Vacation rentals in Upperville

Middleburg/Upperville-Stunning,renovated cottage

The Atoka House,a stunning 1801 log home on the historic register in Virginia hunt country.This 2-bedroom, 2.5 bath home with both upstairs and downstairs living rooms,is only 4 miles from Middleburg.Relax in the coziness of the log cabin, catch the spectacular sunsets from the deck and large fenced yard. Gas grill and outdoor firepit. Fireplace may only be used with a duraflame log(provided) for the safety of this historic home. Minutes from wineries, great meadow, polo and Upperville (UCHS)

The Blacksmith Cottage

Just 1 Mile from Historic Middleburg, VA! 🐄✨ Step back in time at our cozy 1900s blacksmith’s cottage—fully renovated with modern comforts but still full of old-world charm! This one-room hideaway is perfect for relaxing, unwinding, and soaking in the countryside. Roam our 66-acre farm and say hello to our mini-Highland cows, rare Kerry Hill sheep, and the cutest mini donkeys you’ll ever meet. 🐑💛🐴 Please note: We’re strictly an Airbnb—no weddings, big parties, or events. No smoking allowed.

The Love Nest

The Love Nest overlooks the Shenandoah Valley and perches on 12 acres surrounded by thousands of acres on all sides including the Thompsons Wildlife Reserve & Appalachian Trail. Wake up watching a beautiful sunrise while sipping coffee from your porch with glorious mountain views. The Love Nest is a great place to rest, relax, and recharge in a quiet, tranquil setting. Located just 3 miles off Rt. 66, it is centrally located near wineries, hiking, sightseeing, events, restaurants, and more!

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!

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.

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.

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.