Villa vacation rentals in Woodstock

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.*

Family · Location · Sleep quality

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.

Family · Location · Indoor spaces

Chateau Solace: Lux Spa Retreat w/ Hot Tub & Views

Escape to Chateau Solace, a striking architectural Villa on 10 private acres just 90 mins from DC. Bordering the GW National Forest, this secluded retreat offers a private hot tub, direct hiking access, and Shenandoah River proximity. Experience "treetop" living with dramatic glass walls, Starlink WiFi, and modern luxury. A perfect sanctuary designed for deep relaxation with zero neighbors in sight. Come for the architecture, stay for the peace. We are more than a rental we are a feeling.

Family · Location · Decor

Mountain Views • Kayak/Fishing• Game Room

A fairytale-like luxurious villa with jaw dropping views of the Shenandoah river and mountains, situated on a hilltop with its own private vineyard. A perfect retreat surrounded by the Shenandoah wilderness. Bring your family and friends to disconnect from the city life, enjoy outdoor adventures on the river or in the mountains. Watch gorgeous sunsets and witness abundant wildlife without leaving the wraparound screened porch. This place is absolutely magical and rejuvenating

Location · Family · Laundry

Hamatreya- Panoramic Shenandoah Views

Award-winning contemporary retreat on 10 acres with breathtaking mountain vistas. Inspired by Emerson's poetry, this eco-luxury home features three en-suite bedrooms plus studio apartment, expansive stone terrace with outdoor kitchen and fireplace, handcrafted interiors, and seamless indoor-outdoor living. High-speed internet. Featured in three distinguished magazines. Perfect for families or groups seeking an exceptional Shenandoah escape.

Location · Family · Indoor spaces

Hazegrov in Virginia Horse & Wine Country

Private suite with private parking. Property faces 4000 acre wildlife preserve and hiking trails. Entrance to Shenandoah National Park is 5 minute drive away. Dining and shopping in nearby Orlean, Front Royal, and Flint Hill. Peaceful and mountainous horse and wine country to get away, outside and unwind for a while. Conveniently located off Route 66. Extended stays welcome.

Family · Location · Walkability

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.

Location · Family · Hospitality

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.

Value · Location · Outdoor spaces

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!

Family · Value · Sleep quality