Leesburg, Virginia

Vacation Rentals in Leesburg, Virginia

Discover 44 vacation rental properties in Leesburg. From 1 to 7 bedrooms. Average $322/night. 100% have pools.

44 verified listings Book securely on VRBO Prices updated March 2026

44 properties available

Historic and Updated Farmhouse Built in 1808

Historic and Updated Farmhouse Built in 1808

2 beds 1 bath
PoolA/CWiFiBalcony
$241/night
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Private garden cottage located in the heart of downtown.

Private garden cottage located in the heart of downtown.

1 bed 1 bath
PoolA/CWiFiBalcony
$91/night
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Historic Downtown Leesburg, VA. Park your car and walk to everything!!

Historic Downtown Leesburg, VA. Park your car and walk to everything!!

3 beds 2 baths
PoolA/CWiFiBalcony
$151/night
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Landing at The Metropolitan at Village at Leesburg - 2 Bedrooms in Downtown Leesburg

Landing at The Metropolitan at Village at Leesburg - 2 Bedrooms in Downtown Leesburg

2 beds 2 baths
PoolA/CWiFiBalcony
$155/night
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1 bedroom+private bath+free parking+wifi

1 bedroom+private bath+free parking+wifi

1 bed 1 bath
PoolA/CWiFiBalcony
$95/night
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Cozy walkout basement in a quiet townhome with 1 bedroom, 1 parking, wifi

Cozy walkout basement in a quiet townhome with 1 bedroom, 1 parking, wifi

1 bed 1 bath
PoolA/CWiFiBalcony
$95/night
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M&M Suite Near Downtown Leesburg

M&M Suite Near Downtown Leesburg

1 bed 1 bath
PoolA/CWiFiBalcony
$121/night
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This apartment is a 1 bedroom(s), 1 bathrooms, located in Leesburg, VA.

This apartment is a 1 bedroom(s), 1 bathrooms, located in Leesburg, VA.

1 bath
PoolA/CWiFiBalcony
$156/night
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Landing at The Metropolitan at Village at Leesburg - 2 Bedrooms in Downtown Leesburg

Landing at The Metropolitan at Village at Leesburg - 2 Bedrooms in Downtown Leesburg

2 beds 2 baths
PoolA/CWiFiBalcony
$155/night
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The Cottage on Royal - Historic Leesburg Home

The Cottage on Royal - Historic Leesburg Home

3 beds 2 baths
PoolA/CWiFiBalcony
$221/night
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Playful open spaces. Sleeps 6

Playful open spaces. Sleeps 6

3 beds 3 baths
PoolA/CWiFiBalcony
$552/night
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Privacy on 3 gorgeous acres

Privacy on 3 gorgeous acres

1 bed 1 bath
PoolA/CWiFiBalcony
Price on request
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Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

Mt. Gilead Sunrise- Country Suite close to wineries, breweries & wedding venues

1 bed 1 bath
PoolA/CWiFiBalcony
$168/night
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Historic Downtown Leesburg Townhome

Historic Downtown Leesburg Townhome

3 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home

2 beds 1 bath
PoolA/CWiFiBalcony
$323/night
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Modern Farmhouse Getaway

Modern Farmhouse Getaway

1 bed 1 bath
PoolA/CWiFiBalcony
$271/night
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Charming Cottage convenient to Leesburg. Wineries, Hiking and more.

Charming Cottage convenient to Leesburg. Wineries, Hiking and more.

1 bed 1 bath
PoolA/CWiFiBalcony
$236/night
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Historic Charmer - Downtown Leesburg

Historic Charmer - Downtown Leesburg

3 beds 3 baths
PoolA/CWiFiBalcony
$279/night
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Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

3 beds 1 bath
PoolA/CWiFiBalcony
$272/night
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Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

Historic 180 Acre Estate In The Hunt Country Of Loudoun County, Virginia

6 beds 5 baths
PoolA/CWiFiBalcony
$704/night
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New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!

New Wine Horse Country 10 Acre Lux Retreat amid historic sites. Stunning Views!

2 beds 2 baths
PoolA/CWiFiBalcony
$240/night
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Historic Hideaway

Historic Hideaway

2 beds 1 bath
PoolA/CWiFiBalcony
$203/night
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Townhome in Leesburg Historic District!

Townhome in Leesburg Historic District!

2 beds 1 bath
PoolA/CWiFiBalcony
$253/night
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A unique mountaintop getaway overlooking Willow Croft Winery.

A unique mountaintop getaway overlooking Willow Croft Winery.

3 beds 3 baths
PoolA/CWiFiBalcony
$442/night
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CloudView Cottage - Carriage House Apartment

CloudView Cottage - Carriage House Apartment

2 beds 1 bath
PoolA/CWiFiBalcony
$118/night
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Rocky Vines Wine Country Retreat w/ Mountain Views

Rocky Vines Wine Country Retreat w/ Mountain Views

1 bed 1 bath
PoolA/CWiFiBalcony
$175/night
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Luxury 2 bedroom Basement apartment on The Farmhouse

Luxury 2 bedroom Basement apartment on The Farmhouse

1 bed 1 bath
PoolA/CWiFiBalcony
$100/night
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Luxury Retreat with Family Feel: Perfect Getaway!

Luxury Retreat with Family Feel: Perfect Getaway!

4 beds 4 baths
PoolA/CWiFiBalcony
$692/night
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The PINK PEARL in Historic Leesburg

The PINK PEARL in Historic Leesburg

4 beds 2 baths
PoolA/CWiFiBalcony
$603/night
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Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-Leesburg/Brambleton/Aldie area

5 beds 4 baths
PoolA/CWiFiBalcony
$457/night
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Romantic Treehouse Stay in the Sky

Romantic Treehouse Stay in the Sky

1 bed 1 bath
PoolA/CWiFiBalcony
$315/night
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Secluded Leesburg Retreat w/ Private Hot Tub!

Secluded Leesburg Retreat w/ Private Hot Tub!

4 beds 3 baths
PoolA/CWiFiBalcony
$483/night
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Romantic Stone Cottage Circa 1869-75 acres to Hike

Romantic Stone Cottage Circa 1869-75 acres to Hike

1 bed 1 bath
PoolA/CWiFiBalcony
$351/night
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Spacious Virginia Retreat w/ Deck & Scenic Views!

Spacious Virginia Retreat w/ Deck & Scenic Views!

4 beds 2 baths
PoolA/CWiFiBalcony
$425/night
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'Thomson Farm' Classic Home < 10 Mi to Vineyards!

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

7 beds 7 baths
PoolA/CWiFiBalcony
$1,285/night
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The Garage Mahal Virginia

The Garage Mahal Virginia

3 beds 3 baths
PoolA/CWiFiBalcony
$358/night
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Dream Dome Getaway near Leesburg

Dream Dome Getaway near Leesburg

1 bed 1 bath
PoolA/CWiFiBalcony
$234/night
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Duplex Nice Home in Leesburg

Duplex Nice Home in Leesburg

3 beds 1 bath
PoolA/CWiFiBalcony
$331/night
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Spectacular Views & Serene Surroundings: Your Perfect Getaway

Spectacular Views & Serene Surroundings: Your Perfect Getaway

6 beds 5 baths
PoolA/CWiFiBalcony
$804/night
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The Cottage at Oakland Green Farm

The Cottage at Oakland Green Farm

2 beds 2 baths
PoolA/CWiFiBalcony
$257/night
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Beautiful Colonial Duplex 4BR 1BA

Beautiful Colonial Duplex 4BR 1BA

4 beds 1 bath
PoolA/CWiFiBalcony
$272/night
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Spacious single family home!

Spacious single family home!

4 beds 3 baths
PoolA/CWiFiBalcony
$552/night
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Leebsurg 3BR Duplex Home

Leebsurg 3BR Duplex Home

3 beds 1 bath
PoolA/CWiFiBalcony
$178/night
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Leesburg Spacious Home

Leesburg Spacious Home

5 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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