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The Plains Holiday Rentals

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49 rentals in The Plains.
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Beautiful Hunt Country 3 bedroom cottage with large deck and firepit on 3 acres, holiday rental in The Plains

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

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

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Middleburg, VA - Private Cottage, Sophisticated Country Charm  - Newly Remodeled, holiday rental in The Plains

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Mill House in Upperville - Cozy  fireplace, outside bonfire - fall is here!, holiday rental in The Plains

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic and Updated Farmhouse Built in 1808, holiday rental in The Plains

Historic and Updated Farmhouse Built in 1808

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Blue Mountain Log Cabin, holiday rental in The Plains

Blue Mountain Log Cabin

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

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

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

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor, holiday rental in The Plains

Spacious Private Outdoor Space, Sophisticated Modern Sunny and Luxurious Indoor

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hidden Hollow Farm - Pool; Game Rm; Vineyards; 45 min. to DC, Riverwalk & Trails, holiday rental in The Plains

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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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in The Plains

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

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Gorgeous English Hunt Country Cottage, holiday rental in The Plains

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 The Plains

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

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in The Plains

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 The Plains

Weekend getaway short distance from DC/Northern Virginia

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

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

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Where Charming local history meets modern comfort.  Historic Fauquier County VA, holiday rental in The Plains

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

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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This charming and spacious home on 1.5 acres..SLEEPS 22-36 NEARBY COTTAGE, holiday rental in The Plains

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

5 bedrooms
2 bathrooms
Sleeps 22
Match: Sleeps
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Premier luxury Log Cabin Estate, holiday rental in The Plains

Premier luxury Log Cabin Estate

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in The Plains

Virginia Wine Country Retreat 60 mi. from DC

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

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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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in The Plains

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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An upscale log cabin, holiday rental in The Plains

An upscale log cabin

4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in The Plains

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 The Plains

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 The Plains

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 The Plains

Charming 3-Bedroom Farmhouse In Virginia Horse & Wine Country

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Idle Hour at Chester Gap, holiday rental in The Plains

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 The Plains

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 The Plains

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 The Plains

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 The Plains

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 The Plains

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Equipped Suite Near IAD | Free Breakfast + Shuttle to Airport + Corporate Area, holiday rental in The Plains

Equipped Suite Near IAD | Free Breakfast + Shuttle to Airport + Corporate Area

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sheraton Vistiana, holiday rental in The Plains

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 The Plains

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Virginia Wine Country Villa w/Pool & Yard, holiday rental in The Plains

Historic Virginia Wine Country Villa w/Pool & Yard

6 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
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Premier property(s) sleeps 36...So Close in yet very private., holiday rental in The Plains

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

10 bedrooms
6 bathrooms
Sleeps 35
Match: Sleeps
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Pet-Friendly Home in Heart of Wine Country!, holiday rental in The Plains

Pet-Friendly Home in Heart of Wine Country!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Secluded Getaway w/Mtn Views, Deck & Fire Pit, holiday rental in The Plains

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

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spacious Mountain Home: Family, Pet & WFH Friendly, holiday rental in The Plains

Spacious Mountain Home: Family, Pet & WFH Friendly

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Town house near Washington DC Metro Area Near Dulles Airport, holiday rental in The Plains

Town house near Washington DC Metro Area Near Dulles Airport

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful | Luxury |Fast WiFi |Parking |Movie Theater, holiday rental in The Plains

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 The Plains

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 The Plains

Entire Condominium House 2 King-bed 4 Guest

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

Cottage w 2 Private Lakes & River Access, Fire Pit

3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Lakefront Home w/ Canoe, 7 Mi to Front Royal!, holiday rental in The Plains

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

1 bedroom
3 bathrooms
Sleeps 9
Match: Sleeps
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NEW! Chic Ashburn Townhome w/ Balcony, Pool Access, holiday rental in The Plains

NEW! Chic Ashburn Townhome w/ Balcony, Pool Access

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

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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ROOM WITH PRIVATE BATH, holiday rental in The Plains

ROOM WITH PRIVATE BATH

1 bedroom
1 bathroom
Sleeps 1
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