Holiday Rentals in Middleburg, VA

This studio apartment is situated on a 70-acre horse farm in The Plains, Virginia, just 10 kilometres from the charming towns of The Plains, Middleburg, Upperville, and Marshall, all steeped in equestrian history. The property has received excellent ratings for location, cleanliness and user experience.
The studio apartment can accommodate up to three guests and features a private bedroom with a super queen bed, a double bed in the studio space, and a single bed trundle. Guests can enjoy a well-equipped kitchen, a shared courtyard, and private parking for two cars.

This three-bedroom apartment is situated in the centre of Middleburg, just 0.4 kilometres from the Salamander Resort and the historic district. It has received excellent ratings for its location, cleanliness, and overall experience.
The property can accommodate up to seven guests and features a newly renovated kitchen and master bedroom suite, as well as multiple fireplaces, outdoor living spaces, and ample parking. Guests can enjoy the convenience of a washer and dryer, a propane fire table, and a wood-burning fire pit.

This charming cottage is located in historic Aldie, Virginia, just a short drive from the picturesque town of Middleburg, known for its equestrian events and charming shops. The property boasts excellent user, location, and cleanliness ratings, making it an ideal choice for a peaceful retreat.
The cottage is a unique two-storey property with a bathroom downstairs and a bedroom and kitchen upstairs, sleeping up to two guests. Guests can enjoy a fully equipped kitchen, a private garden, and a porch for relaxing, as well as access to FIOS internet, Roku, and a selection of outdoor activities, including the opportunity to pick flowers or vegetables in season.

This five-bedroom house is situated in Delaplane, Virginia, within 5 kilometres of RdV Vineyards, Delaplane Cellars, and Barrel Oak Winery, making it ideal for wine enthusiasts.
The 251 square metre property offers a private garden, barbecue grills, a Jacuzzi, and an arcade/game room, accommodating up to 14 guests and providing ample space for relaxation and entertainment.

The Saddle Tree loft is situated just outside Middleburg, offering a peaceful countryside retreat with views of rolling hills, pastures, and a pond. This apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The loft features a comfortable king-sized bed and a private bathroom, suitable for a couple seeking a relaxing getaway. Guests can enjoy a well-equipped kitchen, a cosy living area, and a private garden with a fire pit, perfect for evenings spent under the stars.

Bellwether Farm, a self-catering cottage near Upperville, Virginia, is located minutes (approximately 1.6km) from the Upperville Horse Show grounds and is surrounded by prestigious estates, vineyards, and horse farms.
This three-bedroom, one-bathroom property sleeps six guests and boasts a large chef's kitchen with microwave and dishwasher, air conditioning, a garden, parking, and internet access; enjoy the expansive grounds and proximity to Middleburg's attractions.

This renovated 3-bedroom, 3-bathroom farmhouse, offering accommodation for up to 7 guests, is situated on 12 private acres at the end of a gravel road just outside Leesburg, providing a secluded rural retreat 10 kilometres from downtown Leesburg and 24 kilometres from Middleburg, with convenient access to Stone Tower winery.
The property features a fully equipped kitchen with modern appliances, a finished basement with a Queen sleeper sofa, two decks for outdoor enjoyment, and ample driveway parking for 4+ vehicles, making it an ideal base for exploring local wineries, breweries, and trails.

This three-bedroom, two-bathroom flat offers a peaceful retreat in a quiet district of Marshall, ideal for those seeking a tranquil experience near local attractions.
This accommodation for six guests includes air conditioning, kitchen facilities, internet, and parking, promising a comfortable stay with a unique atmosphere.

Villa Maud is a charming house located in Purcellville, Virginia, just 21 miles from Chantilly, 24 miles from Winchester, and 30 miles from Frederick, offering easy access to historical sites, wineries, and other attractions. The property has received very good user ratings and excellent ratings for its location and cleanliness.
The house features one bedroom and a range of amenities, including a swimming pool, jacuzzi, terrace, garden, and spa. Guests can enjoy free Wi-Fi, private parking, and access to a hot tub and outdoor pool.

This restored 1700s farmhouse, offering 186 square meters of living space, is located in Round Hill, a mere 80 kilometres from Washington D.C. and minutes from the Appalachian Trail, Bluemont Winery, Dirt Farm Brewery, and Bear Chase. This family-friendly property sleeps six guests across three bedrooms and four bathrooms, featuring air conditioning, Wi-Fi, a kitchen with a fridge, microwave oven, and dishwasher, and a terrace, making it an ideal base for exploring local heritage sites like the Plaster Museum of Bluemont's Heritage and the Round Hill Arts Centre, as well as family attractions such as Great Country Farms.

The Gate House is a charming cottage located in the Virginia countryside, just a short drive from the historic town of Middleburg. This property has received excellent ratings for its cleanliness, location and overall experience.
The cottage offers a peaceful retreat with a private garden and parking. Guests can enjoy a range of amenities, including a fully equipped kitchen, Wi-Fi, and a comfortable living space.

Annys Farm House is situated in Round Hill Wine Country, just a short drive from Middleburg and within easy reach of major attractions like Manassas National Battlefield Park and Dulles Airport. The property consistently receives excellent ratings for its location, cleanliness and overall experience.
This spacious four-bedroom home offers comfortable accommodation for up to eight guests, with a total floor area of 204 square metres. The house is fully equipped with modern amenities, including a kitchen with a fridge, microwave, dishwasher, and a garden with a spa, perfect for relaxing after a day of exploring the area.