Holiday rentals with a kayak in Wintergreen Resort

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!

The Stilt House at Perkins Hollow

Welcome to The Stilt House at Perkins Hollow Retreat, a one-of-a-kind elevated cabin tucked among the trees in the heart of Virginia Wine Country. Perched above the forest floor, this cozy retreat offers a treehouse-like experience surrounded by over 60 acres of private woods and mountain scenery. Perfect for couples, solo travelers, and outdoor enthusiasts. Spend your days exploring nearby wineries, breweries, and hiking trails, then return to your private retreat to relax beneath the stars.

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.

Treetop Sunset Deck, 2 Upscale King Bedrooms

Enjoy a top-floor mountain sanctuary at The Haven at Wintergreen! Overlooking scenic treetops and the 18th green, this private end unit features 2 king bedrooms with plush linens, a cozy stone fireplace, full kitchen, and a deck with stunning sunset views. Walk to hiking trails, Founders Overlook, and The Spa at Wintergreen, or hop on the seasonal ski shuttle. Minutes from the Blue Ridge Parkway, local wineries, and craft breweries. Reconnect with nature and find your mountain reset here!

Crabtree Falls Mountain Hollow Guesthouse

Get back to nature in a river front apartment nestled in the Blue Ridge Mountains. Adjacent to the owner's home, above a rarely used garage, the 70-acre well-maintained property offers mountain forests and a pond view with outdoor experiences for star gazing, and campfires. Escape electronic devices to explore area attractions, waterfalls, hiking trails, scenic drives, and fishing. This new rental is craftsman built with wood interior. We also love hosting our other cabin, Parr's Camp.

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!

Large historic home on 7+ acres.

Heritage Hill Bed and Breakfast is a charming historic home centrally located in Waynesboro, Virginia. Located just 6 miles from where Skyline Drive connects with the Blue Ridge Parkway and the Appalachian Trail, the 4,300 sq. ft colonial style house is situated perfectly on 8 acres. This home offers large bedrooms & modern bathrooms, a gourmet kitchen, elegant dining & living areas, and picturesque views of the Blue Ridge Mountains. For event information visit - heritagehillbnb

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.

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.

Riverfront Room 2

This is a roommate situation. I have an available bedroom in my five bedroom, two bathroom house located on the South River in Waynesboro. Common spaces are shared. I'm looking for someone that would at least stay for a month or more but would consider less time for the right person. We all work full-time. No couples, no kids, no smoking, no drugs, no vaping, etc. Great location, easy drive to plenty of local breweries and restaurants.

Parr's Camp - Nothin' Fancy Fish Camp

Experience the Blue Ridge Mountains in a 1940’s fishing cabin! Guests adore Parr's Camp-it's rustic outside & restored charm inside. A private pond & the Tye River flow steps away for you to enjoy the ever-changing mountain stream. Our family friendly cabin allows children areas to explore nature & enjoy marshmallows over the campfire. We have enhanced our cleaning procedures & taken care to properly disinfect between reservations.