Family-friendly holiday 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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Top guest favourite

Cabin in Roseland

4.96 out of 5 average rating, 703 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 favourite

Farm stay in Nellysford

4.92 out of 5 average rating, 586 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 favourite

Home in Faber

4.99 out of 5 average rating, 149 reviews

33‑Acre 2 BR Lodge Hidden in the Blue Ridge

Nestled on 33 private acres, Buck Creek Lodge strikes the perfect balance between country serenity and convenience. Artist‑designed trails meander from Buck Creek to a hidden pond and through lush, forested slopes. You’re just minutes from local breweries, wineries, and distilleries, and a short drive to the Blue Ridge Parkway, AT trailheads, Wintergreen Resort, or 30 min to Charlottesville. A spacious covered porch—with pond and mountain views—beckons for morning coffee and evening unwind.

Superhost

Flat in Afton

4.87 out of 5 average rating, 347 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.

Top guest favourite

Farm stay in Raphine

4.98 out of 5 average rating, 380 reviews

The Cottage at Hidden Valley Farm & Barn

Welcome to Hidden Valley! When booking your stay, you'll have exclusive access to our three bedroom/two bathroom guest cottage! You'll be surrounded by mountainous views and pastures. Snuggle on the wrap around porch, roast marshmallows in the fire pit, and visit with horses, cattle, and our Sulcata tortoise! This is a working farm and you'll frequently see and hear farm machinery(tractors/atvs/etc.), livestock (cattle/horses/a donkey/4 dogs/a cat),and wildlife (coyotes/turkeys/deer).

Guest favourite

Tiny home in Charlottesville

4.94 out of 5 average rating, 718 reviews

Oxford Cottage: Cville’s favorite tiny home!

This 350 sq ft cottage is a tiny home concept space, boasting an airy entry, living area, storage landing, kitchenette, bathroom and sleeping loft. Perfect for a romantic getaway, a work retreat, a stop through town on the way to another location, a small family, or a group of friends participating in the many events held in Charlottesville- weddings, concerts, triathlons. Accommodates 1-4 people looking for a relaxed, stylish, modern and comfortable place to stay.

Top guest favourite

Flat in Rockfish

4.98 out of 5 average rating, 195 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 favourite

Apartment in Staunton

4.83 out of 5 average rating, 395 reviews

Third & Thornrose, Staunton Condominium

Our guests stay upstairs in our 1929 American Foursquare house. Central air; separate entrance, wooden floors. Daily, weekly or monthly rates. Small, fully-equipped kitchen with stove and refrigerator, small dining room. The bathroom has a tub and shower. Television with Netflix. Wifi and off-street parking. Two bedrooms (queen-sized bed, two XL twin beds), living room. Short walk to Gypsy Hill Park, 1 mile to historic downtown (Trolley). Small town, Big Magic!

Top guest favourite

Guest suite in Charlottesville

4.94 out of 5 average rating, 527 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!

Top guest favourite

Flat in Weyers Cave

4.93 out of 5 average rating, 269 reviews

Plane View Retreat

You’ll love my place because of the quiet, scenic location. Plane View's in the heart of the beautiful Shenandoah Valley. We're across the runway from Shenandoah Regional Airport and within 30 minutes of Skyline Drive. There's hiking, white water rafting & Civil War sites nearby. We're 2 hours from Washington DC and Richmond. We have 360 degree mountain views. My place is good for couples, solo adventurers, and families (w/kids). No wifi, no pets.

Top guest favourite

Tiny home in Linville

4.99 out of 5 average rating, 718 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 favourite

Loft in Bridgewater

4.92 out of 5 average rating, 558 reviews

Private Studio Apt Retreat

This light filled, airy studio apartment is the perfect space to meet all your needs. Located on a private second floor of a detached garage in one of the most unique homes in the area. Full kitchen, dining and living room. Spacious and open, 600 sq feet of relaxing space. Located in heart of the Shenandoah Valley.