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Middleburg Holiday Rentals

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50 rentals in Middleburg.
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Middleburg, VA - Private Cottage, Sophisticated Country Charm  - Newly Remodeled, holiday rental in Middleburg

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

2 bedrooms
2 bathrooms
Sleeps 4
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Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor, holiday rental in Middleburg

Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor

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

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 Middleburg

A Restored Wagon Barn On A 1790's Farm

1 bedroom
1 bathroom
Sleeps 4
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The Mill House in Upperville - Cozy  fireplace, outside bonfire - fall is here!, holiday rental in Middleburg

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

4 bedrooms
3 bathrooms
Sleeps 8
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Historic and Updated Farmhouse Built in 1808, holiday rental in Middleburg

Historic and Updated Farmhouse Built in 1808

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

Blue Mountain Log Cabin

3 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, holiday rental in Middleburg

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

3 bedrooms
4 bathrooms
Sleeps 9
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Escape the city & work, home school from the country!, holiday rental in Middleburg

Escape the city & work, home school from the country!

4 bedrooms
3 bathrooms
Sleeps 10
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Hidden Hollow Farm - Pool; Game Rm; Vineyards; 45 min. to DC, Riverwalk & Trails, holiday rental in Middleburg

Hidden Hollow Farm - Pool; Game Rm; Vineyards; 45 min. to DC, Riverwalk & Trails

7 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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The Countryside Home, holiday rental in Middleburg

The Countryside Home

4 bedrooms
3 bathrooms
Sleeps 8
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Breathtaking views  with an  indoor private pool, come escape with us, holiday rental in Middleburg

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

6 bedrooms
5 bathrooms
Sleeps 16
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Middleburg

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

6 bedrooms
3 bathrooms
Sleeps 14
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Weekend getaway short distance from DC/Northern Virginia, holiday rental in Middleburg

Weekend getaway short distance from DC/Northern Virginia

1 bedroom
1 bathroom
Sleeps 4
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Gorgeous English Hunt Country Cottage, holiday rental in Middleburg

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
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Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres, holiday rental in Middleburg

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

3 bedrooms
2 bathrooms
Sleeps 8
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This charming and spacious home on 1.5 acres..SLEEPS 22-36 NEARBY COTTAGE, holiday rental in Middleburg

This charming and spacious home on 1.5 acres..SLEEPS 22-36 NEARBY COTTAGE

5 bedrooms
2 bathrooms
Sleeps 22
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Where Charming local history meets modern comfort.  Historic Fauquier County VA, holiday rental in Middleburg

Where Charming local history meets modern comfort. Historic Fauquier County VA

4 bedrooms
3 bathrooms
Sleeps 13
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Middleburg

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

1 bedroom
1 bathroom
Sleeps 2
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Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., holiday rental in Middleburg

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

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

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

4 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Middleburg

Virginia Wine Country Retreat 60 mi. from DC

4 bedrooms
4 bathrooms
Sleeps 10
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Alpacas & The Stars at night. Private Retreat. Fun & Peace, holiday rental in Middleburg

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

3 bedrooms
1 bathroom
Sleeps 6
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in Middleburg

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 Middleburg

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Middleburg

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

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Paradise in Horse Country, holiday rental in Middleburg

Paradise in Horse Country

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

Historic Mountain Cottage at Blue Ridge Overlook

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

Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

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

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Cottage on King St | Historic Charm | Modern Living, holiday rental in Middleburg

Cottage on King St | Historic Charm | Modern Living

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Restored 1820 Waterford Village Farmhouse, holiday rental in Middleburg

Restored 1820 Waterford Village Farmhouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Middleburg

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 Middleburg

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Middleburg

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sheraton Vistiana, holiday rental in Middleburg

Sheraton Vistiana

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Suite w/Private Patio & Entrance In Wine & Horse Country, holiday rental in Middleburg

Beautiful Suite w/Private Patio & Entrance In Wine & Horse Country

1 bedroom
1 bathroom
Sleeps 2
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Couple's romantic getaway, holiday rental in Middleburg

Couple's romantic getaway

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Premier property(s) sleeps 36...So Close in yet very private., holiday rental in Middleburg

Premier property(s) sleeps 36...So Close in yet very private.

10 bedrooms
6 bathrooms
Sleeps 35
Match: Sleeps
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DonRea Villa, holiday rental in Middleburg

DonRea Villa

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Farm View Cottage, holiday rental in Middleburg

Farm View Cottage

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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'Thomson Farm' Classic Home < 10 Mi to Vineyards!, holiday rental in Middleburg

'Thomson Farm' Classic Home < 10 Mi to Vineyards!

7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Tentrr Signature Site - Nut Orchard Retreat, holiday rental in Middleburg

Tentrr Signature Site - Nut Orchard Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg, holiday rental in Middleburg

East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful | Luxury |Fast WiFi |Parking |Movie Theater, holiday rental in Middleburg

Beautiful | Luxury |Fast WiFi |Parking |Movie Theater

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Chic Chantilly Villa: Wineries + DC Museums, holiday rental in Middleburg

NEW! Chic Chantilly Villa: Wineries + DC Museums

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Entire Condominium House 2 King-bed 4 Guest, holiday rental in Middleburg

Entire Condominium House 2 King-bed 4 Guest

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Family Retreat w/ Deck Near Appalachian Trail, holiday rental in Middleburg

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 Middleburg

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 Middleburg

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

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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