Family-friendly vacation rentals in Waynesboro

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Waynesboro

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

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Guest favorite

Cabin in Roseland

4.96 out of 5 average rating, 676 reviews

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.

Guest favorite

Tipi in Fairfield

4.98 out of 5 average rating, 1,110 reviews

Tipi with a great view of the Blue Ridge Mountains

Our small family farm is conveniently located 10 minutes from Interstates 81/64 and historic Lexington, Virginia. The Tipi has amazing views of the Blue Ridge Mountains and all the wonders our little farm and community has to offers. We are convenient to many local attractions like hiking, swimming, brewery and vineyard tours and yet secluded enough to heal your stress, enjoy time with your family or simply a special time away from the grind. Come stay with us! You deserve sincere hospitality!

Guest favorite

Cabin in Nellysford

4.96 out of 5 average rating, 195 reviews

Tiny Luxury Retreat: Lake, Hikes, Brews & Vines

Welcome to our luxurious tiny house nestled in the heart of Nelson County, Virginia. This enchanting retreat, surrounded by the majestic Blue Ridge Mountains, offers an unparalleled experience in a landscape dotted with wineries, breweries, distilleries, and sprawling farmland. This luxury tiny house was built in 2022 and is available for couples, solo travelers, or a small family wanting to explore this beautiful stretch of the Blue Ridge Mountains. FREE Electric Vehicle Charger on-site.

Guest favorite

Cottage in Roseland

4.99 out of 5 average rating, 198 reviews

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!)!

Superhost

Rental unit in Afton

4.87 out of 5 average rating, 300 reviews

Best Spot on the Wine/Brew Trail!

Charming, private, efficiency apartment located in the center of winery/brewery country! This efficiency offers fiber internet (super fast)! Less than a minute to Blue Mountain Brewery, Flying Fox Vineyard, and Valley Road Vineyard. Less than 5 minutes to Veritas Vineyard, Cardinal Point Vineyard, Silver Back Distillery, Afton Mountain Vineyards. 5-10 minutes to Bold Rock Cidery, Devils Backbone Brewery, Brewing Tree Brewery, Mountain Meadery, Hill Top Berry Farm, and so many more.

Guest favorite

Rental unit in Rockfish

4.99 out of 5 average rating, 170 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.

Guest favorite

Guest suite in Charlottesville

4.94 out of 5 average rating, 500 reviews

Relax and Breathe In Nature at the Forest Haven!

Retreat from the stress and noise of the world for a while. Come to the Forest Haven where you can enjoy peace and quiet, yet still be just a short drive away from the restaurants and attractions in Charlottesville. Shenandoah National Park and the Blue Ridge Parkway are within an easy drive. This immaculately clean and modern apartment is located in a beautiful wooded setting surrounded by nature and wildlife. Once you get here, you may not want to leave!

Guest favorite

Guesthouse in Crozet

4.86 out of 5 average rating, 296 reviews

Stylish Carriage House Suite near Crozet center

Peaceful retreat walkable to downtown Crozet (coffee shops, galleries, restaurants, yoga.) One bedrm, large bathrm with clawfoot tub, stovetop kitchen with granite countertops, electric fireplace, reclaimed barn wood features, and private deck. (Access to main house yard w permission, each time.) One small non-shed dog on Nexgard with permission and fee. (Some other breeds with discussion and sweep on check-out.) Find us for winery tours at CrozetTrolley.

Guest favorite

Cabin in Faber

4.98 out of 5 average rating, 156 reviews

Buck Creek Cabin In The Woods~Adorable and Private

~Buck Creek Cabin is private, cozy & clean ~Located within a wooded area on 33 rural acres ~Walking paths through woods and meadow ~Ample deck and porch for dining, relaxing, and viewing the moon ~Secluded and quiet setting, perfect for wildlife sightings ~Very near breweries, wineries, and distilleries ~Half an hour from Charlottesville, the AT, Blue Ridge Parkway, & Wintergreen Resort. ~High-speed fiber optic internet ~Delicious spring-fed drinking water

Guest favorite

Cottage in Crozet

4.88 out of 5 average rating, 234 reviews

A-Frame Pawpaw 2 BR Cabin, Lake, Hike & Canoe

Eco-friendly cottage overlooks lake in mountains 1 BD w/ queen, ladder to sleeping loft w/ two twins, double futon in living-room. Bath with tub. Deck with charcoal grill. Only a few yards from water’s edge. Onsite walking trails with mountain bikes, canoes, and fishing. Family friendly! Pets welcome with additional $45 fee. Wi-Fi in this cottage sometimes needs owner to reset. Near the Shenandoah National Park!

Guest favorite

Tiny home in Linville

4.99 out of 5 average rating, 667 reviews

The spring house at Thistle Hollow

Beautifully renovated spring house on the grounds of the 1800s Peter Breneman House. Soak up peace and quiet in one of the most beautiful corners of the Shenandoah Valley. Enjoy starry skies, sunrises, and birdwatching from your private porch. 9 minutes from Eastern Mennonite University, 13 minutes from James Madison University, and 45 minutes from the entrance to Shenandoah National Park.

Guest favorite

Cottage in Afton

4.99 out of 5 average rating, 161 reviews

Beautiful, Remodeled Eco Cottage in Afton

Hike our 2 miles of our beautiful, well maintained trails. The cottage and property are very serene and quiet. Ideal location: Only 1.5 miles to Route 151. About 3.5 miles hiking provides access to the Appalachian Trail from the cottage. Explore local wineries, breweries, and cideries.