
Holiday houses in The Plains
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Top-rated holiday rentals in The Plains
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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!

Timber Creek: Falls - A Shenandoah Cabin
Nestled on 8 acres, the Timber Creek Falls A-frame sits on the Shenandoah National Park border overlooking a beautiful cascading waterfall. A 90-min drive from DC, this cabin getaway will have you unwinding in tranquility. A hot tub offers views stretching 50mi to West Virginia on a clear day, and the closest neighbor is a half mile away. A truly private retreat comes w/ modern conveniences including: EV charger, smart devices, flat-screen TV, standing desk, wood burning stove & spa bathrobes.

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.

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!

John Pope Cabin Browntown Va. We now have Starlink
Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

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.

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.

The Lodge at Turkey Creek
Your low-tech getaway awaits in the heart of the coveted Virginia Piedmont horse & wine country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, quaint towns, idyllic scenery, mountains and wineries. Only 40 min to Shenandoah Nat’l Park & 20 min to Sky Meadows State Park.

Horse farm near Manassas Battlefield.
“Chip and Joanna” style accommodations. Private suite, private entrance (bedroom, bath, kitchenette). Close to: Manassas Battlefield (25 mile trail); Skymeadow State Park (nice trails); Wineries, distilleries, breweries and great restaurants -5 miles; VRE connections - to METRO; 3 miles to Manassas airport. ONLY 6 miles to Jiffy Lube Live. Fire pit and wood. Not accepting pets at this time. Cot and Pack n Play available.

Luxury hunt country getaway!
Charming 1100 sq. ft space in the heart of Hunt Country. Lower level private entrance and parking. Fully outfitted kitchen, Nespresso coffee maker, french press and all the kitchen necessities. Walking distance to coffee shops, restaurants and antique stores. Close to wineries, Great Meadows and popular cycling routes. Convenient location 40 miles just outside of DC, right off route 66 but nestled away in the countryside.

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.

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.
Popular amenities for The Plains holiday rentals
Other great holiday rentals in The Plains

The Hayloft

Designer Modern Mountain Escape (w/View & Hot Tub)

Middleburg Carriage House Studio - The Loft

Horizon | Hot/Cold Tub, Fireplaces, Sauna, EV Plug

The Serenity Cabin | Firepit | Wineries | Hiking

The Garden House

Charming Cottage, Walk to Downtown, Porch Swings

Charming 3BR Farmhouse • Wine Country Getaway
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Shenandoah National Park
- Georgetown University
- Walter E Washington Convention Center
- The White House
- National Mall
- Nationals Park
- District Wharf
- National Museum of Natural History
- Luray Caverns
- Stone Tower Winery
- National Museum of African American History and Culture
- Arlington National Cemetery
- Georgetown Waterfront Park
- Howard University
- Washington Monument
- National Harbor
- The Anthem
- Capital One Arena
- Early Mountain Winery
- Smithsonian American Art Museum
- The Pentagon
- Smithsonian National Zoological Park
- Great Falls Park
- Lincoln Park





