Family-friendly vacation rentals in Timberlake

Guest suite in Nellysford

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.

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.

4.97 out of 5 average rating, 936 reviews

A spacious studio apartment features warm wooden paneling and flooring. A vibrant area rug lies beneath a large bed with white linens, while a red armchair adds a pop of colour. The kitchenette, visible in the background, includes a dining table and chairs, with windows allowing natural light.

Loft in Buchanan

Edifice Rex

Edifice Rex, a 300 square foot studio apartment, is only one mile and less than 2 minutes from Interstate 81 yet offers a very bucolic, peaceful setting. Countless cultural, historical and recreational opportunities exist within a 30 mile radius. The James River and Appalachian Trail are but minutes away. The name, "Edifice Rex" is to honor the caretaker on the property, a German Shepard named Rex. You will not have to interact with him ( he wears a radio collar) but he welcomes attention.

Cabin in Wintergreen Resort

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.

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!

4.86 out of 5 average rating, 198 reviews

A welcoming porch features several wooden rocking chairs positioned on a wooden floor, inviting relaxation. Planters with greenery enhance the outdoor space. In the background, a flag is displayed, and the surrounding lawn is lush, providing a serene setting.

Cottage in Buena Vista

The Farmhouse at Balcony Downs

This cozy farmhouse, built in the 1930s, is a hidden gem nestled at the foothills of the Blue Ridge on the historic Balcony Downs estate. With an abundance of outdoor activities on site and nearby, Balcony Downs is a wonderland for the adventurous. Due to the age of this cottage, it has some quirks that you should consider before booking: 1. The bathroom is on the 2nd floor. 2. The stairs are open and steep. 3. The shower is small and may be difficult for tall or larger individuals.

Condo in Wintergreen Resort

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.

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.

4.89 out of 5 average rating, 654 reviews

The image showcases a collage of four areas of the house. A modern kitchen features stainless steel appliances. The welcoming front porch includes a seating area. A calming bedroom with light green walls contains a spacious bed. A cozy living room is furnished with a comfortable sofa and coffee table.

Apartment in Roanoke

BRAND NEW DOWNTOWN HOUSE SLEEPS 5 HIGH END LUXURY

Great brand new private place less then a mile away from downtown! Everything has been fully renovated, with a fully stocked house, every possible thing you could imagine is in this house for your use! No need to bring anything but yourself and clothes. 2 huge bedrooms with queen size Tempur-Pedic memory foam like beds along with a movable foldaway twin size bed. Can sleep 5 very comfortably. Plenty of parking available. Every room has a TV and there is WiFi throughout the house.

Condo in Wintergreen Resort

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.

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

4.84 out of 5 average rating, 314 reviews

Cabin in Coleman Falls

Green Needles Christmas Tree Farm Cabin/Lynchburg

Our cabin is 600 sq ft with a large covered porch. We have 1 queen size bed, a double & single bunk combination, and full kitchen. We have 2 sources of heat, propane and electric both which make some noise when they run. 42 acres of Christmas trees, wooded trails, a stream that runs throughout the property, foot bridge and fields. A short 10 min hike will take you to our Ridge with a gazebo. We are 25 min from LU, 15 min from the Lynchburg area and 15 min from the Blue Ridge Pkwy.

4.98 out of 5 average rating, 187 reviews

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

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.

4.79 out of 5 average rating, 674 reviews

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

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!

4.78 out of 5 average rating, 110 reviews

A wooden fence encloses a backyard, highlighted by a swing seat positioned beneath a shaded canopy. Tall evergreen trees provide privacy and a natural backdrop, while a clear blue sky can be seen above, creating a serene outdoor space.

Home in Hot Springs

Charming Getaway Cottage

THE SKI SLOOPS AT THE HOMESTEAD ARE OPEN !!! Time for a vacation in the mountains at my cozy cottage less than 2 miles from the Homestead Resort. This charming cottage is 1100 sq. ft. and less than 1 mile from the Homestead Resort. Close proximity to Warm Springs, and all the attractions Bath County, Va. offers. Perfect for hiking, golf, skiing, hunting, fishing, floating in the Warm Springs Pools and a family getaways. Pet friendly.