Vacation rentals in Upperville

Spectacular View, PET FREE, Skylight and Hot Tub

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry, quiet peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

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.

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.

Quaint cottage in historical town of Paris VA!

Welcome to my home! This house was built in the 1820’s in the historical town of Paris, Virginia! With lots of history and character this house still has some of the original exposed beams and hardwood flooring! If you enjoy the outdoors, wineries, breweries, and shopping this is a perfect location for your stay! Minutes from the Appalachian trail, and Sky Meadows park there’s plenty of hiking around. Famous Ashby Inn restaurant just a short walk away and many more amazing places!

WILD HARE COTTAGE king bed

Perfect for exploring wine country we are 10 minutes from Bluemont Station and Dirt Farm Brewing This property has two bedrooms King and Queen beautiful bathroom in the middle. The kitchen perfectly sized to gather four people. large sitting room out front. Sit on the front porch and watch the travelers pass by on the gravel road. Walk up to the historic Philomont store. Please note this cottage is attached to the front of the main house it’s completely separate utilites and all

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.

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.

The Cottage at Stonecroft

Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

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.

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.