Family-friendly holiday rentals in Wintergreen Resort

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Spacious sleeping loft. Perfect romantic escape, friends getaway, or personal retreat. Workout area/sitting room. Fresh eggs (in season), wine, tea, coffee. 1G Internet, SMART TV. A/C. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from App. Trail, Wintergreen Resort, breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, & antique shopping.

The Cottage at Spindle Hill: an Artist’s Farm

Relax and unwind in this fabulous handcrafted cottage— every detail has been considered! Beautiful mountain setting on small, historical farm just off Blue Ridge Parkway, the heart of Virginia wine country. Deep, hand-built cedar hot-tub. Minutes to the Appalachian Trail and Wintergreen resort. An easy walk to public trails, Devil's Backbone Brewery and Bold Rock Cidery. Beautiful gardens, hammocks, featured in design blogs. High-speed fiber internet. Library. Hens. Miniature Goats. EV Charger.

Wintergreen Bunkroom Private Suite BEST Location

Wintergreen Resort, (4.6 mi) Bold Rock Cider (1/2 mile/walking distance) Devil’s Backbone, Blue Toad Cider. Hazy Vineyard. Blue Mountain Brewery. Veritas Vineyard. Afton Mountain Vineyard. Rockfish Glider Port (backyard) Off 151, in Nellysford. Attached suite, PRIVATE entrance & bath, self check in. NOT a shared space with owner. 2 rooms sleep 6 MAX. Bunkroom sleeps 4, living room sleeps 2 on sofa bed. Clean and sanitized to standards. Microwave, mini fridge, wet bar. NOT a full house rental.

The Bear Dance Cabin at Wintergreen Resort

Tucked back in the woods in the Wintergreen Resort, we're on the top of Wintergreen Mountain, elevation just under 4k, near all the resort's amenities. Our family built on Wintergreen Mountain after learning how unique and beautiful the seasons are here. The cabin quickly became a new member of the family and we can’t imagine not having her in our lives now. Ten years after building we decided to provide short term rental and the experience has been beyond what we had ever imagined. Enjoy!

Blue Ridge Cottage - 3 Miles to Wintergreen

Our little piece of Blue Ridge Heaven is ready to share! Cozy - 2 bedrooms (one king, one queen), 1 bath, 956 square feet - well appointed in a terrific location! Beautiful mountain view from the 360 square foot, partially covered deck; fiber optic TV and wi-fi; South Fork of the Rockfish River out back. 3 miles from Wintergreen Resort, 1 mile from Devil's Backbone; Close to great hiking/biking, and many wineries, breweries, cideries, and distilleries (if you're into that kind of thing!)!

Eight Minute Walk to Everything

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

3 BR 3 BA, 2 story condo in Highlands

Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Dogwood Suite at Open Heart Inn

Welcome to your country retreat! This unique section of the farmhouse was originally built in 1840, and features a cozy, king-sized bed. Relax on your private front porch, enjoy the views from the back patio, explore our 10 acres of farmland, take in the dogwoods and beautiful flowers, and get away from it all! Minutes from the Appalachian Trail, Devil's Backbone, and much more-- we are perfectly located to explore the trails, breweries, and wineries of scenic Nelson County.