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Villa holiday rentals in Shenandoah Valley

Find and book unique villas on Airbnb

Top-rated villa rentals in Shenandoah Valley

Guests agree: these villas are highly rated for location, cleanliness and more.

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Guest favourite
Villa in Leesburg
4.92 out of 5 average rating, 156 reviews

Luxury Private Estate with 6 Bedrooms in Leesburg

luxury Private Estate in Leesburg. Perfect for family fun near wineries & breweries! with 6Bedrooms, huge owners suite & lux bath w/heated floors, soaking tub. The primary suite has a private living room that leads to a balcony. Huge open kitchen with high-end appliances, double wall-oven, oversized island, granite counters, skylights, heated floors, new sunroom, Bluetooth ceiling speakers. Covered Porch with Brand New Hot Tub. Beautiful outdoors with firepit under the stars. Welcome to Harmony.

Top guest favourite
The exterior of a large white house is presented, featuring multiple gabled roofs and a welcoming red front door. Large windows allow natural light to fill the interior, while a neatly maintained green lawn enhances the home's curb appeal.
Villa in Haymarket
4.99 out of 5 average rating, 101 reviews

The Mulberry Manor House

The Mulberry Manor House is conveniently located outside of Washington DC, close to Dulles International & Reagan International airports. Minutes from I66 & public transportation to DC. In the heart of Horse & Wine Country, close to Manassas National Battlefield Park, in historic Haymarket, minutes from historic Middleburg, & The Plains, & still in close proximity to high end shopping, restaurants, movie theaters, hospitals & all the major modern conveniences that Northern Virgina has to offer.

Guest favourite
A charming two-story brick house is surrounded by lush green landscaping. The home features white shutters and a welcoming front porch. Large windows allow natural light to fill the interior, while the manicured lawn enhances the overall inviting appearance.
Villa in Somerset
4.96 out of 5 average rating, 24 reviews

Luxurious Farm Near C'Ville+Montpellier+Wineries

A fully renovated gem with eat-in kitchen, quartz countertops + new appliances. High-speed FiberOptic! 1st Floor: Half bath, living room, fireplace, sunroom. Upstairs: 3 bedrooms, 2 baths, clawfoot tub + shower, walk-in shower suite. Sunsets to the front, sunrises to the back. Perfect crocket lawns. Fenced yard for Fido! Cut flowers+Veggie gardens, sounds of crickets, occasional trains (surprisingly exciting!), within minutes of historic sites + wineries. You'll enjoy your stay at Maple Crest.

Top guest favourite
A comfortable living area features a light gray sectional sofa and a glass coffee table. Natural light enters through the window, illuminating the space. A television stands on a wooden cabinet, and a decorative plant adds a touch of greenery.
Villa in Richmond
4.96 out of 5 average rating, 85 reviews

Classic Richmond Retreat - Carytown-Downtown-VCU

Classic Richmond Retreat- Steps from authentic neighborhood restaurants, coffee houses and culture! Stay in this stylish Art Deco style Villa, perfectly located in Richmond’s Museum District! Walk to Carytown, VCU, top restaurants, parks & museums. ✔ Experience the 4 Cs - Cozy, Comfortable, Clean, & Convenient ✔ Prime Location – Steps from downtown attractions ✔ Modern Amenities for a hassle-free stay ✔ Private fenced backyard w/ dining area and porch swing -Off Street Parking

Top guest favourite
A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.
Villa in Wintergreen Resort
4.96 out of 5 average rating, 137 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

Superhost
The home features a single-story brick facade with green shutters on multiple windows. A gently sloping lawn leads to the entrance, surrounded by landscaped greenery. Tall trees form a backdrop, enhancing the peaceful wooded setting.
Villa in Manassas
4.8 out of 5 average rating, 148 reviews

Huge Private Wooded Estate 5BR/3BA in Manassas, VA

Welcome to this beautiful 2 level single-family private wooded getaway, located in historic district Manassas off Virginia State Route 234. This lovely retreat sits on 2 acres of land, has been renovated inside and out with our guests in mind. Three bedrooms/Two bathrooms on main level and huge finished basement to comfortably sleep 10. Fully equipped kitchen, in-home office, gym, washer and dryer. If you are in town for business or pleasure, this home is everything you will need for your stay.

Top guest favourite
A serene lagoon is depicted, with two individuals quietly floating in the calm water, surrounded by lush greenery and rocky cliffs. The surface mirrors the tranquil sky, while the soft colors of the setting sun enhance the peaceful atmosphere.
Villa in Harpers Ferry
4.99 out of 5 average rating, 85 reviews

Amazing Lagoon, Beach, Cross Fit Gym, Fishing

This the definition of "Wild and Wonderful West Virginia! magical place, a former rock quarry now lagoon. There is no public access to this property. The only access to the Lagoon, Beach and other amenities is via booking or owners explicit permission. This is a complete unit that is on its own level, own access, own parking, own amenities, Owners live on upper level with fully separate entrance, parking, access, etc. No shared internal spaces. Double sound insulation, no noise worries.

Top guest favourite
A cozy living room features a light-colored sofa adorned with decorative cushions, complemented by a round glass coffee table. A green accent chair is positioned opposite the sofa. Natural light is softly filtered through sheer curtains, with a vibrant plant adding a touch of greenery.
Villa in Herndon
5 out of 5 average rating, 21 reviews

Dulles Executive Retreat | 1BR + Office | Near IAD

✨ Welcome to Dulles Executive Resort, an elegant retreat designed for business travelers, extended stays, and guests seeking comfort near Washington Dulles International Airport (IAD). Private 1BR with an executive office and half-bath, ideal for work trips or couples celebrating special moments. Sleeps up to 4 with a premium sleeper sofa. Enjoy high-speed Wi-Fi, a marble kitchenette, a spa-style bath, a private entrance, parking, and a peaceful patio minutes from Reston Town Center.

Guest favourite
A serene view of a landscaped backyard leads to a calm lake, framed by vibrant green trees and blooming azaleas. A wooden deck with a pergola offers an inviting outdoor space, perfect for relaxation and enjoying the surrounding nature.
Villa in Manassas
4.79 out of 5 average rating, 82 reviews

Entire Lakehouse property / Private DOCK (DC/DMV )

Perfect for WORK AND/OR PLAY !! WATERFRONT property. Tranquility AND Convenience ! Major Business hubs, DC metro area!Secluded w Phenomenal View from every corner! Ideal setting for vacation too ! !This gorgeous Lake house comes w a private Dock ready for your excursion! 4 Bedrooms furnished w sleeper on lower level (or 5th bedroom). NEW updates & furnishings ! Great amenities incl kayaks & pedal boat complimentary or simply just enjoy the amazing sunset from the wrapped ar

Top guest favourite
A cozy entertainment area features a large projection screen displaying a movie scene. A stylish coffee table sits in front, equipped with mugs and a kettle, complemented by soft lighting along the wall that adds to the inviting ambiance. A plush area rug adds warmth to the space.
Villa in Forest
4.98 out of 5 average rating, 163 reviews

Luxe Cinema Master Suite + 3 KING Beds + Extras

Your private CINE-PLEX! Club Gym, FIVE Amazon Fire TVs, 3 KING beds, Master Suite, 110in screen, 3-tier seating, smart lighting in every room, whole-home audio, XBOX Series S, Alexa! Easy PARKING right at the front door. YouTube Video Tour search Guelzo Experiences. Created for you by a sound designer whose resume includes Fast & Furious 7, Robocop, and more! We love movies and want to share something only a professional’s touch could craft, a multiplex viewing experience!

Guest favourite
An aerial view captures a spacious property surrounded by lush greenery. A private pool is visible in the backyard, complemented by sun loungers. The house features a distinctive shape with a modern roof, nestled comfortably among the trees in a tranquil setting.
Villa in Purcellville
4.89 out of 5 average rating, 27 reviews

The Villa @ Skybridge

“Skybridge” is a huge and private home on a seven-acre property ideally situated just a few minutes outside Purcellville in rural Loudoun County. Less than an hour outside D.C., it provides easy access to local wineries, breweries, child-friendly farms, the Appalachian Trail, historic Purcellville, and Middleburg, VA. It comes stocked with all you need, and guests have access to a pool (in season), hot tub, fire pit, built-in charcoal grills, and more.

Superhost
Villa in Rileyville
New place to stay

Hamatreya- Panoramic Shenandoah Views

Award-winning contemporary retreat on 10 acres with breathtaking mountain vistas. Inspired by Emerson's poetry, this eco-luxury home features three en-suite bedrooms plus studio apartment, expansive stone terrace with outdoor kitchen and fireplace, handcrafted interiors, and seamless indoor-outdoor living. High-speed internet. Featured in three distinguished magazines. Perfect for families or groups seeking an exceptional Shenandoah escape.

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