Family-friendly vacation rentals in Wintergreen Resort

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Top-rated family-friendly rentals in Wintergreen Resort

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

A wooden ladder leads to a cozy sleeping loft, enhancing the cottage's open design. A bookshelf filled with various books is seen beside a small seating area with a plush, patterned chair. Warm wood tones dominate the floor and ceiling, creating a welcoming environment.

Farm stay in Nellysford

4.91 out of 5 average rating, 570 reviews

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.

Top guest favorite

A grassy area is framed by tall trees, providing shade and a sense of privacy. A rustic wooden bench sits invitingly in the foreground, while a swing is visible in the background, creating a serene outdoor space for relaxation.

Guest suite in Nellysford

4.98 out of 5 average rating, 195 reviews

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.

Superhost

A rustic cabin constructed of timber sits amidst a wooded area, showcasing a wraparound porch with steps leading up. Large windows provide glimpses of the surrounding trees, while gravel paths lead to the entrance, enhancing the natural setting.

Cabin in Crozet

4.86 out of 5 average rating, 101 reviews

#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!

Guest favorite

A sweeping aerial view captures the snowy landscape of Wintergreen Resort at sunset, with vibrant colors illuminating the sky. Slopes are visible, lined with trees and softly lit by lights. The resort buildings are nestled below the mountains, framed by winter scenery.

Cabin in Wintergreen Resort

4.87 out of 5 average rating, 127 reviews

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!

Guest favorite

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

Condo in Wintergreen Resort

4.94 out of 5 average rating, 226 reviews

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.

Top guest favorite

A scenic view of rolling hills is captured at sunset, with soft hues of orange, pink, and purple coloring the sky. In the foreground, a glass of clear liquid rests on a wooden railing, enhancing the tranquil atmosphere.

Condo in Wintergreen Resort

4.99 out of 5 average rating, 158 reviews

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

Top guest favorite

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Apartment in Rockfish

4.98 out of 5 average rating, 187 reviews

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.

Superhost

The bathroom features a clean and functional design, highlighted by a white vanity with a sink and ample counter space. A mirror and basket for storage are mounted above the sink. Natural light enters through a window, enhancing the fresh atmosphere.

Cottage in Afton

4.79 out of 5 average rating, 674 reviews

Cottage on Wine/Brew Trail!

Cottage right in the center of all the wineries, breweries, distilleries, cideries, Shenandoah National Park, hiking, App.Trail, Blue Ridge Pkwy, Wintergreen Resort.Pets welcome for an added fee ($40). Located on 151 -"alcohol alley". Literally seconds to Blue Mountain Brewery or Flying Fox Vineyard & a minute or two drive to Veritas, Cardinal Point, Afton Mt, Silverback, Valley Rd and more! Fiber internet, disinfected--couldn't ask for a better spot!

Top guest favorite

A bright dining area features a colorful tablecloth over a large dining table surrounded by black-and-white patterned chairs. Natural light floods in through large windows, highlighting art on the walls. An outdoor grill is visible through the glass doors, enhancing the inviting space.

Home in Crozet

4.97 out of 5 average rating, 197 reviews

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!

Guest favorite

The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.

Condo in Wintergreen Resort

4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

Come enjoy beautiful year round views in this lovely two bedroom/ two bath Condo. It has a wood burning fireplace for cold winter nights. On weekends during ski season you can catch the shuttle to the slopes. There is a KING size bed in the Master bedroom and 2 twins in the other. Enjoy two full bathrooms. You can cook in the fully equipped kitchen. In the summer you can enjoy one of the many hiking trails .

Top guest favorite

A cabin exterior is showcased, featuring a deck with various chairs and a table for outdoor dining. Large windows reflect natural light, complementing the surrounding greenery. A stone feature is visible below the deck, adding organic texture to the scene.

Cabin in Wintergreen Resort

4.99 out of 5 average rating, 133 reviews

Family Friendly Home with All Necessities Included

Cute 3 bedroom cabin on the golf course with a view of the valley. Easy access to the black diamond ski slopes and Wintergarden Pool and Spa down the street. Walking trail to the lodge is located at the end of the street. Coming with small children? We have a pack n play, highchair, and gate for the stairs as well as games available.

Top guest favorite

A serene river flows gently through a wooded area, with sparkling waters reflecting sunlight. Leafless trees line the riverbank, and a backdrop of a forested hillside adds depth to the tranquil scene.

Cabin in Faber

4.97 out of 5 average rating, 130 reviews

Cabin 140 Acre,Private, Peace, Mile River trails!

AWESOME FOR HIKING AND BIKING ON THE LAND, GREAT TRAILS AND AMAZING VIEWS! Fresh linens, blankets and towels are provided for you. Kayak are available for you (It is a gorgeous 2 hours trip down the beautiful Rockfish river) You'll need 2 vehicles for the kayak trip. $100 You can hike or drive to the river from the cabin.