Villa vacation rentals in Woodstock

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Top-rated villa rentals in Woodstock

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Superhost

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.*

Top guest favorite

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

4.95 out of 5 average rating, 22 reviews

Luxurious, Pet-Friendly Flower Farm by 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 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

4.96 out of 5 average rating, 75 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!

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, 39 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.

Superhost

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

4.58 out of 5 average rating, 19 reviews

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.

Guest favorite

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

5 out of 5 average rating, 154 reviews

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

Top guest favorite

Villa in Harpers Ferry

4.99 out of 5 average rating, 72 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.

The villa is set amidst lush greenery, featuring a spacious gravel driveway leading to the grand entrance. The two-story structure showcases a charming mix of yellow and green hues, complemented by well-manicured landscaping and trees that provide natural shade.

Villa in Hume

4.52 out of 5 average rating, 31 reviews

Historic Virginia Wine Country Villa w/ Pool, Yard

A unique adventure begins at this villa in Hume! The original part of the home, 'Barbee's Tavern,' was built before the Civil War and was used as headquarters for the Union and Confederate armies. Today, it's a vacation rental equipped with modern luxuries like a seasonal saltwater pool. The villa has 6 king beds, 6 full baths, 2 half baths, and additional sleeping accommodations. The property is also neater local vineyards like Winding Road Cellars and Philip Carter Winery of Virginia!

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

4.95 out of 5 average rating, 58 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 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.

Guest favorite

A charming villa is nestled among lush greenery, with large windows reflecting the surrounding landscape. A gentle flow of water can be seen in the foreground, and the property is framed by vibrant trees, suggesting a peaceful and scenic environment.

Private room in Dyke

4.89 out of 5 average rating, 126 reviews

Rm202SingingSprings, (WaterfrontHotTubPrivSetting)

If you are looking for lodging nestled amongst the beautiful Shenandoah Mountains a few doors from the Blue Ridge School for boys in St. George, VA. Singing Springs offers the peace and tranquility you are searching for in a "Bed 'n Nightcap". From the gently flowing waters of the river that flows through it, to the majestic mountain peaks that surround you, this Villa will settle your soul.