Holiday houses in The Plains

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Top-rated holiday rentals in The Plains

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Guest favourite
The cabin exterior features a blend of rustic log construction and large windows that invite natural light. Surrounded by lush greenery, the spacious deck extends outdoors, adorned with potted plants and a well-manicured lawn, providing a serene outdoor space.
Cabin in Haymarket
4.94 out of 5 average rating, 271 reviews

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

Top Guest favourite
A quaint cottage is nestled among manicured gardens and trees. The exterior features a simple white facade, a sloped metal roof, and a large front door, all framed by lush greenery and shrubbery. Natural light gently highlights the surroundings.
Cottage in The Plains
4.98 out of 5 average rating, 236 reviews

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!

Top Guest favourite
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guesthouse in Middleburg
5 out of 5 average rating, 119 reviews

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.

Guest favourite
A covered outdoor patio is visible, featuring two wicker chairs with cushions and surrounded by planter boxes filled with flowers. A view of well-maintained greenery and a gravel area highlights the peaceful outdoor setting.
Cottage in Marshall
4.9 out of 5 average rating, 124 reviews

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!

Top Guest favourite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
4.99 out of 5 average rating, 282 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Top Guest favourite
A spacious bedroom features a queen-size bed adorned with decorative pillows. Natural light enters through a skylight and windows. A television is positioned against a wall, accompanied by a combination of vintage and modern furniture pieces, creating a cozy and inviting atmosphere.
Apartment in The Plains
4.98 out of 5 average rating, 672 reviews

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.

Guest favourite
Apartment in Gainesville
4.92 out of 5 average rating, 106 reviews

Cozy 2 bedroom, 2 bath apartment/Basement

This walkout Basement/Apartment in Gainesville, VA. Easy excess to Route 66 and 29. It has 2 bedrooms 2 full bathroom . The master bedroom has an attached bathroom. The kitchenette comes with a microwave, k cup coffee maker, Hot water kettle,toaster,Refrigerator, Washer and Dryer. The living room has a smart TV, The accommodation has its own private entrance from the back of the house. Our family lives upstairs. Jiffy Lube: 2mi IAD: 25 mi D.C: 37 mi Free street parking available.

Top Guest favourite
Farm stay in Aldie
4.97 out of 5 average rating, 118 reviews

Charming Cottage On Horse Farm Middleburg Area

The cottage is set on a beautiful private farm in the center of historic Aldie, Va. and 5 minutes to historic Middleburg. The cottage is surrounded by 11.11 privately fenced acres and is in a very cute setting with a shower and bathroom downstairs along with a kitchen and bedroom upstairs with one queen bed. The apartment accommodates 2 easily with table and chairs inside and on the porch for your comfort. Great opportunity to experience and relax on a small farm in hunt country.

Top Guest favourite
A weathered wooden fence is presented in the foreground, supporting a round sign that reads 'The SOPER House, Est. 1964.' The backdrop features a cluster of trees with autumn leaves, and the cottage can be seen softly illuminated in the distance.
Cottage in Warrenton
4.96 out of 5 average rating, 361 reviews

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.

Top Guest favourite
A bright living area is filled with natural light from two windows, featuring a comfortable dark sofa with plaid throw pillows. A simple media console supports a television, and various indoor plants add greenery. A coffee table displays a wooden chess set and board games.
Guest suite in The Plains
5 out of 5 average rating, 162 reviews

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.

Top Guest favourite
A modern cabin is nestled among trees, featuring a sleek design with large windows that allow light to emanate from within. The surrounding rocky terrain is softly illuminated by exterior lighting, creating a calm ambiance in the early evening fog.
Holiday home in Front Royal
4.99 out of 5 average rating, 414 reviews

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.

Top Guest favourite
A charming cottage is surrounded by lush greenery, featuring a simple front porch with seating. The gravel path leads to a well-maintained garden with assorted plants and bushes, providing an inviting entrance under the shade of a mature tree.
Home in Middleburg
4.99 out of 5 average rating, 204 reviews

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

  1. Airbnb
  2. United States
  3. Virginia
  4. Fauquier County
  5. The Plains