Family-friendly holiday rentals in Nellysford

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.

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

The #4 Loblolly Cottage is an eco-friendly cabin overlooking a lake. Small 450 sq ft, cottage has a queen size bed in the primary bedroom, bunk beds in the second bedroom and a full size futon in living room. Kitchenette equipped with modern appliances and breakfast table. Bathroom and shower. Wi-Fi. Private porch. Pets are welcome for an additional fee. Hike, canoe, fish and bike onsite on a 129 acres. Close by wineries, 15 min to Shenandoah National Park. This cabin is ideal for families!

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!

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

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from the dog park, and picnic area it’s an ideal location.

Bright, Spacious Home Perfect for Groups (5 Beds)

Perfectly situated 1 mile from Downtown, 2 miles from UVA and a short drive to the interstate for vineyard access, this home is the perfect fit for large families, weddings, bachelorette parties! With 2,000+sq ft, 5 queen beds, and a fenced-in backyard, there is plenty of room for all! Early check-in is usually available upon request, depending on other bookings the week of your stay. Please see our guidelines below for hosting bachelorette parties in the home :)

Crozet casa w/ firepit & hot tub in wine country

Welcome to our home in Crozet, just 15 minutes west of Charlottesville, off Hwy 64 and Route 250. We're close to restaurants, wineries, breweries, shops, and outdoor spots like Skyline Drive and hiking trails. Enjoy our hot tub, fire pit, large deck, BBQ, and well-stocked kitchen. All linens are provided. This is our personal home, and we love sharing it with guests. A $60 cleaning fee applies for one dog. We hope you have a relaxing stay. Thank you!

Belmont Classic/Modern Reno, Walkable

Custom renovated, family home in the historic Belmont neighborhood of Charlottesville. Well appointed space, embracing a blend of mid century style. Walkable to some of CVille's best restaurants and breweries. Easy 5 min walk to the Downtown Mall, Sprint Pavilion, and Arts Park. Great neighbors, in a tree-lined, family friendly part of town. Easy access to the burgeoning Cville wine scene, Grounds for alumni events and walks down memory lane.

Greenleaf Grove

Charming 1947 Cape Cod Style home with three bedrooms and two updated bathrooms. The upstairs is big attic space with double bed and private bathroom. Modern kitchen with all new amenities. The home is 1.7 miles from UVA Rotunda and walking distance to parks, restaurants and downtown mall. Open to inquiries about any dates that do not appear open on calendar and price reduction for visits greater than 7 days