Villa holiday rentals in Charlottesville

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.*

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.

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!

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!

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.

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.

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.