Villa vacation rentals in Charlottesville

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Top-rated villa rentals in Charlottesville

Guests agree: these villas are highly rated for location, cleanliness, and more.

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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.*

LocationFamilyQuiet

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

4.96 out of 5 average rating, 25 reviews

Classic Estate by Montpelier+Charlottesville+Wine

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.

LocationFamilyOutdoor spaces

Top 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

4.96 out of 5 average rating, 146 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!

FamilyValueAmenities

Top guest favorite

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.

Private room in Dyke

4.99 out of 5 average rating, 176 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.

FamilyValueWifi

Top guest favorite

Private room in Dyke

4.93 out of 5 average rating, 114 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.

FamilyLocationNearby

Superhost

Villa in Shenandoah

4.98 out of 5 average rating, 195 reviews

Pizza Oven • Hot Tub • Game Room • Pet Friendly

Your Private Escape & Backyard Pizzeria Welcome to Time to Chill Shenandoah, where small-town quiet meets big-mountain adventure. While we are a strategic launchpad for Shenandoah National Park and Massanutten Resort, we’ve designed the property so the best part of your trip happens right here in your own private, fenced-in sanctuary!

LocationFamilyPool

An open living area is showcased, featuring a bright kitchen with white cabinetry and a dining table surrounded by wooden chairs. A comfortable sofa and a small side table are present, with natural light entering through the windows on two sides.

Villa in Crozet

Chapter 2 Mountain Living

1 bedroom apartment that is ideal for long term stays, month to month. Full kitchen, Wi-Fi, open living area with its own entrance. The unit is well suited for traveling nurses, college students and professors.