Villa vacation 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.

0 of 0 items showing

1 of 3 pages

Guest favorite

The historic Boxwood Villa is framed by lush greenery, showcasing its elegant façade. A welcoming front porch with white pillars leads to the entrance, while well-maintained grounds extend gracefully in front, inviting guests to explore the serene outdoor space.

Villa in Orange

5 out of 5 average rating, 53 reviews

Luxurious Stay for 2 at Historic Estate

Nestled on 13.6 acres of exquisitely landscaped gardens & grounds, Boxwood Villa (circa 1891) is a hidden gem for a couple’s retreat. Named for its stunning boxwood bushes encircling the property, this historic home was thoughtfully renovated by Leslie Gregg, the founder of The Market at Grelen. Her keen eye for contemporary comfort & preservation of historic design breathes new life into this historic manor. *Please note we only accept bookings for couples 30 days out from the requested dates.*

Guest favorite

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, 71 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

Guest favorite

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

4.95 out of 5 average rating, 100 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!

Guest favorite

A large Ginkgo tree stands majestically on a lawn covered in golden leaves, illuminated by warm sunlight. The horizon features silhouettes of distant trees, and the scene captures the essence of a serene autumn landscape.

Villa in Gordonsville

4.95 out of 5 average rating, 84 reviews

Restored Historic Stone Greenhouse

Romance, nature and unique architecture come alive here. This completely restored stone guest home is perched near the top of a ridge on the 1st mountain range west of the Atlantic. With a wall of windows to enjoy the spectacular views to the east, south and west, the Green House is a special experience unto itself. The interior features magnificent, ancient stone walls, flying wooden beams, live-edge wood counters with natural carvings. a leaded glass door and more. Free Raspberry picking!

Superhost

A cozy sleeping area features a spacious bed adorned with neutral-toned linens. Soft natural light filters through white curtains at the window, illuminating wooden walls. A comfortable chair and a small table are positioned beside the bed, while a plush area rug adds warmth to the floor.

Villa in Paeonian Springs

4.94 out of 5 average rating, 49 reviews

The Castle Room, Private Escape Near Leesburg

This property is perfect for a romantic escape in Loudoun. Nestled right off of Route 9 this unique space is only 10 minutes from downtown Leesburg, walking distance to the W&OD trail, and a short drive to all the areas best attractions, restaurants, wineries, and breweries. A tall courtyard fence adds complete privacy where outdoor showers and sunbathing can be done with no interruption. Beautifully decorated room, large shower inside room with comfortable king size bed. Sure to impress!

Top guest favorite

An outdoor patio is arranged with eight red Adirondack chairs surrounding a central fire pit, creating a cozy gathering space. A gazebo with soft lighting is visible, adjacent to a BBQ grill and outdoor dining table set. The backdrop features a modern home, complemented by a warm sunset.

Villa in Shenandoah

5 out of 5 average rating, 168 reviews

Hot Tub, Game Room, Pizza Oven, Fire Pit, Pets

Perfectly situated near Shenandoah National Park for premier hiking and river activities, experience the charm of this Shenandoah retreat, complete with a hot tub, pizza oven, and fire pit in a stunning fenced backyard oasis. This cozy, modern home includes a fully-equipped kitchen and 3 comfortable bedrooms ideal for families and groups; pets are welcome! Enjoy local vineyards, diverse dining options, and vibrant festivals. Embrace your ultimate getaway close to nature's beauty. Book today!

Guest favorite

The modern multi-level home is surrounded by lush greenery, featuring large windows that allow for natural light. A spacious deck extends from the lower level, providing outdoor living space. The unique architectural design includes a circular area, enhancing the property’s distinctive appearance.

Villa in Bentonville

4.9 out of 5 average rating, 40 reviews

Chateau Solace: Seclusion, Hot Tub, River

Chateau Solace is a hidden gem nestled on 10 private acres only 90 mins from Washington DC. Surrounded 360 by GW National Forest, our serene home offers an unparalleled experience with a hot tub, steps from hiking trails and river adventures, and all the Shenandoah Valley has to offer. This treetop delight allows you to immerse yourself in the tranquility of nature while enjoying modern comforts like high speed internet & a home designed for ease & relaxation without another house for miles.

Top guest favorite

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, 81 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.

Superhost

A modern kitchen is highlighted by sleek white cabinetry and dark granite countertops. Stainless steel appliances, including a refrigerator and oven, are integrated into the design. A small bar area features two red stools, contributing to the high-tech and functional layout.

Villa in Glen Allen

4.81 out of 5 average rating, 26 reviews

The Deluxe Oasis in the west end of Richmond

Located in the heart of west Henrico County, this secluded 4000sf European style trendy home features a high tech kitchen with its countless fine utensils and condiments. Parties not allowed. 3 bedrooms and 1 office provide 3 queen beds, 1 twin futon. Master bedroom and bathroom not available since occupied by owner. The neighborhood is quiet and there's plenty of parking off street, less than 0.5 mile to shopping clusters on Staples Mill Road between Hungary Road and E. Parham Road.

Guest favorite

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

4.77 out of 5 average rating, 73 reviews

Entire Lakehouse property / Private DOCK (DC/DMV )

Perfect for WORK AND/OR PLAY !! Amazing waterfront property. Tranquility meets convenience of 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 around deck!

Guest favorite

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, 134 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 favorite

An indoor saltwater pool area features a large, tranquil pool surrounded by multiple windows allowing natural light. Lounge chairs line one side, with red and white striped towels neatly arranged. The ceiling is accented with skylights, enhancing the spacious feel.

Villa in Luray

4.96 out of 5 average rating, 89 reviews

Private Indoor Pool~WiFi~ Arcade~Fire Pit~Views

Enjoy a beautiful spring escape! The villa features spacious and tastefully decorated interiors, providing ample space for relaxation and enjoyment. With its huge 20ft by 40ft heated up to 84 degrees indoor salt water pool you and your family can indulge in refreshing swims and soak up the sun in complete privacy. Whether you're seeking a rejuvenating getaway or quality time with your friends our villa rental is the perfect choice for a memorable and enjoyable vacation.