Villa vacation rentals in Shenandoah Valley

5 out of 5 average rating, 53 reviews

Villa in Orange

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.*

5 out of 5 average rating, 27 reviews

The exterior of the villa showcases a classic brick façade with large windows, flanked by manicured bushes. A paved driveway leads to a two-car garage, while a welcoming front door is accented by a decorative glass feature. The private backyard is enclosed by a white vinyl fence.

Villa in Manassas

Magic Hide Aways

Experience our villa ✨WHERE COMFORT MEETS STYLE✨ in Manassas! Welcome to our luxurious Magic Hide Aways 🏠✨ with 5 Rooms to sleep in, (4 bedrooms and 1 Office-Sofa Bed), 2.5 bathrooms, gorgeous outdoor Fire place, Patio, and a large parking (5 cars) with a basketball playground. - There's a beautiful décor with plenty of space for your family to relax, creating a warm and festive atmosphere perfect for holiday getaways with a TV in every room! - This house also has a dedicated workplace area.

4.98 out of 5 average rating, 61 reviews

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

Art Deco Villa - Richmond near Carytown and VCU

Art Deco Villa Near Carytown & VCU – Museum District Gem! Stay in our stylish Art Deco Villa, perfectly located in Richmond’s Museum District! Walk to Carytown, VCU, top restaurants, parks, and 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 Book now and experience the best of Richmond!

Villa in Wintergreen Resort

4.96 out of 5 average rating, 76 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!

4.96 out of 5 average rating, 74 reviews

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

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!

Villa in Paeonian Springs

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.

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!

4.9 out of 5 average rating, 39 reviews

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

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.

4.61 out of 5 average rating, 18 reviews

A bubbling hot tub is illuminated by soft blue lights, inviting relaxation. In the background, a striped hammock hangs between two wooden posts, under warm string lights that enhance the cozy outdoor ambiance. Nearby windows softly glow, suggesting an inviting space.

Villa in Shenandoah

Secluded Villa in Shenandoah hot tub+Pool tbl+Wifi

Escape to this secluded charming Villa, just minutes from Massanutten Resort, Skyline Drive, and the scenic river for tubing and kayaking. Nestled on six private acres, this spacious 4-bedroom, 4-bathroom home offers an open-concept layout perfect for the family. Enjoy cozy evenings by the fireplace, challenge friends to a game of pool, or relax by the fire pit under the stars. With modern amenities, WiFi, and plenty of space, it's the ultimate destination for both relaxation and adventure.

5 out of 5 average rating, 153 reviews

A charming two-story white house is framed by tall trees and a colorful sunset sky. Large windows with black shutters create a welcoming appearance, while a front porch with decorative railings invites relaxation. The landscaped garden features vibrant flowers and modern outdoor lighting.

Villa in Shenandoah

Sleeps 7: Hot Tub, Game Room, Fire Pit, BBQ & Pets

Experience the charm of this Shenandoah retreat, complete with a hot tub, pizza oven, and fire pit in a stunning fenced backyard oasis. Perfectly situated near Shenandoah National Park for premier hiking and river activities. This cozy, modern home includes a fully-equipped kitchen and 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!

4.74 out of 5 average rating, 66 reviews

An aerial view of a charming waterfront house is depicted, surrounded by lush greenery. The home features a spacious grassy area, a large screened-in porch, and a deck with multiple levels. A patio area is visible beside the house, enhancing the outdoor living space.

Villa in Manassas

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!

4.98 out of 5 average rating, 124 reviews

A private cinema setting is showcased with a large projection screen displaying an animated scene. Two plush, reclining chairs with built-in cup holders are positioned for comfort in front of the screen, surrounded by soft blue ambient lighting. The room features dark walls, enhancing the cinematic experience.

Villa in Forest

CINEMA★Master Suite★3 KING Beds★XBOX/S★Gym

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!