Middleburg, Virginia

Vacation Rentals in Middleburg, Virginia

Discover 19 vacation rental properties in Middleburg. From 1 to 5 bedrooms. Average $401/night. 100% have pools.

19 verified listings Book securely on VRBO Prices updated March 2026

19 properties available

Middleburg - Charming Cottage - 5 min to center of M'burg

Middleburg - Charming Cottage - 5 min to center of M'burg

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

1 bed 1 bath
PoolA/CWiFiBalcony
$271/night
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Historic Equestrian Estate in Middleburg Hunt Country

Historic Equestrian Estate in Middleburg Hunt Country

5 beds 4 baths
PoolA/CWiFiBalcony
$1,557/night
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5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.

5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.

1 bed 1 bath
PoolA/CWiFiBalcony
$145/night
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Charming Writer's Cottage in the Heart of Middleburg

Charming Writer's Cottage in the Heart of Middleburg

1 bed 1 bath
PoolA/CWiFiBalcony
$185/night
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CEDAR LANE - Private Cottage, Sophisticated Country Charm

CEDAR LANE - Private Cottage, Sophisticated Country Charm

2 beds 1 bath
PoolA/CWiFiBalcony
$372/night
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Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

Cosy studio on an organic farm, pet friendly! Just minutes from Middleburg.

1 bath
PoolA/CWiFiBalcony
$163/night
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super cosy cottage with high speed internet!

super cosy cottage with high speed internet!

1 bed 1 bath
PoolA/CWiFiBalcony
$157/night
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Pristine Middleburg Home with 2 Bedrooms 1 Bath

Pristine Middleburg Home with 2 Bedrooms 1 Bath

2 beds 1 bath
PoolA/CWiFiBalcony
$453/night
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YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

4 beds 3 baths
PoolA/CWiFiBalcony
$425/night
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Modern Home on Middleburg Equestrian Farm

Modern Home on Middleburg Equestrian Farm

3 beds 2 baths
PoolA/CWiFiBalcony
$403/night
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Lovely Guest House 2.5 miles from downtown Middleburg

Lovely Guest House 2.5 miles from downtown Middleburg

1 bed 1 bath
PoolA/CWiFiBalcony
$281/night
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Elegant Middleburg Manor with 3 Bedrooms 2 Baths

Elegant Middleburg Manor with 3 Bedrooms 2 Baths

3 beds 2 baths
PoolA/CWiFiBalcony
$512/night
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Hunters Retreat with High Speed Internet

Hunters Retreat with High Speed Internet

3 beds 3 baths
PoolA/CWiFiBalcony
$673/night
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Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg

2 beds 1 bath
PoolA/CWiFiBalcony
$277/night
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Littlefield Cottage

Littlefield Cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$502/night
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Luxury Middleburg Manor with 4 Bedrooms 2 Baths

Luxury Middleburg Manor with 4 Bedrooms 2 Baths

4 beds 2 baths
PoolA/CWiFiBalcony
$564/night
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Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg

3 beds 2 baths
PoolA/CWiFiBalcony
$321/night
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Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops

Magnificent Middleburg Getaway: 2BR w Bucolic Views, Solar Power, & Nearby Shops

2 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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