Villa vacation rentals in Charlottesville

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Top-rated villa rentals in Charlottesville

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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

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!

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, 74 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 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

4.61 out of 5 average rating, 18 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, 153 reviews

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!

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.

Top guest favorite

The rear of the villa features multiple deck areas for seating and dining, surrounded by lush greenery and a backdrop of trees. Large windows reflect natural light, while an umbrella provides shade over an outdoor table. Various seating arrangements invite relaxation and outdoor enjoyment.

Private room in Dyke

4.99 out of 5 average rating, 148 reviews

Rm201 SingingSprings (Waterfront,Hottub,PrivBath)

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 as 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.

Top guest favorite

Private room in Dyke

4.92 out of 5 average rating, 91 reviews

Rm101SingingSprings(Waterfront,Hottub,PrivSetting)

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 as 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.

Top guest favorite

The exterior of the villa showcases a spacious deck surrounded by greenery, featuring several sitting areas and an umbrella-covered table. A red umbrella provides a pop of color against the neutral façade, while large windows offer views of the natural landscape.

Private room in Dyke

4.98 out of 5 average rating, 111 reviews

Rm203SingingSprings (Waterfront,HotTub,PrivBath)

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.