Middleburg vacation rentals

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Best Middleburg vacation rentals

Most recommended vacation rentals in Middleburg

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Magnificent Middleburg Getaway - Middleburg - Building
Magnificent Middleburg Getaway
Middleburg, VA
9.5Wonderful(7)
Parking
Free Wi-Fi
$435+
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Elegant Middleburg Manor with 3 Bedrooms 2 Baths - Middleburg - Living room
Elegant Middleburg Manor with 3 Bedrooms 2 Baths
Middleburg, VA
$2,702+
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Charming Writer's Cottage In The Heart Of Middleburg - Middleburg - Living room
Charming Writer's Cottage In The Heart Of Middleburg
Middleburg, VA
Free Wi-Fi
Pet friendly
$335+
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Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg - Middleburg - Living room
Historical Manor 2 bedroom Unit - Minutes from downtown Middleburg
Middleburg, VA
Free Wi-Fi
$244+
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Hunt Box-Antique Filled Cottage On Lowelands Farm-Middleburg\nzonr-2024-012704 - Middleburg - Bedroom
Hunt Box-Antique Filled Cottage On Lowelands Farm-Middleburg\nzonr-2024-012704
Middleburg, VA
9.9Wonderful(32)
$581+
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Cedar Lane - Private Cottage, Sophisticated Country Charm - Middleburg - Living room
Cedar Lane - Private Cottage, Sophisticated Country Charm
Middleburg, VA
$716+
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Pristine Middleburg Home With 2 Bedrooms 1 Bath - Middleburg - Living room
Pristine Middleburg Home With 2 Bedrooms 1 Bath
Middleburg, VA
$2,685+
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Historic Middleburg Equestrian Estate - Middleburg - Living room
Historic Middleburg Equestrian Estate
Middleburg, VA
Parking
Free Wi-Fi
$2,175+
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Luxury Middleburg Manor with 4 Bedrooms 2 Baths - Middleburg - Living room
Luxury Middleburg Manor with 4 Bedrooms 2 Baths
Middleburg, VA
$651+
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18th Century Stone Cottage minutes from historic Middleburg - Middleburg - Patio
18th Century Stone Cottage minutes from historic Middleburg
Middleburg, VA
Free Wi-Fi
$410+
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Secluded Leesburg Retreat w/ Private Hot Tub! - Middleburg - Bedroom
Secluded Leesburg Retreat w/ Private Hot Tub!
Middleburg, VA
10Wonderful(4)
Free Wi-Fi
$829+
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Littlefield Cottage - Middleburg - Bedroom
Littlefield Cottage
Middleburg, VA
Free Wi-Fi
$732+
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Middleburg Famous Horse Farm - Middleburg - Building
Middleburg Famous Horse Farm
Middleburg, VA
Pool
$932+
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Yellowwood Cottage - Private Outdoor Space Sophisticated Sunny Luxurious Indoor - Middleburg - Dining room
Yellowwood Cottage - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Middleburg, VA
$866+
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Middleburg - Charming Cottage - 5 min to center of M'burg - Middleburg
Middleburg - Charming Cottage - 5 min to center of M'burg
Middleburg, VA
Pet friendly
$237+
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5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath. - Middleburg
5 Min to center of Middleburg - Private Guest Suite w/private entrance & bath.
Middleburg, VA
Pet friendly
$230+
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$230 - $848$848 - $1,466$1,466 - $2,084$2,084 - $2,702$2,702+ per night

Property Types

ApartmentCottageHouse

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Free cancellationFree breakfastFree parkingFree internet
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Good to know

Low season

March

High season

October

Average price (weeknight)

$625

Average price (weekend night)

$525
Cheapest month to stay with an average 82% drop in price.
Most expensive month to stay with an average 212% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Middleburg vacation rental deals

  • The best vacation rental properties in Middleburg are Yellowwood Cottage - Private Outdoor Space Sophisticated Sunny Luxurious Indoor (9.9, 35 reviews), Hunt Box-Antique Filled Cottage On Lowelands Farm-Middleburg\nzonr-2024-012704 (9.9, 32), and Cedar Lane - Private Cottage, Sophisticated Country Charm (9.8, 39), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Middleburg for 2 days.

FAQs when booking a vacation home in Middleburg

  • What types of vacation rentals are available in Middleburg?

    There are loads of different property types that you can make your vacation home in Middleburg. You’ll find apartments, barns, cabins, cottages, farm stays, houses and villas.

  • Are there any pet-friendly vacation rentals in Middleburg?

    There are a number of dog and pet-friendly Middleburg vacation rentals, with around 14% allowing you to bring your pet along with you.

  • How much is a vacation rental in Middleburg for this weekend?

    In the last 72 hours, users have found Middleburg vacation rentals for this weekend for as low as $2,700 per night. Search here for similar prices

  • How can I find vacation rentals near me in Middleburg?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Middleburg?

Our map will help you find the perfect place to stay in Middleburg by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Middleburg

Middleburg vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Middleburg. Find cheap vacation homes to rent in Middleburg. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Middleburg that suits you best.

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