Vacation rentals in Middleburg

Modern Home on Middleburg Equestrian Farm

Surprise and delight abound around every corner in this newly renovated, open floor-plan 3 bedroom, 2 bath getaway. Furnished by BoConcept and outfitted with the latest appliances, Gibson House is the ideal getaway for couples or small families looking for a weekend escape with all the comforts of home. Visit with the horses in the adjacent paddocks. Come enjoy wineries, shopping, history, steeplechase racing and polo in Middleburg and the nearby towns of Upperville, The Plains, and Marshall.

Welcome to the Hidden Hive!

The Hidden Hive is located on beautiful, tranquil farmland, within a few minutes of Loudoun County’s premiere wineries and breweries. Rest your head here after a hard day’s hike on the Appalachian Trail or a celebratory evening at a Bluemont wedding. We are a hobby farm and own chickens, goats, dogs, and barn kitties. Wildlife such as deer can be seen, and owls heard here at night. You may see cyclists or horseback riders pass along our historic Civil War roads. We can’t wait to host you!

Rose End

Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Middleburg Carriage House

Hunt Country charm with modern design and amenities. The rebuilt carriage house overlooks adjacent vineyard and Blue Ridge Mountains. The interior showcases reclaimed materials and wood from the original dwelling. The large flagstone patio offers rolling mountain views where you can enjoy your morning coffee or glass of local wine after a day of winery visits. A two minute drive to historic downtown Middleburg; next to wineries and polo. Enjoy your next getaway!

Status House at the Little River Inn

The Patent House is a part of the Little River inn in Aldie, Virginia and we have been in business for 36 years. A full breakfast is included in your stay, we use local meats, eggs and serve everything from French toast, to quiche, to Dutch apple baby. The Patent House is located across the driveway from the Main House where breakfast is served. There is a bedroom with a double bed, a bathroom attached, a living space and a working wood burning fireplace.

Middleburg Historic Country Estate/Farm Stay

8 miles from Upperville Horse Show ! Enjoy all that Virginia horse and wine country have to offer with this conveniently located country retreat. Hike at Sky Meadows, explore, attend polo matches and horse events at Great Meadow and explore the historic charm of Middleburg. The Plains, Marshall and Middleburg are hip foodie towns with amazing farm-to-table restaurants and coffee shops. . Go out or stay home, enjoy your time! !

Luxury hunt country getaway!

Charming 1100 sq. ft space in the heart of Hunt Country. Lower level private entrance and parking. Fully outfitted kitchen, Nespresso coffee maker, french press and all the kitchen necessities. Walking distance to coffee shops, restaurants and antique stores. Close to wineries, Great Meadows and popular cycling routes. Convenient location 40 miles just outside of DC, right off route 66 but nestled away in the countryside.

Littlefield Cottage

If you are looking for a super sweet and charming cottage to escape to, you've come to the right place. Live like a local in our little cottage and find out for yourself all the beauty that can be found in the country sides of Virginia. Comfortably blending modern conveniences with historic charm, the cottage sits just 1 mile outside of the quaint town of Middelburg and next door to Greenhill Winery.