouse Suite in Virginia Hunt & Wine Country, vacation rental in Upperville
Historic Farmhouse Suite in Virginia Hunt & Wine Country, vacation rental in Upperville

Historic Farmhouse Suite in Virginia Hunt & Wine Country

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, vacation rental in Upperville
New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, vacation rental in Upperville
New Renovations 4 Blue Ridge Mountain Cedar Log Cabin's breathtaking VIEW!, vacation rental in Upperville

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Whole house near Middleburg in Piedmont horse country, vacation rental in Upperville
Whole house near Middleburg in Piedmont horse country, vacation rental in Upperville
Whole house near Middleburg in Piedmont horse country, vacation rental in Upperville

Whole house near Middleburg in Piedmont horse country

Rental Home
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
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Beautifully Restored Log Cabin in Bluemont, VA, vacation rental in Upperville
Beautifully Restored Log Cabin in Bluemont, VA, vacation rental in Upperville
Beautifully Restored Log Cabin in Bluemont, VA, vacation rental in Upperville

Beautifully Restored Log Cabin in Bluemont, VA

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Home on Middleburg Equestrian Farm, vacation rental in Upperville
Modern Home on Middleburg Equestrian Farm, vacation rental in Upperville
Modern Home on Middleburg Equestrian Farm, vacation rental in Upperville

Modern Home on Middleburg Equestrian Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Equestrian Estate in Middleburg Hunt Country, vacation rental in Upperville
Historic Equestrian Estate in Middleburg Hunt Country, vacation rental in Upperville
Historic Equestrian Estate in Middleburg Hunt Country, vacation rental in Upperville

Historic Equestrian Estate in Middleburg Hunt Country

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Wine Country Mountain Retreat, vacation rental in Upperville
Wine Country Mountain Retreat, vacation rental in Upperville
Wine Country Mountain Retreat, vacation rental in Upperville

Wine Country Mountain Retreat

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Design home near Middleburg VA available for seasonal stays, vacation rental in Upperville
Design home near Middleburg VA available for seasonal stays, vacation rental in Upperville
Design home near Middleburg VA available for seasonal stays, vacation rental in Upperville

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, vacation rental in Upperville
Large Modern House, Wine Country, Delaplane, VA, vacation rental in Upperville
Large Modern House, Wine Country, Delaplane, VA, vacation rental in Upperville

Large Modern House, Wine Country, Delaplane, VA

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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*New* Sampson's Lodge: Mountain Views & Hot Tub, vacation rental in Upperville
*New* Sampson's Lodge: Mountain Views & Hot Tub, vacation rental in Upperville
*New* Sampson's Lodge: Mountain Views & Hot Tub, vacation rental in Upperville

*New* Sampson's Lodge: Mountain Views & Hot Tub

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Stunning Bluemont Manor with 8 Bedrooms 7 Baths, vacation rental in Upperville
Stunning Bluemont Manor with 8 Bedrooms 7 Baths, vacation rental in Upperville
Stunning Bluemont Manor with 8 Bedrooms 7 Baths, vacation rental in Upperville

Stunning Bluemont Manor with 8 Bedrooms 7 Baths

Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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18th Century Stone Cottage minutes from historic Middleburg, vacation rental in Upperville
18th Century Stone Cottage minutes from historic Middleburg, vacation rental in Upperville
18th Century Stone Cottage minutes from historic Middleburg, vacation rental in Upperville

18th Century Stone Cottage minutes from historic Middleburg

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, vacation rental in Upperville
**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, vacation rental in Upperville
**New**: Blue Ridge MTN Top Estate Retreat w/ 97 Acres, vacation rental in Upperville

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

Rental Home
7 bedrooms
7 bathrooms
Sleeps 18
Match: Sleeps
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Bluemont Belle is settled on a Historic Equestrian VA Estate, vacation rental in Upperville
Bluemont Belle is settled on a Historic Equestrian VA Estate, vacation rental in Upperville
Bluemont Belle is settled on a Historic Equestrian VA Estate, vacation rental in Upperville

Bluemont Belle is settled on a Historic Equestrian VA Estate

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
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Hidden View, vacation rental in Upperville
Hidden View, vacation rental in Upperville
Hidden View, vacation rental in Upperville

Hidden View

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bright Bluemont Home w/ On-Site Pond & Mtn Views!, vacation rental in Upperville
Bright Bluemont Home w/ On-Site Pond & Mtn Views!, vacation rental in Upperville
Bright Bluemont Home w/ On-Site Pond & Mtn Views!, vacation rental in Upperville

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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Old Historic Charm on a Lovely 66 acre Farm, vacation rental in Upperville
Old Historic Charm on a Lovely 66 acre Farm, vacation rental in Upperville
Old Historic Charm on a Lovely 66 acre Farm, vacation rental in Upperville

Old Historic Charm on a Lovely 66 acre Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Farm Charm with City Style, vacation rental in Upperville
Farm Charm with City Style, vacation rental in Upperville
Farm Charm with City Style, vacation rental in Upperville

Farm Charm with City Style

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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It's Own Destination / Farm Cottage with Mountain Views & Pond, vacation rental in Upperville
It's Own Destination / Farm Cottage with Mountain Views & Pond, vacation rental in Upperville
It's Own Destination / Farm Cottage with Mountain Views & Pond, vacation rental in Upperville

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Upperville