Holiday houses in Greenwood

Farmhouse on Working Vineyard

Situated on the east side of the Blue Ridge, this renovated farmhouse in beautiful Nelson County is surrounded by 15 acres of vines and has stunning views of the mountains. The house has all the amenities you could wish for while keeping its charm. The farmhouse is a very private and idyllic residence. There is a front porch with a bench swing and a hammock, as well as a small flagstone patio with wrought iron furniture for your relaxation. The pool is around back and is fenced in. The large deck above the pool is excellent for basking in the sun or watching it set over the mountains. If you run out of wine, you can walk down to the winery's tasting room and stock up, listen to (occasional) live music, or enjoy a bottle on their patio for a change of pace. The beauty of Nelson County and the Cardinal Point Farmhouse will help make your stay one of the most relaxing you could ever imagine. **We do allow pets with an additional charge of $50/day. If you will be bringing your pet, please let us know and we will adjust the price accordingly (airbnb.com does not have an automatic fee to be added on when booking). All parts of the property are accessible EXCEPT THE BARN. This is a working vineyard, so there are tools, equipment and chemicals that are not appropriate for guest access. Someone should be available by phone or in person for any questions or problems you have. Our farmhouse is conveniently located on the same property as our winery(!): www.cardinalpointwinery.com. Also, within a few miles, there are three other wineries, three breweries, a distillery and a cidery. From May through October, nearby Nellysford hosts a phenomenal farmers' market. Charlottesville, with its vibrant arts and restaurant scene is 25 minutes away. On the other side of the Blue Ridge Mountains (just 15 minutes away), you can go to the movies, out to eat, grocery shop, etc in Waynesboro. But, honestly, there is a good chance you may not want to leave our farm at all. There is no public transportation in our area, but there are many services to take guests on winery and brewery tours. They are a great and worry-free way to sample what the area has to offer! As this is a working vineyard, occasionally there may be someone on the premises taking care of the grapes. We will be sure to let you know when someone will be on the property.

The Peony Cottage in Charlottesville

This private cottage is conveniently located between Crozet and Ivy. Perfect location for accessing Monticello Wine Trail, the Blue Ridge Parkway/Skyline Drive, Wintergreen Resort, and enjoying all University of Virginia events! 3 miles from Downtown Crozet & King Family Vineyard 4.5 miles from Chiles Orchard 8.5 miles from John Paul Jones Arena 10 miles from Blue Ridge Parkway - North Entrance 30 miles from Wintergreen Resort Join us as we watch the progress of our newly planted peony field!

Mountain Mama- Amazing Views! + Hot Tub!

MOUNTAIN MAMA - The home for gorgeous Blue Ridge Mountain views : ) Situated on a graceful 26 acres minutes off Rt. 151, our mountainside home is nestled within the beautiful Rockfish Valley and offers incredible views from every window in a truly unique and newly renovated home. Enjoy sunsets over 3600’ Humpback Mountain due west and sunrises lighting up the valley ridges. If you need time to be inspired by nature’s beauty, this home offers a rare breath of fresh air! Book your stay today!

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

Gorgeous Modern Mountain Home + Blue Ridge Views

GREENWOOD VISTA - Escape to our modern mountain home nestled along the Blue Ridge mountains. Whether you want to explore Shenandoah National Park, visit wineries, or relax in our hot tub with stunning mountain views, this gorgeous A-Frame home is the perfect place for you. We have thoughtfully appointed our home with everything you need to be comfortable. From a luxurious bedroom suite, fully equipped kitchen, to coffee and wet bar, sauna, outdoor grill, billiard table, and a cozy fire pit.

Crozet Cottage | Close to Wineries & DT Crozet

Enjoy a cozy getaway at our centrally-located carriage house, in the heart of sought-after Crozet, VA. Completely renovated in 2022, the carriage house feels brand new! Our space offers 1 queen bed and 1 full-bed pull-out couch. The space is .5 miles from downtown Crozet, 2.5 miles to King Family Vineyard and 3.5 miles to Chiles Orchard. It is equipped with a kitchen, a large closet (fits a pack n' play!), high speed internet and Apple TV. We have assigned parking spots in the driveway.

The Inn at Blue Mountain Brewery

The Inn at Blue Mountain is a 4,000 square foot Cape Cod-style home on 2 acres of wooded countryside adjacent to the larger grounds of Blue Mountain Brewery. The brewery is easily accessible via a private walkway. In addition to comfortable, well-appointed sleeping quarters, a fully-stocked kitchen, and game room with pool table, the Inn features a welcoming wrap-around porch, large outdoor deck and patio areas, fire pit, hot tub, tiki bar, and gorgeous views of the Blue Ridge Mountains.

Ivy Rose Cottage nestled b/t Cville & Vineyards

The Ivy Rose Cottage bestows an exceptional ambiance that will captivate your heart. Whisk yourself away to this two bedroom cottage located in Ivy halfway between the Shenandoah Park/Brewery Trail and Charlottesville, home of UVA. The Ivy Rose Cottage, designed and handbuilt by the hosts, is an enchanting mix of cypress, timber frame, copper trellis work, pergolas and other architectural treasures. Fully equipped kitchen and a washer/dryer for those lengthier stay conveniences.

Farmhouse on 151 w/ Firepit, Huge Yard, Mtn Views

Our two story, 1904 farmhouse is just off Route 151 and close to wineries, breweries, hiking trails, and the Blue Ridge Parkway. It's only 25 minutes from Wintergreen Resort, and 30 minutes from Charlottesville. We have fast Wi-Fi, a desk, 2 acres to run and play, and plenty of indoor space to relax. Enjoy the view around the large stone fire pit. Bedrooms have recently been updated! We have a gas fireplace with a remote control that is available for use in the cooler months.

The Barn at Haden near Wineries and C'ville

The Barn at Haden is a custom well appointed finished 2 bedroom, 1 full bath space elevated above a detached 3 car garage with a large outdoor private deck. It features a fully equipped gourmet kitchen with high end finishes. Whether staying for a night or for the weekend, it is an experience to enjoy the easy living Crozet has to offer. Walkable/bikeable to downtown Crozet, 2 miles to King Family Vineyard & Chiles Peach Orchard and 15 minutes from Charlottesville.

Guesthouse at Hamilton Oaks

Escape to our guesthouse on a little farmette. This peaceful setting tucked away on several acres along a creek with nature trails is the perfect mountain getaway. We are conveniently situated near quaint wineries, breweries along with hiking and the Blue Ridge Parkway that is a short hop, jump and a skip away. Every effort has been made to keep this a green haven, chemical and synthetic scent free, so you can leave recharged and rested. Non-smoking