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The Haven at Wintergreen 2 king, 2 bath, golf view

Wake up to the fresh mountain air and spend the day hiking, golfing, skiing, or exploring the Brew Trail. Then return to your comfortable mountain home overlooking the 18th green. The Haven at Wintergreen is a beautiful top-floor end-unit overlooking Devils Knob golf course with seasonal Blue Ridge Mountain views. Walk to The Spa at Wintergreen and hiking trails, with year-round resort activities and a peaceful mountain setting designed for comfort. Two King bedrooms, two bathrooms, sleeps 4.

Peaceful, Luxury 2 Bdrm, Blue Ridge Mtn Views

COME ENJOY: *Mountain Vistas with Gorgeous Sunrises/Sunsets Year Round. *1/2 mile to Shenandoah Natl. Pk, Appalachian Trail, Skyline Dr, Blue Ridge Pkwy *Magical 25 mile Long Range Blue Ridge Mountain View *3 minutes to Exit 99 at I-64 *5 Minutes to Waynesboro w/5 grocery stores and all the amenities of a small town *Easy drive to Augusta Health, UVA Hosp., Waynesboro, C-Ville & Staunton *Pet Friendly *Dining Table w/Chairs Can be Used as Work Station *Washer/Dryer We hope to see you soon!

Very Private Cabin on 100 Acres - Howl at the Moon

"Into the forest I go... to lose my mind and find my soul." -John Muir Incredible cabin nestled in the center of 70 very private acres. Relax and unwind to the sights and sounds of frogs, crickets, & owls. Ideal for families and couples. The Cabin offers close proximity to the James River & tubing, UVA, and many wineries. You will see millions of stars and gain the serenity that can only come from nature. The Cabin is also only 20 minutes away from all that Charlottesville has to offer!

James River Cottage with 2 Kayaks to use.

Escape to a tranquil one-bedroom cottage getaway located along the serene James River. This charming retreat offers direct access to the river, allowing you to relax and unwind in a picturesque setting. Enjoy the convenience of a picnic table where you can savor meals or simply take in the soothing sounds of nature. Inside the cottage, you'll find a well-equipped kitchen that invites you to prepare delicious meals at your own pace. The bathroom features a refreshing shower. Kayaks available

Spindle Hill Farm’s Schoolhouse | Fire pit, Pond

A solar-powered 1932 schoolhouse on 50 acres of farm & forest— huge original windows, hardwood floors, two ponds with a dock, and a kitchen stocked like it means it. Three bedrooms, two colorful bathrooms, sleeps six. Fireplace. Private hiking trails through the woods, a gas fire pit, and charcoal grill. Fast fiber internet. EV charger. Hidden and private, but 2 minutes from Devils Backbone and right in the heart of the 151 Brew Ridge Trail. An honest-to-goodness one of a kind. Come see it.

SkySpace Sanctuary

This beautiful secluded hilltop home offers breathtaking panoramic views of the Blue Ridge Mountains and the graceful James River under an endless sky. Enjoy quiet, peaceful times alone and quality time with loved ones and friends. Relax in a family hot tub. Prepare meals in the spacious kitchen or grill on the terrace. Children are welcome. Wheelchair accessible rooms are available for people with disabilities. Perfect for longer stays, family reunions, retreats, and small weddings.

Cozy Mountain Cottage

Welcome to your next mountain cottage getaway. This beauty is located in the heart of Afton, Virginia along route 151 known as "Alcohol Alley". Located 2 miles from Blue Mountain Brewery, 3 miles from Flying Fox Vineyard. A 5-minute drive will bring you to a host of wineries, breweries, and distilleries including Veritas Vineyards, Hazy Mountain Vineyards, and Valley Road Vineyards. We love animals so pets are welcome with a $50 additional fee, per pet. Restaurants can deliver!

Luxury Cottage | Outdoor Tub + Mountain Views

Soak in a private outdoor bathtub beneath the stars, wake to mountain views from your king bed, and open an entire wall of glass to bring the Blue Ridge Mountains inside. Welcome to The Cottage at Perkins Hollow Retreat! Located in Nelson County, just minutes from the Nelson 151 Brew Trail, award-winning wineries, breweries, hiking, and only 25 minutes from Charlottesville, The Cottage is the perfect destination for a romantic getaway, anniversary, honeymoon, or peaceful retreat.

Coolcation, Pool + Amazing Views

⭐⭐⭐⭐⭐ Guest Favorite “One look at the view and you’ll be instantly transported to your happy place. Even my 5-year-old was impressed.” Welcome to Mountain Dreams—your cozy 2 BR, two-level getaway at one of Wintergreen’s highest points. With stunning views and a cozy atmosphere, you'll soak up panoramic mountain views at The Ledges. Escape to our serene retreat, nestled in nature, offering a peaceful environment for relaxation. Just a 3-minute drive to the Mountain Inn.

The Brew Ridge Trail's Most Unique Home. Sleeps 12

"Guest Favorite" Top 5% of Homes on AirBnB. Rated 4.96★ by 100's of guests. Dogs welcome! 42x SuperHost property. Your Brew Ridge Trail Adventure starts here. Afton’s top-rated Airbnb, this bright, spacious 3,300 sq ft home was extensively renovated in 2026 with brand-new amenities. Minutes from Wintergreen, the Brew Ridge Trail, breweries, wineries, hiking, golf, and the Blue Ridge Parkway. Perfect for friend getaways, reunions, and unforgettable weekends.

Historic 1870s Log Cabin near Charlottesville

Large Historic, Restored 1870's Log Cabin sleeps up to 15 people. Secluded mountain location, 4 bedrooms, 1 loft, 4 bathrooms. Escape the heat of the city and suburbia for fresh mountain air, mature forest canopy, historic ambiance, stone fire pit surrounded by Adirondack chairs. Coffee klatch with friends and family on the wide open porch, forest bath afternoons, grill and bar-b-que evenings around the fire. Enjoy a special long weekend with family and friends.

Woodson's Mill House

Conveniently located near Charlottesville, Wintergreen, and the Blue Ridge Pkwy, this idyllic Craftsman style home offers the perfect opportunity for couples weekends filled with excursions to local wineries, breweries, and restaurants, or quiet family getaways spent exploring the property's woods, lake, and historic Woodson’s Mill. This property offers the best of both worlds and is centrally located to all that the heart of the Blue Ridge Mountains has to offer.