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.