Compare vacation rentals in Middleburg, VA from 100+ sites!

This charming cottage is located in Middleburg, Virginia, near the river and within easy reach of Sky Meadows State Park and Audubon Naturalist Society Rust Nature Sanctuary. It has received excellent user ratings, making it a popular choice for travelers.
This 600 square foot, one-bedroom cottage comfortably accommodates two guests. It offers a fully equipped kitchen, a spa, a garden, and a European-inspired interior design, all while providing easy access to nearby nature trails, cultural attractions, and local entertainment options.

This newly renovated cottage offers a prime location in Virginia's Hunt Country, just a short drive from Middleburg and Upperville, with sweeping views of the Blue Ridge Mountains.
This two-bedroom, two-bathroom residence accommodates up to four guests and features a fully equipped kitchen with marble countertops, air conditioning, and a front patio.

Serenity Cabin In The Woods, located in Delaplane, Virginia, offers a peaceful woodland setting near the Old Jail Museum (15 miles) and Jiffy Lube Live (21 miles).
This 720-square-foot vacation rental features one bedroom, one bathroom, and can comfortably accommodate up to seven guests, boasting a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, and free on-site parking.

This Shenandoah Retreat apartment is conveniently located in Bluemont, Virginia, just 2.3 miles from Great Country Farms and 2.7 miles from Bluemont Vineyard, with other wineries nearby.
This one-bedroom, one-bathroom unit sleeps three guests and features air conditioning, internet access, and is ideal for exploring the Shenandoah Valley's wineries and attractions.

This charming cottage is located in Aldie, Virginia, just 5 minutes from historic Middleburg and a short drive from Bull Run Mountain Estates, offering a peaceful escape in hunt country. Guests have consistently rated this property excellent for its location, cleanliness, and overall experience.
The one-bedroom, one-bathroom cottage comfortably accommodates two guests. Enjoy amenities like a fully stocked kitchen, a private garden, and pet-friendly accommodations, along with the option to explore the surrounding horse property and nearby attractions.

This charming cottage is located just five minutes outside of Middleburg, offering a peaceful retreat in a quiet, rural setting close to restaurants, shops, and wedding venues. Guests consistently rate the cottage excellent for its cleanliness, location, and overall experience.
The one-bedroom cottage comfortably accommodates two guests and features a modern kitchenette with a refrigerator, microwave, and coffee maker. Enjoy the fresh air and beautiful surroundings on the open lawns and outdoor seating, or bring your furry friend along as pets are welcome.

This 2200 sq ft apartment in Marshall is a 2-minute drive from Marshall Center and a 4-minute drive from Northern Fauquier Community Park, offering convenient access to local attractions.
This 3-bedroom, 3-bathroom residence accommodates up to 6 guests and features a private garden, terrace, barbecue area, Wi-Fi, air conditioning, and a fully equipped kitchen.

This Leesburg apartment is a rural retreat with a garden and a patio. It's located 1.3 miles from Catoctin Valley and within 6 miles of Stone Tower Winery and The Barns at Hamilton Station Vineyards. The apartment has excellent user ratings.
The apartment has one bedroom and one bathroom and can accommodate up to four guests. It has a floor area of 880 square feet and features a fully equipped kitchen, a washing machine, a sofa bed, free WiFi, and air conditioning. Pets are allowed.

This historic cottage is located in Bluemont, Virginia, just an hour from Washington, D.C., and offers stunning views of the Shenandoah Valley and Appalachian Mountains. Guests consistently rate this rental excellent for its location, cleanliness, and overall experience.
The Shenandoah Retreat cottage has two bathrooms and can comfortably accommodate up to seven guests. Enjoy a relaxing stay with amenities like a screened-in porch, a fire pit, a clawfoot tub, and access to local attractions like vineyards, breweries, and the Shenandoah River.

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 family-friendly vacation home in Delaplane is just a short drive from several wineries, including RdV Vineyards, Delaplane Cellars, and Barrel Oak Winery, all within 3 miles. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The 5-bedroom house can comfortably accommodate up to 14 guests, providing ample space for a large family or group of friends. Enjoy the modern kitchen, the relaxing jacuzzi, the spacious garden, and the fun arcade/game room.

This restored 1700s farmhouse in Round Hill is situated less than an hour from Washington D.C. and just minutes from the Appalachian Trail, Bluemont Winery, Dirt Farm Brewery, and Bear Chase.
This 2000-square-foot farm stay accommodates up to 6 guests with 3 bedrooms and 4 bathrooms, featuring a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, and a terrace, offering an ideal base for private getaways or weekend escapes.

This 3-bedroom, 3-bath renovated farmhouse rental in Leesburg is located on 12 private acres at the end of a gravel road, offering a secluded rural retreat just 6 minutes from downtown Leesburg and 15-20 minutes from Middleburg and area wineries.
This family-friendly house accommodates up to 7 guests with a finished basement, features a fully equipped kitchen with modern appliances, offers high-speed internet, smart TVs, and has two decks and ample parking for your convenience.

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.

Annys Farm House in Round Hill Wine Country! is located just 25 miles from both the Dulles Expo Conference Center and Manassas National Battlefield Park, offering a peaceful escape in the heart of Virginia wine country. The property consistently receives excellent ratings for cleanliness, location, and overall experience.
This four-bedroom home spans 2200 square feet and comfortably accommodates up to eight guests. Amenities include a fully equipped kitchen, air conditioning, a garden, a spa, free Wi-Fi, and parking, providing everything you need for a relaxing and enjoyable stay.

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.

The Salamander Resort and Spa is located in Middleburg, Virginia, just a short drive from Washington Dulles Airport and surrounded by the charming countryside. The resort consistently receives excellent ratings for its location, cleanliness, and overall experience.
The Salamander Resort offers a variety of rooms and suites. Guests can enjoy amenities such as a swimming pool, spa, fitness center, restaurant, bar, and tennis court, as well as activities like horse riding and cycling.

Saddle Tree Loft is an airy apartment situated above a barn in Loudoun County. It offers scenic views of pastures, a pond, woods, and rolling hills. The apartment has received excellent ratings for its location, cleanliness, and user experience.
The apartment has one bedroom, one bathroom, and a guest capacity of two. It features a king-sized bed, a cozy atmosphere with hidden lights and a propane fire pit, and a private entrance with views of the countryside. Guests can also enjoy air conditioning, a garden, parking, and proximity to horse events, gravel roads for biking, wineries, breweries, and distilleries.

This tranquil A-frame guest house is located in The Plains, Virginia, within the heart of Horse Country, offering convenient access to local equestrian attractions.
The two-bedroom, two-bathroom property sleeps up to six guests, features a fully equipped kitchen with appliances including a dishwasher and washer/dryer, and includes a comfortable living room with a fireplace; a larger main house is available for rent to increase capacity.

This three-bedroom house in Leesburg is located a short drive from Stone Tower Winery and Quattro Goomba's Winery, and near the Audubon Naturalist Society Rust Nature Sanctuary and Bull Run Mountains State Natural Area.
This Leesburg abode accommodates up to seven guests, featuring three bedrooms with a king, queen, and twin bed, three bathrooms, and includes air conditioning and heating for year-round comfort.

Villa Maud is located in Purcellville, Virginia, just a short drive from Chantilly, Winchester, Frederick, and Charles Town, offering a peaceful escape from the city while still being close to attractions. This house has received very good user ratings, and excellent ratings for location and cleanliness.
This one-bedroom house features a kitchen with a fridge and microwave, air conditioning, a swimming pool, a hot tub, a terrace or balcony, a garden, a spa, concierge service, room service, and parking. You can also enjoy free Wi-Fi and relax in the hot tub after a day of exploring the area.

This Marshall, Virginia vacation home is located in the rural mountains, a 13-minute drive from Barrel Oak Winery and 19 minutes from Delaplane Cellars.
This 720-square-foot house features two bedrooms, two bathrooms, sleeps four, and includes a fully equipped kitchen, laundry facilities, Wi-Fi, and air conditioning; nearby attractions include the National Sporting Library and Museum.

This charming house is located in the countryside near Upperville, just minutes from Middleburg and wineries, offering stunning views of fields, horses, and the Blue Ridge Mountains. The house has received excellent ratings for its location, cleanliness, and overall experience. This comfortable home features two bedrooms, one bathroom, and a separate garage apartment, accommodating up to six guests. Enjoy a fully equipped kitchen, air conditioning, a private garden, parking, and the option for personalized services like pre-stocked groceries and prepared meals.

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.

Bellwether Farm, a three-bedroom vacation rental near Upperville, Virginia, offers convenient access to the Upperville Horse Show grounds and is surrounded by historic estates, vineyards, and horse farms.
This Middleburg-area house sleeps six, features a chef's kitchen with microwave and dishwasher, air conditioning, a garden, parking, and internet access; guests can enjoy the expansive grounds and the property's rustic-modern ambiance.