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Round Hill Vacation Rentals

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50 rentals in Round Hill.
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'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Round Hill
'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Round Hill
'Anny's Farm House' in Round Hill Wine Country!, vacation rental in Round Hill

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Countryside Home, vacation rental in Round Hill
The Countryside Home, vacation rental in Round Hill
The Countryside Home, vacation rental in Round Hill

The Countryside Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous English Hunt Country Cottage, vacation rental in Round Hill
Gorgeous English Hunt Country Cottage, vacation rental in Round Hill
Gorgeous English Hunt Country Cottage, vacation rental in Round Hill

Gorgeous English Hunt Country Cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Manor House on Shenandoah River in Virginia's Wine Country

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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A Restored Wagon Barn On A 1790's Farm, vacation rental in Round Hill
A Restored Wagon Barn On A 1790's Farm, vacation rental in Round Hill
A Restored Wagon Barn On A 1790's Farm, vacation rental in Round Hill

A Restored Wagon Barn On A 1790's Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming, Cozy, Secluded Mountain Cabin, vacation rental in Round Hill
Charming, Cozy, Secluded Mountain Cabin, vacation rental in Round Hill
Charming, Cozy, Secluded Mountain Cabin, vacation rental in Round Hill

Charming, Cozy, Secluded Mountain Cabin

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, vacation rental in Round Hill
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, vacation rental in Round Hill
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg, vacation rental in Round Hill

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Cottage at Twin Notch Farm, vacation rental in Round Hill
The Cottage at Twin Notch Farm, vacation rental in Round Hill
The Cottage at Twin Notch Farm, vacation rental in Round Hill

The Cottage at Twin Notch Farm

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic and Updated Farmhouse Built in 1808, vacation rental in Round Hill
Historic and Updated Farmhouse Built in 1808, vacation rental in Round Hill
Historic and Updated Farmhouse Built in 1808, vacation rental in Round Hill

Historic and Updated Farmhouse Built in 1808

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Vineyard View Lodge, vacation rental in Round Hill
Vineyard View Lodge, vacation rental in Round Hill
Vineyard View Lodge, vacation rental in Round Hill

Vineyard View Lodge

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, vacation rental in Round Hill
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, vacation rental in Round Hill
Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, vacation rental in Round Hill

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Riverfront Getaway w/ Breathtaking Views!, vacation rental in Round Hill
Riverfront Getaway w/ Breathtaking Views!, vacation rental in Round Hill
Riverfront Getaway w/ Breathtaking Views!, vacation rental in Round Hill

Riverfront Getaway w/ Breathtaking Views!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, vacation rental in Round Hill
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, vacation rental in Round Hill
Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, vacation rental in Round Hill

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

Rental Home
6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Country Cottage on 1700’s Horse Farm/Wedding Venue, vacation rental in Round Hill
Country Cottage on 1700’s Horse Farm/Wedding Venue, vacation rental in Round Hill
Country Cottage on 1700’s Horse Farm/Wedding Venue, vacation rental in Round Hill

Country Cottage on 1700’s Horse Farm/Wedding Venue

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Stunning 3 BR/ 2 BA Mountainside Chalet, vacation rental in Round Hill
Stunning 3 BR/ 2 BA Mountainside Chalet, vacation rental in Round Hill
Stunning 3 BR/ 2 BA Mountainside Chalet, vacation rental in Round Hill

Stunning 3 BR/ 2 BA Mountainside Chalet

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Breathtaking views  with an  indoor private pool, come escape with us, vacation rental in Round Hill
Breathtaking views  with an  indoor private pool, come escape with us, vacation rental in Round Hill
Breathtaking views  with an  indoor private pool, come escape with us, vacation rental in Round Hill

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Guest House at 1796 Historic Plantation Farm in Wine Country, vacation rental in Round Hill
Guest House at 1796 Historic Plantation Farm in Wine Country, vacation rental in Round Hill
Guest House at 1796 Historic Plantation Farm in Wine Country, vacation rental in Round Hill

Guest House at 1796 Historic Plantation Farm in Wine Country

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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2nd Floor, Efficiency, Private Entrance, vacation rental in Round Hill
2nd Floor, Efficiency, Private Entrance, vacation rental in Round Hill
2nd Floor, Efficiency, Private Entrance, vacation rental in Round Hill

2nd Floor, Efficiency, Private Entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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RIVERFRONT COTTAGE (The Neon Moon), vacation rental in Round Hill
RIVERFRONT COTTAGE (The Neon Moon), vacation rental in Round Hill
RIVERFRONT COTTAGE (The Neon Moon), vacation rental in Round Hill

RIVERFRONT COTTAGE (The Neon Moon)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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River House Near Harpers Ferry!, vacation rental in Round Hill
River House Near Harpers Ferry!, vacation rental in Round Hill
River House Near Harpers Ferry!, vacation rental in Round Hill

River House Near Harpers Ferry!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, vacation rental in Round Hill
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, vacation rental in Round Hill
Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view, vacation rental in Round Hill

Monet HoneymoonSuite Elegant Lrg 2rm w/balcony in villa/Mountn~pasture-pool view

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, vacation rental in Round Hill
Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, vacation rental in Round Hill
Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, vacation rental in Round Hill

Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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1805 Farmhouse Luxury Renovation in Harpers Ferry, vacation rental in Round Hill
1805 Farmhouse Luxury Renovation in Harpers Ferry, vacation rental in Round Hill
1805 Farmhouse Luxury Renovation in Harpers Ferry, vacation rental in Round Hill

1805 Farmhouse Luxury Renovation in Harpers Ferry

Rental Home
5 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
More info
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Quiet Mountain Getaway Minutes from Hiking and Wineries!, vacation rental in Round Hill
Quiet Mountain Getaway Minutes from Hiking and Wineries!, vacation rental in Round Hill
Quiet Mountain Getaway Minutes from Hiking and Wineries!, vacation rental in Round Hill

Quiet Mountain Getaway Minutes from Hiking and Wineries!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Romantic, Secluded, Rustic Mtn. Cabin in the Woods, vacation rental in Round Hill
Romantic, Secluded, Rustic Mtn. Cabin in the Woods, vacation rental in Round Hill
Romantic, Secluded, Rustic Mtn. Cabin in the Woods, vacation rental in Round Hill

Romantic, Secluded, Rustic Mtn. Cabin in the Woods

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Round Hill
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Round Hill
Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, vacation rental in Round Hill

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

Rental Home
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Paradise in Horse Country, vacation rental in Round Hill
Paradise in Horse Country, vacation rental in Round Hill
Paradise in Horse Country, vacation rental in Round Hill

Paradise in Horse Country

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy Cabin Hidden Away on a Lake!, vacation rental in Round Hill
Cozy Cabin Hidden Away on a Lake!, vacation rental in Round Hill
Cozy Cabin Hidden Away on a Lake!, vacation rental in Round Hill

Cozy Cabin Hidden Away on a Lake!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Round Hill
Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Round Hill
Historic Mountain Cottage at Blue Ridge Overlook, vacation rental in Round Hill

Historic Mountain Cottage at Blue Ridge Overlook

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Restored 1820 Waterford Village Farmhouse, vacation rental in Round Hill
Restored 1820 Waterford Village Farmhouse, vacation rental in Round Hill
Restored 1820 Waterford Village Farmhouse, vacation rental in Round Hill

Restored 1820 Waterford Village Farmhouse

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Your 6000s/f resort 2000s/f deck-Hot tub-Sauna-Arcade games-15 acres, vacation rental in Round Hill
Your 6000s/f resort 2000s/f deck-Hot tub-Sauna-Arcade games-15 acres, vacation rental in Round Hill
Your 6000s/f resort 2000s/f deck-Hot tub-Sauna-Arcade games-15 acres, vacation rental in Round Hill

Your 6000s/f resort 2000s/f deck-Hot tub-Sauna-Arcade games-15 acres

Rental Home
8 bedrooms
5 bathrooms
Sleeps 22
Match: Sleeps
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The Van Gogh Room in Villa, vacation rental in Round Hill
The Van Gogh Room in Villa, vacation rental in Round Hill
The Van Gogh Room in Villa, vacation rental in Round Hill

The Van Gogh Room in Villa

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, vacation rental in Round Hill
The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, vacation rental in Round Hill
The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, vacation rental in Round Hill

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Shannondale Lake House, vacation rental in Round Hill
Shannondale Lake House, vacation rental in Round Hill
Shannondale Lake House, vacation rental in Round Hill

Shannondale Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Dome Of Your Dreams!, vacation rental in Round Hill
Dome Of Your Dreams!, vacation rental in Round Hill
Dome Of Your Dreams!, vacation rental in Round Hill

Dome Of Your Dreams!

Rental Home
2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, vacation rental in Round Hill
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, vacation rental in Round Hill
Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, vacation rental in Round Hill

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Apt in Harpers Ferry by the lake!, vacation rental in Round Hill
Cozy Apt in Harpers Ferry by the lake!, vacation rental in Round Hill
Cozy Apt in Harpers Ferry by the lake!, vacation rental in Round Hill

Cozy Apt in Harpers Ferry by the lake!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Love Cottage in Harpers Ferry by the lake!, vacation rental in Round Hill
The Love Cottage in Harpers Ferry by the lake!, vacation rental in Round Hill
The Love Cottage in Harpers Ferry by the lake!, vacation rental in Round Hill

The Love Cottage in Harpers Ferry by the lake!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Hunt Box on 1700's Horse Farm/Wedding Venue, vacation rental in Round Hill
Hunt Box on 1700's Horse Farm/Wedding Venue, vacation rental in Round Hill
Hunt Box on 1700's Horse Farm/Wedding Venue, vacation rental in Round Hill

Hunt Box on 1700's Horse Farm/Wedding Venue

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Blueridge Cabin!, vacation rental in Round Hill
The Blueridge Cabin!, vacation rental in Round Hill
The Blueridge Cabin!, vacation rental in Round Hill

The Blueridge Cabin!

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Don Rea Luxury Villa, vacation rental in Round Hill
Don Rea Luxury Villa, vacation rental in Round Hill
Don Rea Luxury Villa, vacation rental in Round Hill

Don Rea Luxury Villa

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Hidden View - All 5-Suites, vacation rental in Round Hill
Hidden View - All 5-Suites, vacation rental in Round Hill
Hidden View - All 5-Suites, vacation rental in Round Hill

Hidden View - All 5-Suites

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, vacation rental in Round Hill
Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, vacation rental in Round Hill
Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, vacation rental in Round Hill

Your own amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool

Rental Home
9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Karens Cottage, vacation rental in Round Hill
Karens Cottage, vacation rental in Round Hill
Karens Cottage, vacation rental in Round Hill

Karens Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Lake View Retreat - Contemporary Cottage Near a Peaceful Lake!, vacation rental in Round Hill
Lake View Retreat - Contemporary Cottage Near a Peaceful Lake!, vacation rental in Round Hill
Lake View Retreat - Contemporary Cottage Near a Peaceful Lake!, vacation rental in Round Hill

Lake View Retreat - Contemporary Cottage Near a Peaceful Lake!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, vacation rental in Round Hill
Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, vacation rental in Round Hill
Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability, vacation rental in Round Hill

Entire Log Cabin Vacation Rental 4 Bedroom contact us for availability

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Farm View Cottage With Pond, vacation rental in Round Hill
Farm View Cottage With Pond, vacation rental in Round Hill
Farm View Cottage With Pond, vacation rental in Round Hill

Farm View Cottage With Pond

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Travelers Rest in Harpers Ferry by the lake, vacation rental in Round Hill
The Travelers Rest in Harpers Ferry by the lake, vacation rental in Round Hill
The Travelers Rest in Harpers Ferry by the lake, vacation rental in Round Hill

The Travelers Rest in Harpers Ferry by the lake

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cabin w Hot Tub, Deck/Grill, Game Room,WiFi!, vacation rental in Round Hill
Cabin w Hot Tub, Deck/Grill, Game Room,WiFi!, vacation rental in Round Hill
Cabin w Hot Tub, Deck/Grill, Game Room,WiFi!, vacation rental in Round Hill

Cabin w Hot Tub, Deck/Grill, Game Room,WiFi!

Cabin
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Scenic Cottage retreat at historic Buckskin manor, vacation rental in Round Hill
Scenic Cottage retreat at historic Buckskin manor, vacation rental in Round Hill
Scenic Cottage retreat at historic Buckskin manor, vacation rental in Round Hill

Scenic Cottage retreat at historic Buckskin manor

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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