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This farm is located just a two-minute drive from Middleburg's historic downtown, nestled in the countryside amidst vineyards and polo fields. It boasts excellent user, location, and cleanliness ratings, making it a highly recommended choice for travelers. The carriage house offers a unique and charming stay with a capacity for four guests. Amenities include a fully equipped kitchen, air conditioning, a spacious patio, and a beautiful garden, perfect for enjoying the peaceful country setting and exploring nearby attractions.

This charming cottage is located just outside Middleburg, within a 3-mile radius of the National Sporting Library & Museum, Tudor Day Spa, and other attractions. It consistently receives excellent ratings for location, cleanliness, and overall user experience.
The 1,500 square foot cottage comfortably accommodates up to 6 guests with 3 bedrooms and 2 bathrooms. Enjoy a fully equipped kitchen, laundry facilities, a private garden, a barbecue grill, and a terrace, perfect for relaxing and enjoying the tranquility of the surrounding countryside.

This historic stone cottage is located on twelve acres of oak woodland, just two minutes from the town center of Middleburg, Virginia.
This pet-friendly rental offers three bedrooms, two bathrooms, and accommodation for six guests, featuring a full kitchen, air conditioning, a garden, parking, and two stone fireplaces.

The Gate House is a charming cottage located just a short distance from Middleburg's vibrant downtown, offering easy access to shops, restaurants, and wineries. This historic property, part of a larger estate dating back to 1768, boasts excellent user, location, and cleanliness ratings.
The cottage features a cozy den, breakfast area, porch, and a bedroom with a built-in queen-sized bed and a marble bathroom. Guests can enjoy amenities like a fully equipped kitchen, air conditioning, a private garden, parking, and Wi-Fi, as well as activities like walking, cycling, and exploring the surrounding countryside.

This charming vacation rental is situated just minutes from vineyards, Salamander Resort, Goodstone Inn, Upperville, and Shadow Creek, making it an ideal base for exploring the beautiful countryside surrounding Middleburg. This gîte has received excellent ratings for location, cleanliness, and overall experience.
The apartment features a spacious bedroom with a king-size bed, accommodating up to two guests. Enjoy a peaceful and secluded stay with access to a swimming pool, gardens, and a large outdoor seating and dining area.

This secluded 10-acre estate in Virginia's horse and wine country is located 4 miles from downtown Middleburg and 5 miles from Salamander Resort.
This bright and exceptionally clean loft apartment offers woodland views, a private swimming pool, and a fire pit, accommodating up to 3 guests with internet, air conditioning, and parking.

This modern 2-bedroom, 2-bathroom apartment is located on a 30-acre horse farm bordering downtown Middleburg, offering easy access to shops, restaurants, and historical sites.
The 3-bedroom rental boasts a fully equipped kitchen with induction cooking, two full bathrooms, spacious wooden decks with pasture views, and accommodates up to five guests.

This studio apartment is located just minutes from Middleburg village, offering convenient access to the Salamander Resort, local vineyards, and a direct route to Washington D.C. and Dulles Airport.
This pet-friendly studio features a fully equipped kitchen, a queen-sized bed, private laundry, and a fenced backyard with garden seating and an optional fire pit, accommodating up to two guests.

This Hunt Country cottage in Bull Run Mountain Estates is uniquely located within a working farm's stable complex, offering views of horse paddocks and is a short five-minute drive from three wineries, close to the historic villages of Middleburg, Aldie, Upperville, and The Plains, and convenient to Sky Meadows State Park and the Great Meadow Foundation event center.
This two-bedroom, one-bathroom vacation home sleeps four, features a combined living room and kitchen with French doors opening onto a patio, in-cottage laundry, and queen-sized beds with plantation shutters; enjoy wine tasting, hiking, and attending events nearby.

This charming studio apartment is located in The Plains, Virginia, just a 10-minute drive from the equestrian towns of Middleburg, Upperville, and Marshall, offering a peaceful escape in Virginia's horse country. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The studio features a private bedroom with a queen bed, a double bed and a single trundle bed in the main living area, accommodating up to four guests. The fully equipped kitchenette includes a refrigerator, oven, toaster oven, Vita-Mix blender, and microwave, allowing guests to prepare their own meals, while the private courtyard and parking provide additional space for relaxation and convenience.

This charming farmhouse is located on a private 22-acre estate bordering Goose Creek, just 5 minutes from downtown Middleburg and the Salamander Spa. Guests consistently rate the location, cleanliness, and overall experience as excellent. The 3000 square foot home features three bedrooms in the main house and an additional guest cottage, sleeping up to 8 guests. Modern amenities include a fully equipped kitchen, a rain shower, a large-screen TV, and a private chef service option, plus guests can enjoy walks along Goose Creek, explore the surrounding countryside, and relax on the historic stone patio.

Quaker Cottage, a pet-friendly Middleburg vacation rental located on Loudoun County's oldest road within a 620-acre farm near Middleburg's town center, offers a secluded escape with walking trails and proximity to historic sites.
This two-story, two-bedroom, one-bathroom house sleeps five, features a fully equipped kitchen with basic supplies, a washer/dryer, air conditioning, and on-site horse boarding (for a fee).

This charming cottage is located just minutes from the heart of Middleburg, offering a peaceful escape from the town's bustle while still being close to its shops, restaurants, and attractions. It boasts excellent ratings for location, cleanliness, and user experience.
The cottage, a converted 200-year-old bank barn, sleeps two guests in one bedroom and one bathroom. Guests can enjoy a fully equipped kitchen, a private garden, a deck overlooking pastures, and the possibility of horseback riding on the same property as the nearby Hunters Retreat.

This Middleburg, Virginia cottage rental sits on 10 acres, a 10-minute drive from the town's center and award-winning wineries and breweries.
The three-bedroom, two-bathroom house sleeps six and features a fully equipped kitchen with dishwasher, air conditioning, a private garden, ample parking, and internet access; enjoy on-site pond walks and nearby Middleburg attractions.