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Round Hill Holiday Rentals

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50 rentals in Round Hill.
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Gorgeous English Hunt Country Cottage, holiday rental in Round Hill

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Countryside Home, holiday rental in Round Hill

The Countryside Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Meadowbrook -Entire House - Close to Vineyards and Breweries, holiday rental in Round Hill

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Round Hill

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

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

A Restored Wagon Barn On A 1790's Farm

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

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 Round Hill

Historic and Updated Farmhouse Built in 1808

2 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 Round Hill

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

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Round Hill

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

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Stunning 3 BR/ 2 BA Mountainside Chalet, holiday rental in Round Hill

Stunning 3 BR/ 2 BA Mountainside Chalet

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Round Hill

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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RIVERFRONT COTTAGE (The Neon Moon), holiday rental in Round Hill

RIVERFRONT COTTAGE (The Neon Moon)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in Round Hill

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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River House Near Harpers Ferry!, holiday rental in Round Hill

River House Near Harpers Ferry!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Paradise in Horse Country, holiday rental in Round Hill

Paradise in Horse Country

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Round Hill

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

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Round Hill

Historic Mountain Cottage at Blue Ridge Overlook

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Gorgeous, Cozy & Spacious - 20% OFF JAN/09 to APR/02, holiday rental in Round Hill

Gorgeous, Cozy & Spacious - 20% OFF JAN/09 to APR/02

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Cabin Hidden Away on a Lake!, holiday rental in Round Hill

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit, holiday rental in Round Hill

Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cottage on King St | Historic Charm | Modern Living, holiday rental in Round Hill

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 Round Hill

Restored 1820 Waterford Village Farmhouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, holiday rental in Round Hill

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 Round Hill

Dome Of Your Dreams!

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

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 Round Hill

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 Round Hill

The Love Cottage in Harpers Ferry by the lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Round Hill

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

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201, holiday rental in Round Hill

1200 SqFt Condo Above Abolitionist Ale Works Charles Town w/ Laundry & Deck #201

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Harpers Ferry Mountain Retreat - 3 Bedroom Near Wineries w/ Laundry & Fire Pit, holiday rental in Round Hill

Harpers Ferry Mountain Retreat - 3 Bedroom Near Wineries w/ Laundry & Fire Pit

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Blueridge Cabin!, holiday rental in Round Hill

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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The Travelers Rest in Harpers Ferry by the lake, holiday rental in Round Hill

The Travelers Rest in Harpers Ferry by the lake

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

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

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Karens Cottage, holiday rental in Round Hill

Karens Cottage

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private One Bedroom Condo in Historic Downtown Charles Town Above Microbrewery, holiday rental in Round Hill

Private One Bedroom Condo in Historic Downtown Charles Town Above Microbrewery

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private Historic 2 Bedroom Condo in Heart of Downtown Charles Town #200, holiday rental in Round Hill

Private Historic 2 Bedroom Condo in Heart of Downtown Charles Town #200

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cabin On The Creek, holiday rental in Round Hill

Cabin On The Creek

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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DonRea Villa, holiday rental in Round Hill

DonRea Villa

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

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 Round Hill

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

7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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The Outpost Suite 2- A Curated Farmhouse Suite, holiday rental in Round Hill

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 Round Hill

The Outpost Whimsical Farmhouse Retreat +Tesla Charger

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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East Wing Row | Beautifully Remodeled Townhouse 5 Mins from DT Leesburg, holiday rental in Round Hill

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

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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3 Bed Harpers Ferry Mountain Retreat w/ Fire Pit, holiday rental in Round Hill

3 Bed Harpers Ferry Mountain Retreat w/ Fire Pit

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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2 Bed Condo w Laundry Above Abolitionist Ale Works in Historic Charles Town #301, holiday rental in Round Hill

2 Bed Condo w Laundry Above Abolitionist Ale Works in Historic Charles Town #301

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Large 2 Bedroom Condo Above Abolitionist Ale Works w/ Laundry & Balcony #201, holiday rental in Round Hill

Large 2 Bedroom Condo Above Abolitionist Ale Works w/ Laundry & Balcony #201

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Historic 2 Bed Condo at Abolitionist Ale Works w/ Laundry & Balcony #300, holiday rental in Round Hill

Historic 2 Bed Condo at Abolitionist Ale Works w/ Laundry & Balcony #300

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Harpers Ferry Private Basement Studio w Laundry, Deck & Fire Pit, holiday rental in Round Hill

Harpers Ferry Private Basement Studio w Laundry, Deck & Fire Pit

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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NEW! Family Retreat w/ Deck Near Appalachian Trail, holiday rental in Round Hill

NEW! Family Retreat w/ Deck Near Appalachian Trail

4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!, holiday rental in Round Hill

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

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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