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Upperville Holiday Rentals

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50 rentals in Upperville.
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The Mill House in Upperville - Cozy  fireplace, outside bonfire - fall is here!, holiday rental in Upperville

The Mill House in Upperville - Cozy fireplace, outside bonfire - fall is here!

4 bedrooms
3 bathrooms
Sleeps 8
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Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Upperville

Historic Manor House on Shenandoah River in Virginia's Wine Country

5 bedrooms
4 bathrooms
Sleeps 14
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A Restored Wagon Barn On A 1790's Farm, holiday rental in Upperville

A Restored Wagon Barn On A 1790's Farm

1 bedroom
1 bathroom
Sleeps 4
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Middleburg, VA - Private Cottage, Sophisticated Country Charm  - Newly Remodeled, holiday rental in Upperville

Middleburg, VA - Private Cottage, Sophisticated Country Charm - Newly Remodeled

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Historic and Updated Farmhouse Built in 1808, holiday rental in Upperville

Historic and Updated Farmhouse Built in 1808

2 bedrooms
1 bathroom
Sleeps 6
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Blue Mountain Log Cabin, holiday rental in Upperville

Blue Mountain Log Cabin

3 bedrooms
2 bathrooms
Sleeps 5
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The Countryside Home, holiday rental in Upperville

The Countryside Home

4 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, holiday rental in Upperville

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

3 bedrooms
4 bathrooms
Sleeps 9
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Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor, holiday rental in Upperville

Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Upperville

Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated

6 bedrooms
3 bathrooms
Sleeps 14
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Gorgeous English Hunt Country Cottage, holiday rental in Upperville

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking views  with an  indoor private pool, come escape with us, holiday rental in Upperville

Breathtaking views with an indoor private pool, come escape with us

6 bedrooms
5 bathrooms
Sleeps 16
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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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Weekend getaway short distance from DC/Northern Virginia, holiday rental in Upperville

Weekend getaway short distance from DC/Northern Virginia

1 bedroom
1 bathroom
Sleeps 4
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Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., holiday rental in Upperville

Perfect Hunt Box in Clarke Co. Minutes to Upperville and Middleburg.

2 bedrooms
3 bathrooms
Sleeps 4
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Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres, holiday rental in Upperville

Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres

3 bedrooms
2 bathrooms
Sleeps 8
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Alpacas & The Stars at night. Private Retreat. Fun & Peace, holiday rental in Upperville

Alpacas & The Stars at night. Private Retreat. Fun & Peace

3 bedrooms
1 bathroom
Sleeps 6
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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Upperville

Virginia Wine Country Retreat 60 mi. from DC

4 bedrooms
4 bathrooms
Sleeps 10
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Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi  ***ASK FOR NEW YEAR'S QUOTE***, holiday rental in Upperville

Leesburg Ashburn 26-acre Farm IAD/12mi Wine/11mi ***ASK FOR NEW YEAR'S QUOTE***

4 bedrooms
3 bathrooms
Sleeps 16
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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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Meadowbrook -Entire House - Close to Vineyards and Breweries, holiday rental in Upperville

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
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

7 bedrooms
8 bathrooms
Sleeps 16
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Paradise in Horse Country, holiday rental in Upperville

Paradise in Horse Country

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Upperville

Historic Mountain Cottage at Blue Ridge Overlook

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country, holiday rental in Upperville

Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Cabin Hidden Away on a Lake!, holiday rental in Upperville

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, holiday rental in Upperville

The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use

3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Dome Of Your Dreams!, holiday rental in Upperville

Dome Of Your Dreams!

2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Shannondale Lake House, holiday rental in Upperville

Shannondale Lake House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Apt in Harpers Ferry by the lake!, holiday rental in Upperville

Cozy Apt in Harpers Ferry by the lake!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Love Cottage in Harpers Ferry by the lake!, holiday rental in Upperville

The Love Cottage in Harpers Ferry by the lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Idle Hour at Chester Gap, holiday rental in Upperville

Idle Hour at Chester Gap

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va), holiday rental in Upperville

3 BR Chalet 60 Mi. West of Washington (Linden/Front Royal Va)

3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Upperville

Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The Blueridge Cabin!, holiday rental in Upperville

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Vista Magnifique - private mountaintop estate w/ beautiful views of wine country, holiday rental in Upperville

Vista Magnifique - private mountaintop estate w/ beautiful views of wine country

3 bedrooms
3 bathrooms
Sleeps 6
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!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Travelers Rest in Harpers Ferry by the lake, holiday rental in Upperville

The Travelers Rest in Harpers Ferry by the lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Virginia Wine Country Villa w/Pool & Yard, holiday rental in Upperville

Historic Virginia Wine Country Villa w/Pool & Yard

6 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
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Pet-Friendly Home in Heart of Wine Country!, holiday rental in Upperville

Pet-Friendly Home in Heart of Wine Country!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Outpost Suite 2- A Curated Farmhouse Suite, holiday rental in Upperville

The Outpost Suite 2- A Curated Farmhouse Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Outpost Whimsical Farmhouse Retreat +Tesla Charger, holiday rental in Upperville

The Outpost Whimsical Farmhouse Retreat +Tesla Charger

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit, holiday rental in Upperville

NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Peaceful Escape near Shenandoah National Park, holiday rental in Upperville

NEW! Peaceful Escape near Shenandoah National Park

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Family Retreat w/ Deck Near Appalachian Trail, holiday rental in Upperville

NEW! Family Retreat w/ Deck Near Appalachian Trail

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cottage w 2 Private Lakes & River Access, Fire Pit, holiday rental in Upperville

Cottage w 2 Private Lakes & River Access, Fire Pit

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!, holiday rental in Upperville

Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEW! Lakefront Home w/ Canoe, 7 Mi to Front Royal!, holiday rental in Upperville

NEW! Lakefront Home w/ Canoe, 7 Mi to Front Royal!

1 bedroom
3 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Updated Front Royal Home on Shenandoah River!, holiday rental in Upperville

NEW! Updated Front Royal Home on Shenandoah River!

1 bedroom
4 bathrooms
Sleeps 9
Match: Sleeps
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NEW Rare 'Cabin in the Clouds' Mountain Getaway w/ Hot Tub City and valley views, holiday rental in Upperville

NEW Rare 'Cabin in the Clouds' Mountain Getaway w/ Hot Tub City and valley views

2 bedrooms
2 bathrooms
Sleeps 6
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