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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Guest favourite

Tent in Fairfield

4.98 out of 5 average rating, 1062 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!

14–21 Mar

$209 NZD per night

Guest favourite

Guest suite in McGaheysville

4.98 out of 5 average rating, 421 reviews

Cozy 'For-Rest Retreat' by Nat'l Park, Resort, JMU

Solo travelers, couples, or two adults will love our homey (NOT chic, sleek, or spare) lower-level private suite set in the 4-season Massanutten Resort in lovely Shenandoah Valley. We are 3-8 mins to fun seasonal activities (WaterPark, trail rides, slopes, golf, go-karts, etc.); 15 mins to Shenandoah Nat'l Park's Swift Run Gap entry; 18-20 mins to JMU; 5-60+ mins to restaurants, wineries, antiquing, breweries, caves, hiking, biking, history sites, river sports, Amish markets, country drives+!

29 Nov – 6 Dec

$145 NZD per night

Guest favourite

Cabin in Nellysford

4.98 out of 5 average rating, 162 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.

21–28 Feb

$340 NZD per night

Guest favourite

Cottage in Roseland

5.0 out of 5 average rating, 178 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!)!

27 Aug – 3 Sep

$271 NZD per night

Guest favourite

Condo in Wintergreen Resort

4.95 out of 5 average rating, 199 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.

7–14 Oct

$215 NZD per night

Guest favourite

Apartment in Afton

4.87 out of 5 average rating, 260 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.

14–21 Aug

$257 NZD per night

Guest favourite

Cabin in Faber

4.98 out of 5 average rating, 139 reviews

Buck Creek Cabin In The Woods~Adorable and Private

~Buck Creek Cabin is very private, cozy and clean ~Delicious spring-fed drinking water ~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 ~Access to stone-accented designer gardens ~Secluded and quiet setting, perfect for wildlife sightings ~Very near breweries, wineries, and distilleries ~Half hour from Charlottesville, the AT, Blue Ridge Parkway, Wintergreen resort.

19–26 Jul

$311 NZD per night

Guest favourite

Guest suite in North Garden

4.97 out of 5 average rating, 287 reviews

Private & Spacious Apt Near Cville in Wine Country

Private apartment (for up to 4) in gorgeous southern Albemarle County - 1 mile from Pippin Hill & great launching spot for countless other wineries, breweries, cideries, hiking and everything else Cville has to offer! 750 sq ft with separate keyed entry for complete privacy includes large bedroom with king bed; living room with 60" TV, futon (sleeps 2), eating area, mini-fridge, Keurig & microwave; and large bathroom with two sinks. 15 minutes from downtown Cville.

20–27 Oct

$203 NZD per night

Guest favourite

Apartment in Weyers Cave

4.93 out of 5 average rating, 242 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.

4–11 Sep

$189 NZD per night

Guest favourite

Cottage in Crozet

4.88 out of 5 average rating, 215 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!

4–11 Feb

$287 NZD per night

Guest favourite

Tiny home in Linville

4.99 out of 5 average rating, 604 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.

28 Aug – 4 Sep

$258 NZD per night

Guest favourite

Cabin in Vesuvius

4.91 out of 5 average rating, 293 reviews

Log Cabin on Pond & Mountainview

Enjoy the Meriwether Log Cabin nestled at the foot of the Blue Ridge Mountains with lovely views from the front porch, small pond out back and 2 minute hike to creek. Great for getaways, family gatherings with big deck & firepit to sit & enjoy nature. If you are a returning guest, please ask for our returning guest discount.

25 Jun – 2 Jul

$299 NZD per night