Vacation rentals in Greenwood

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

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!

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

Idyllic Cottage Retreat

⭐️ Condé Nast Traveler Approved ⭐️ Cozy cottage nestled on a historic 400-acre Blue Ridge Mountain farm abutting Shenandoah National Park. Every space inside this cozy cottage is creatively styled, with tons of perfectly imperfect charm. Outside, a hammock beneath the elm trees, fire pit and grill, all allow for enjoying the splendor of this peaceful enclave. Excellent day-tripping to many of central Virginia's celebrated wineries and breweries, as well as scenic drives and hiking trails.

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.

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Welcome to Towler Cottage, a getaway in the heart of Route 151 in Afton. The cottage is within minutes from the best wineries and breweries, great local trails, and the Blue Ridge Parkway! Relax in the hot tub on the rear deck, or sit out by the fire pit and gaze at the stars. Enjoy great mountain views from the front porch rocking chairs. With one bedroom with a queen bed, plus a pull-out couch in the living room, the cottage is perfect for couples. Located 25 minutes from Charlottesville.

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

Mountain View Getaway Yurt

Come enjoy country living in beautiful western Albemarle county. Our yurt is on a 13 acre property on a quiet country road. (My husband and I also have our home about 200 ft away from yurt). The yurt features a relaxing outdoor claw foot tub/shower with beautiful country views. The private bathroom is situated on the deck of the yurt. The pool is a shared space directly behind our home. The wooded part of the property is private with a beautiful walking trail for you to enjoy.