Historic Equestrian Estate in Middleburg Hunt Country

Top rated by guests
Pool
Private kitchen
Private kitchen
Pool
Exterior
review stars
10Outstanding
(20 Ratings)
"Incredible property, excellent communications and logistics. Highly recommend."
B P.
Don't miss out! Price and availability may change
10 / 10
Outstanding(20 Ratings)

House in Shenandoah Valley, VA

10 guests · 5 bedrooms · 5 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Forget your worries in this spacious and serene equestrian estate. Historic White Oaks Farm dates back to the 1800s and offers a glimpse into the famed Middleburg mystique, where the Kennedy’s spent their weekends riding horses and foxhunting. Create your own memories in the resort-like setting, fully equipped with an outdoor kitchen, stunning pool, cabana, outdoor dining areas, hiking trails and lush gardens. Enjoy views out every window of grazing horses and majestic 100-year old oak trees.

This historic horse farm is centrally located and is under 10 minutes to Goodstone Inn, the Salamander Resort and Spa and charming downtown Middleburg. The surrounding areas offer fine dining, wineries, breweries, antiquing, hiking, steeplechase racing, and exciting polo matches. This location, with it’s paved road and nearby connecting dirt roads, is a cyclist’s paradise. Now offering high-speed Starlink internet!

Mountville Road is situated in an ideal corridor offering easy access to Middleburg and Leesburg and is only 35 min to Washington Dulles International Airport. You can hop on the Dulles Toll Road and be to Georgetown in under an hour. Yet, you are just minutes away from the charming towns that dot the countryside, including Unison, Bluemont, Airmont, Aldie, Upperville and beyond.

The second you enter the gates of White Oaks, you feel transported back to a more peaceful and carefree time. As you approach the main home, you will pass the courtyard horse stables. The original stone house dates back to the 1800s and an addition created a large, modern and open kitchen with a formal dining room, formal living room, and spacious theater room with a large wine cellar.

The kitchen opens up onto an outdoor covered patio with a large dining table and chairs overlooking the expansive gardens and stone walls. From there, you can enjoy access to the attached sun room, complete with ceiling fans, stone walls, and a comfortable lounging sectional. The sunroom’s doors open out to the back lawns and pool as well as into the formal indoor dining room, which boasts a wood-burning fireplace.

The living room opens onto the back patio and offers views into the front and back gardens with towering oak trees. This Restoration Hardware room is equipped with a gas fireplace, setting a perfect tone for morning coffee or cozy evenings.

The library has views of the horse paddocks and front gardens and faces the front walkways and front door and offers a small couch, desk, flatscreen TV, and wood-burning fireplace.

Attached to the library is a large office and gym space offering a mudroom, a half bath and another side entrance door. There are two staircases leading upstairs, where you will find the spacious master suite with attached bath, a separate large Roman spa tub and shower, a lounge room, and the laundry room.

Upstairs there are also four guest bedrooms that share two fully renovated bathrooms between them. Two bedrooms offer stunning views of the pool and gardens, and the other two bedrooms offer sweeping views of the scenic front horse pastures and lawns.

You may have as much or as little interaction with the horses onsite as you would like. There are plenty of opportunities for horse petting and carrot-feeding.

Amenities

Non-smoking
No pets allowed
Family friendly

Map of Shenandoah Valley, VA


Ratings and reviews

10 / 10
Outstanding(20 Ratings)
10 / 10Outstanding·May 2026
Incredible property, excellent communications and logistics. Highly recommend.
10 / 10Outstanding·May 2026
I hosted a woman’s weekend at the home. The property was so lovely and the weather turned out perfectly so we could utilize all of the exterior amenities that the house offered. We were able to use the pool and the grill and dinner outside, which was ideal. The horses just added the best touch to the most beautiful home in Virginia. The town of Middleburg is also adorable. The house was perfectly located 11 minutes away also nearby attractions such as Goodstone Inn and Stone Tower winery were in relatively close distance.
10 / 10Outstanding·Feb 2026
The amenities, location and host could not have been better. A truly exceptional stay!
10 / 10Outstanding·Oct 2025
Beautiful property

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Historic Equestrian Estate in Middleburg Hunt Country. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Historic Equestrian Estate in Middleburg Hunt Country pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Historic Equestrian Estate in Middleburg Hunt Country?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.


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