Villa holiday 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.*

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.

Historic Estate with Enchanting Gardens

Nestled on 13.6 acres of beautifully landscaped gardens and grounds, Boxwood Villa exudes an old-world charm that will transport you to a bygone era of elegance and sophistication. This garden wedding venue and historic lodging property is named after the stunning boxwood bushes that encircle it, creating a magical and romantic atmosphere. One of the most homes in Virginia, Boxwood Villa was originally built in 1891 and is located just outside the town of Orange, Virginia. Sleeps 10; 5 bedrooms

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!

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.

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.

The Villa @ Skybridge

“Skybridge” is a huge and private home on a seven-acre property ideally situated just a few minutes outside Purcellville in rural Loudoun County. Less than an hour outside D.C., it provides easy access to local wineries, breweries, child-friendly farms, the Appalachian Trail, historic Purcellville, and Middleburg, VA. It comes stocked with all you need, and guests have access to a pool (in season), hot tub, fire pit, built-in charcoal grills, and more.

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. Autumn has just begun and the vineyards are open! Dining and shopping in nearby Orlean, Front Royal, and Flint Hill. Peaceful and mountainous horse country to get away, outside and unwind for a while. Conveniently located off Route 66.

Perfect getaway at a Waterfront Lake Villa

Bring the whole family to this great place with lots of room for fun and a big lake to enjoy. The house is suitable for big or small groups. Stunning sunsets throughout the year. During cold season, we have a fire pit outside looking a the water. There’s also a great trampoline outside for kids to enjoy and a nearby beach to play in the sand. Enjoy the lake views and the peace!

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.