Holiday houses in The Plains

The Cottage on Main -Virginia Wine & Horse Country

The Cottage on Main, originally built around 1840 recently underwent a full renovation! Walk to the restaurants and shops of The Plains or explore the quaint towns of Marshall, Middleburg, Warrenton, Upperville with just a few minutes drive. This one bedroom, 1 bath cottage with full kitchen, living & dining area has everything you need for a weekend getaway or extended stay. The Plains is home to Gold Cup & many other equestrian events, amazing dining & shopping and the Virginia wine country!

Family · Value · Long stay

Lodge on the Lake

A quiet 17 acre, ONE room cabin set on a private small lake, fishing, swimming, and kayaking. Equipped with a full kitchen, a grill, 4 OUT DOOR showers, no showers in cabin. Sleeps 4, 1 QUEEN SIZE BED AND 1 PULL OUT HIDE-ABED. There is a $25/PP per day for extra guests , with prior approval by host. Pet friendly. Cameras are on site. 1 at the parking lot, 1 on the side deck, back deck, covered porch, up stairs open covered card/chest room, 2 on the main dock & water, 1 outside stone patio

Value · Family · Pool

Guest House on Horse Farm -2 bedrooms/2 bath

Take it easy at this unique and tranquil getaway located in The Plains, Virginia - Horse Country. This unique A-Frame design guest house has 2 bedrooms and 2 bathrooms. The master has a king bed with an ensuite bathroom and the upstairs has 2 queen beds and a full bathroom which boasts a shower made out of field stone. The guest house has a full size refrigerator, washer dryer, dishwasher, microwave, counter top burners, large toast-r-oven & microwave. Comfortable living room and fireplace.

Location · Value · Quiet

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, wi-fi, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

Location · Value · Kitchen

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.

Family · Location · Kitchen

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!

Location · Family · Cleanliness

Middleburg Bliss!

Treat yourself to a peaceful getaway in our cozy guest cottage! Nestled on 10 acres of serene, park-like grounds, our private retreat offers peace and tranquility just 10 minutes from charming Middleburg. Enjoy natural beauty and countryside sounds while exploring nearby award-winning wineries, breweries, and historic towns. Enjoy great privacy with us nearby if needed. Whether you’re here to unwind or embark on local adventures, our cottage is the ideal home base for your Middleburg escape.

Value · Location · Parking

Entire 11 Acre MTN Estate & Farm, sleeps 15!

A gorgeous 5000sqft , 2-story, 5 bdrm, mountain cabin style home with a long and spacious porch...Great location for enjoying all the country has to offer. The nearby area is filled with wonderful attractions, including amazing restaurants, wineries-breweries-cideries, historic battlefields and museums, hiking, River adventures, spelunking, National and State Parks, flea markets and antiques, horse shows, polo matches, the historic villages of Middleburg, Aldie, Upperville and The Plains.

Location · Value · Indoor spaces

The Garden House

The Garden House is the perfect place for two couples, or a group of five, to gather in a secluded setting in the center of the village of The Plains. The newly-renovated 19th century farmhouse shares a front garden with a one-bedroom guest house, The Artist's Cottage (listed separately on Airbnb). Excellent restaurants, a coffee shop, and art galleries are just around the corner. The Plains is a center for equestrian events, biking, and vineyards in the Blue Ridge Mountain foothills.

Family · Location · Comfort

The Soper House-A Quaint & Lovely Country Getaway

The Soper House is a 1,000 sq.ft. ranch-style home with 3 bedrooms & 1 bath perfectly situated on a 5 acre farmette. Located in Fauquier County, VA. also known as Hunt, Horse & Wine country, each of the bedrooms uniquely displaying these historical themes. This charming cottage has a fully functional eat-in kitchen, a living room & a mudroom with W/D for your use. There are a few neighbors that are visible & we live in the adjacent property & can be easily available.

Family · Value · Breakfast

Middleburg Wine Country Retreat on 135 Acres

Escape to Virginia Wine & Horse Country at LiveEdge, a newly renovated retreat on a private 135-acre farm just minutes from Middleburg. Surrounded by rolling countryside, wineries, breweries, and renowned equestrian destinations. Enjoy a chef's kitchen, spa-like baths, bright bedrooms with scenic views, and a spacious deck ideal for grilling and unwinding after a day of wine tasting, dining, shopping, or exploring Hunt Country. High-speed fiber internet included.

Family · Location · Comfort

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.

Family · Value · Checkout