Vacation rentals in Upperville

Retreat to horse country!

Enjoy your visit while staying in a private country setting complete with a swimming pool and gardens creating a resort like feel. This beautiful family farm includes an English style apartment with large windows, gas fireplace, 1.5 bathrooms, 1 large bedroom with king size bed. An open concept living space, access to the pool a large & outdoor seating and dinning. Minutes to vineyards, Salamander, Goodstone, Upperville and Shadow Creek in Purcellville! Please read “other details” for pet info😊

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

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.

Garden Oasis outdoor entertainment at FrogPointe.

Nestled in between The Plains and Middleburg, this charming cottage is ready to help you relax. Perfect for family and friends during horse events nearby, like Gold Cup, Middleburg Film Festival, Christmas in Middleburg, Twighlight Polo, and much more. Fully functional kitchen with all you could need to cook a meal, fully furnished, indoor and outdoor dining, two large modern bathrooms, and internet / movies for a calm night in. Please be mindful this property is near a train track, charming!

Reynard's Retreat in Upperville

The perfect hunt box in Upperville and central to all things horses, hunting and wine country. 3BR 2BA home on a country road in the village of Upperville within an hour to DC and only a half mile to Upperville Colt & Horse Showgrounds. Great Meadows, home to horse shows, steeplechase races, and polo…only minutes away. For our non-horsey friends, the house sits is the center of Northern Virginia’s wine country, surrounded by multiple of the region’s best-known vineyards and Sky Meadows.

Fox Hill Barn Guest Cottage Retreat

Enjoy the lovely setting of this romantic spot in nature, just minutes from the historic charm of Middleburg. Set on a tranquil horse property, this cottage offers a serene retreat amidst rolling pastures and breathtaking views. Whether you're a nature enthusiast, equestrian, remote worker, or seeking a romantic getaway, this is your ideal destination. Enjoy nearby wineries, breweries, scenic trails, and the delightful town of Middleburg—only 3 minutes away. Life is too short. Enjoy!

Upperville Hunt Country Cottage

The home has a standing seam metal roof, clapboard-style siding, a stone foundation, a cozy front porch, and second-floor dormer windows. The interior is painted with warm colors and accented by antique oak barn wood paneling and trim in the family room. The flooring is the original antique heart pine. The cottage is decorated as a traditional English Hunt Box, with equine art and memorabilia, lovely antiques, warm carpets on the heart pine floors, and high-end bed linens.

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 Country Getaway in the Heart of Upperville

Located in the center of the historic village of Upperville - across from the Hunter's Head Tavern. House is situated on 2.5 acres of beautiful gardens. It feels like an English cottage that dates back to early 1900s and is newly updated. Tall ceilings with tons of light make this house feel very spacious. There are 2 large bedrooms with 3 beds. Upstairs is a large loft with desk area. Parking provides space for 5 vehicles. Dogs are welcome! Wifi available.

The Studio

🐞1 mile from the center of Middleburg, this gem allows you to enjoy the beauty of a gorgeous Middleburg Farm when you stay in this unique tractor barn turned high end luxury studio apartment! This is for the customer who wants to experience country living but does not want to give up any luxury 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property.

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

Green Acre - A Hunt Country Retreat

Charming 2100 sq ft cottage on 1 acre. Fully fenced for dogs when the gate is closed. Walk to Hunters Head tavern, historic Trinity Church. Close to Lost Mountain winery, Sky Meadows State Park, Ashby Inn. Scenic 10 minute drive to the shops and sights of Middleburg and the Salamander Resort. 15 minutes to restaurants and shops of Marshall. AMENITIES: Full Kitchen *Nespresso * Gas Fireplace *Daybed in Alcove *Wi-Fi *cellular signal extender