Family-friendly vacation rentals in Waynesboro

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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

Guest suite in McGaheysville

4.98 out of 5 average rating, 420 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+!

Nov 29 – Dec 6

€ 83 per night

Guest favorite

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!)!

Aug 17 – 24

€ 152 per night

Superhost

Cabin in Buckingham

4.91 out of 5 average rating, 175 reviews

Lotus View Retreat in Yogaville / Cabin

Beautiful Log Cabin with a separate bedroom with queen-size bed, and a sleeping/meditation loft, full kitchen, full bath, a semi-wraparound deck and a covered porch. The cabin deck is excellent for star gazing on the clear night sky There is a laundry machine available for stays longer than 5 days. The oven is temporarily out-of-service but if you need access to one please let me know and we can arrange for that. The stovetop has a substitute double burner hot plate for the time being.

Dec 26 – Jan 2

€ 120 per night

Guest favorite

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.

Aug 3 – 10

€ 121 per night

Guest favorite

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.

Apr 6 – 13

€ 162 per night

Guest favorite

Cabin in Roseland

4.96 out of 5 average rating, 653 reviews

Cozy Mountain Cabin

Snuggled in the Blue Ridge. Secluded from the crowds. Experience your visit in an authentic log cabin. Perfect romantic getaway or personal retreat. Less than 2 miles to Devil's Backbone and Bold Rock. Minutes from the Appalachian Trail, Wintergreen 4-Season Resort, many breweries, wineries, cideries, restaurants, horseback riding, hiking trails, outdoor concerts, and antique shopping. Complimentary hot cocoa, tea, coffee, popcorn. High-speed internet, SMART TV. Air Conditioning.

Nov 2 – 9

€ 131 per night

Guest favorite

Tiny home in Charlottesville

4.94 out of 5 average rating, 668 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.

Feb 24 – Mar 3

€ 121 per night

Guest favorite

Cabin in Faber

4.98 out of 5 average rating, 138 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.

May 24 – 31

€ 170 per night

Guest favorite

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.

Sep 30 – Oct 7

€ 113 per night

Guest favorite

Apartment in Weyers Cave

4.93 out of 5 average rating, 241 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.

Jun 23 – 30

€ 106 per night

Guest favorite

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!

Jan 1 – 8

€ 157 per night

Guest favorite

Farm stay in Crozet

4.95 out of 5 average rating, 154 reviews

Refreshed '24, Mt Views & Pool: Sunset Farm Studio

2024 Upgrades! Sunny, spacious Q bed/living room upstairs (wood stove); mini-kitchen & bath downstairs on a 10-acre farm with 180-degree views of Blue Ridge Mts. A floor mattress is available for an extra fee. Quiet, private, big-sky, 5 min from Crozet. I have a blind dog; no visitor dogs. It is a perfect place to be on retreat/ wine country or get work done (WiFi and a printer). NEW 50" TV.

Sep 20 – 27

€ 156 per night