Villa holiday rentals in Charlottesville

5 out of 5 average rating, 53 reviews

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

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.*

4.96 out of 5 average rating, 24 reviews

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

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.

Villa in Wintergreen Resort

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.

4.95 out of 5 average rating, 106 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!

4.95 out of 5 average rating, 84 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!

5 out of 5 average rating, 173 reviews

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

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!

A spacious two-unit home is set against a backdrop of rolling mountains. The structure is designed with multiple gable roofs and features large front windows, surrounded by landscaped greenery. Two garages are visible, indicating ample parking space for guests.

Villa in Massanutten

Regal Vistas Massanutten Luxury 2BR/2BA

Luxury and comfort! Garages, gated with private gym and pool for Regal Vista guests, BBQ grill on patio/deck, large vaulted ceilings, full kitchen, sleeps 6, closest to water park, quiet. Two units can be combined for entire house (4/4) with two garages. Each unit 2 fireplaces, large floor-to-ceiling windows. 4-Season Resort with skiing, mountain biking, golf, numerous heated indoor pools and outdoor pools (seasonal), gyms, children's activities, hiking, close to Shenandoah National Park.

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.

4.89 out of 5 average rating, 131 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.

The villa is situated alongside a gentle river, illuminated warmly from within. Large windows reflect the surrounding natural beauty, with trees framing the scene, showcasing a peaceful retreat nestled in the foothills.

4.99 out of 5 average rating, 162 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.

4.92 out of 5 average rating, 105 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.

The villa is nestled among trees, illuminated warmly from within, creating a cozy ambiance against the backdrop of dusky mountains. A gentle stream flows nearby, reflecting the soft light from the building, while the serene natural surroundings enhance the peaceful setting.