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Holiday Rentals in Berryville

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50 rentals in Berryville.
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The Outpost: a rustic respite in the Shenandoah Valley - 4 Tesla Bikes For Use, holiday rental in Berryville

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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The Outpost Whimsical Farmhouse Retreat +Tesla Charger, holiday rental in Berryville

The Outpost Whimsical Farmhouse Retreat +Tesla Charger

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Outpost Suite 2- A Curated Farmhouse Suite, holiday rental in Berryville

The Outpost Suite 2- A Curated Farmhouse Suite

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Berryville

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 Berryville

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 Berryville

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

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

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

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains, holiday rental in Berryville

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Blue Mountain Log Cabin, holiday rental in Berryville

Blue Mountain Log Cabin

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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City Charmer near Historic OldTown Winchester., holiday rental in Berryville

City Charmer near Historic OldTown Winchester.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hillandale Farmhouse circa 1774 - 6 bedrooms, sleeps 14, newly renovated, holiday rental in Berryville

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

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Hunt Country Cottage, holiday rental in Berryville

Hunt Country Cottage

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Perfect Hunt Box in Clarke Co.  Minutes to Upperville and Middleburg., holiday rental in Berryville

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

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stunning 3 BR/ 2 BA Mountainside Chalet, holiday rental in Berryville

Stunning 3 BR/ 2 BA Mountainside Chalet

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gorgeous English Hunt Country Cottage, holiday rental in Berryville

Gorgeous English Hunt Country Cottage

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Berryville

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 Berryville

RIVERFRONT COTTAGE (The Neon Moon)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Colonial Getaway Near Old Town Historic Winchester, holiday rental in Berryville

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Countryside Home, holiday rental in Berryville

The Countryside Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in Berryville

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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Virginia Wine Country Retreat 60 mi. from DC, holiday rental in Berryville

Virginia Wine Country Retreat 60 mi. from DC

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous, Cozy & Spacious - 20% OFF JAN/09 to APR/02, holiday rental in Berryville

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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River House Near Harpers Ferry!, holiday rental in Berryville

River House Near Harpers Ferry!

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Cozy Cabin Hidden Away on a Lake!, holiday rental in Berryville

Cozy Cabin Hidden Away on a Lake!

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Paradise in Horse Country, holiday rental in Berryville

Paradise in Horse Country

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ruby Summit Point - Your Home at the Track, holiday rental in Berryville

Ruby Summit Point - Your Home at the Track

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit, holiday rental in Berryville

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Meadowbrook -Entire House - Close to Vineyards and Breweries, holiday rental in Berryville

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Stunning Mountain, Vista, and Sunset Views; Theatre, Banquet Hall, holiday rental in Berryville

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

7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301, holiday rental in Berryville

Quiet Renovated Historic Condo Above Abolitionist Ale Works w/ Washer Dryer #301

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Dome Of Your Dreams!, holiday rental in Berryville

Dome Of Your Dreams!

2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Historic Mountain Cottage at Blue Ridge Overlook, holiday rental in Berryville

Historic Mountain Cottage at Blue Ridge Overlook

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Apt in Harpers Ferry by the lake!, holiday rental in Berryville

Cozy Apt in Harpers Ferry by the lake!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Shannondale Lake House, holiday rental in Berryville

Shannondale Lake House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Love Cottage in Harpers Ferry by the lake!, holiday rental in Berryville

The Love Cottage in Harpers Ferry by the lake!

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

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 Berryville

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

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

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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The Blueridge Cabin!, holiday rental in Berryville

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202, holiday rental in Berryville

Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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'Anny's Farm House' in Round Hill Wine Country!, holiday rental in Berryville

'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 Berryville

The Travelers Rest in Harpers Ferry by the lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Just Like Heaven Carriage House, holiday rental in Berryville

Just Like Heaven Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Idyllic Restored 18c cabin Not Available! Wine country! Views*All Amenities., holiday rental in Berryville

Idyllic Restored 18c cabin Not Available! Wine country! Views*All Amenities.

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery, holiday rental in Berryville

Private One Bedroom Condo in Downtown Charles Town Above Future Microbrewery

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town, holiday rental in Berryville

Private and Remodeled Historic 2 Bedroom Condo in Heart of Downtown Charles Town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Fieldstone Farm in Historic Hillsboro, holiday rental in Berryville

Fieldstone Farm in Historic Hillsboro

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Pet-Friendly Home in Heart of Wine Country!, holiday rental in Berryville

Pet-Friendly Home in Heart of Wine Country!

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Shenandoah Stone House With Kayaks & Self Check-in, holiday rental in Berryville

Shenandoah Stone House With Kayaks & Self Check-in

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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ANS Inn and Suites, holiday rental in Berryville

ANS Inn and Suites

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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