Holiday houses in Middleburg

English Cottage

MIDDLEBURG ADDRESS. Best country/Middleburg location. Five (+/-) min to town, restaurants, shopping, wedding venues. Centrally located to vineyards, breweries, horse events, more.. Guests 'LOVE' this CLEAN, tasteful, charming/Old English style - private cottage.' Bdrm w/2 twin or together as king bed. (Can separate beds.) Bath w/ rain shower. Kitchenette appointed with modern appliances. Stainless refrig., micro, toaster oven & Keurig. Dogs not left alone. 3 night min during major events.

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.

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.

Self-contained apartment on Organic vegetable farm

Enjoy a relaxing retreat at a genuine sustainable organic vegetable farm. This self-contained apartment is the perfect location for a family get away, or overnight stay whilst visiting the many local wineries and breweries. The farm is located just 5 miles from historic Middleburg, right in the middle of hunt country. See what life is like on a working farm, with seasonal healthy vegetables growing just steps from the door and farm animals grazing outside your window.

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!

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

Patent 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.

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.