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Hillsboro Holiday Rentals

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50 rentals in Hillsboro.
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Stunning 3 BR/ 2 BA Mountainside Chalet, holiday rental in Hillsboro

Stunning 3 BR/ 2 BA Mountainside Chalet

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Shannondale Lake House, holiday rental in Hillsboro

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 Hillsboro

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 Hillsboro

The Love Cottage in Harpers Ferry by the lake!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Travelers Rest in Harpers Ferry by the lake, holiday rental in Hillsboro

The Travelers Rest in Harpers Ferry by the lake

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Manor House on Shenandoah River in Virginia's Wine Country, holiday rental in Hillsboro

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 Hillsboro

A Restored Wagon Barn On A 1790's Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Countryside Home, holiday rental in Hillsboro

The Countryside Home

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

Gorgeous English Hunt Country Cottage

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

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

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!, holiday rental in Hillsboro

Paradise View OF THE Shenandoah Mountains Wineries and Breweries!!

4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Historic Artist's Cottage on 5 Acre Property Near Blue Ridge Mts. and Wineries, holiday rental in Hillsboro

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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Breathtaking views  with an  indoor private pool, come escape with us, holiday rental in Hillsboro

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

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Family-friendly, centrally located, quiet, updated, historic home built in 1890., holiday rental in Hillsboro

Family-friendly, centrally located, quiet, updated, historic home built in 1890.

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, holiday rental in Hillsboro

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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RIVERFRONT COTTAGE (The Neon Moon), holiday rental in Hillsboro

RIVERFRONT COTTAGE (The Neon Moon)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Blue Ridge Beauty, River Excitement, Wineries, Breweries, Casino, holiday rental in Hillsboro

Blue Ridge Beauty, River Excitement, Wineries, Breweries, Casino

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private Secluded Estate on 13 Acres, holiday rental in Hillsboro

Private Secluded Estate on 13 Acres

7 bedrooms
9 bathrooms
Sleeps 33
Match: Sleeps
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Romantic Shabby Chic Cottage on 5 Acre Property Near Wineries and Blue Ridge Mts, holiday rental in Hillsboro

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 Hillsboro

Meadowbrook -Entire House - Close to Vineyards and Breweries

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Renovated Mountain Basement Studio Near Wineries Breweries w/ Laundry & Fire Pit, holiday rental in Hillsboro

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic Booth House at the Harpers Ferry KOA, holiday rental in Hillsboro

Historic Booth House at the Harpers Ferry KOA

6 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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The McCoy House at the Harpers Ferry/Civil War Battlefields KOA, holiday rental in Hillsboro

The McCoy House at the Harpers Ferry/Civil War Battlefields KOA

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Restored 1820 Waterford Village Farmhouse, holiday rental in Hillsboro

Restored 1820 Waterford Village Farmhouse

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Titicaca Room, holiday rental in Hillsboro

Titicaca Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dome Of Your Dreams!, holiday rental in Hillsboro

Dome Of Your Dreams!

2 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Maple Hill Farm within minutes of Vineyards, Wedding Venues and Horse Stables, holiday rental in Hillsboro

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 Hillsboro

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 Hillsboro

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

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Downtown Charles Town Condo w/ Laundry Above Abolitionist Ale Works #202, holiday rental in Hillsboro

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic House Close to The Potomac River / C&O Canal / Appalachian Trail, holiday rental in Hillsboro

Historic House Close to The Potomac River / C&O Canal / Appalachian Trail

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Blueridge Cabin!, holiday rental in Hillsboro

The Blueridge Cabin!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Shanandoah Room, holiday rental in Hillsboro

Shanandoah Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Shallows Room, holiday rental in Hillsboro

Shallows Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Country Cottage with Super Location All Private Suite & Breakfast Included, holiday rental in Hillsboro

Country Cottage with Super Location All Private Suite & Breakfast Included

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Your own  amazing10,000s/f Mansion in the Heart of Wine Country w/Guitar Pool, holiday rental in Hillsboro

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

9 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Private One Bedroom Condo in Historic Downtown Charles Town Above Microbrewery, holiday rental in Hillsboro

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 Hillsboro

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Potomac Room, holiday rental in Hillsboro

Potomac Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 2, holiday rental in Hillsboro

Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 1, holiday rental in Hillsboro

Tentrr Signature Site - Harpers Ferry - Potomac River View Campsite 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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3 Bed Harpers Ferry Mountain Retreat w/ Fire Pit, holiday rental in Hillsboro

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 Hillsboro

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 Hillsboro

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 Hillsboro

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 Hillsboro

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

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Harpers Ferry Cabin w Deck/Grill, Game Room, WiFi!, holiday rental in Hillsboro

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

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Enchanting Cottage, Center of Historic Downtown!, holiday rental in Hillsboro

Enchanting Cottage, Center of Historic Downtown!

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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La Soledad Lavender Farm and Guesthouse, holiday rental in Hillsboro

La Soledad Lavender Farm and Guesthouse

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Cottage At Historical Waterford Close to Wineries!, holiday rental in Hillsboro

Charming Cottage At Historical Waterford Close to Wineries!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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