Family-friendly vacation rentals in Waynesboro

4.98 out of 5 average rating, 299 reviews

The cottage is framed by lush greenery and trees, showcasing rustic wooden siding and a steeply pitched roof. Large windows allow natural light to fill the interior. A pair of rocking chairs is situated on the porch, inviting relaxation in a serene outdoor setting.

Cottage in Afton

Oasis in the Blue Ridge Rt. 151 Brew Ridge Trail

Welcome to the Glass Hollow Cottage! Come make yourself at home and enjoy the rustic charm of our custom hand-built cottage. A perfect getaway for a couple or friends who want a 1-of a-kind destination. Adventure and R & R await you!!! Enjoy the well stocked kitchen & the bright, clean, cheery ambience.... everything you need to feel at home & then some. Prime location: Just minutes to Rt. 151/Brew Ridge Trail, dozens of popular wineries/breweries, Wintergreen Resort & Shenandoah Nat. Park.

4.99 out of 5 average rating, 155 reviews

A firepit area features several Adirondack chairs arranged around a sandy circle. Natural rock formations and a lush tree line create a serene backdrop, framed by expansive mountain views in the distance.

Chalet in Afton

Elk Mountain Overlook: Breathtaking Views

Mountaintop overlook with jaw dropping views and camp themed interior design. Perched upon Elk Mountain just off the Blue Ridge Parkway this petite chalet is under 30 min from Charlottesville, 10 min to 151 vineyards/breweries/cideries, and 10 min to Waynesboro. Relax in this natural retreat featuring 2 king bedrooms, 2 person soaker tub, double headed shower, and ample kitchen w/many extras. Take in the views from the large deck, firepit, under porch swing, or mountainside adirondack chairs.

Guest suite in Waynesboro

A spacious front porch is adorned with vibrant flowers in various shades, creating a welcoming environment. Comfortable seating is arranged to invite relaxation, while lush greenery provides an enhanced view of the surrounding area. A patterned outdoor rug complements the serene setting.

4.98 out of 5 average rating, 397 reviews

The LoriAnn, A Boutique Stay New Sleep Number Bed

This beautifully restored 1940’s home in the City of Waynesboro is just a short drive from the Blue Ridge Parkway. Modern amenities, light complimentary breakfast items and assurance of comfort awaits! Enjoy one of a kind Autographed Movie and TV Memorabilia. The spacious front porch is yours to enjoy including a 100 yr old porch swing that belonged to my Great Grandmother. Along with the Parkway & Skyline Drive, enjoy Restaurants, Breweries, Vineyards, movie theaters and exploring Route 151.

4.99 out of 5 average rating, 102 reviews

The unique octagonal house is framed by lush greenery, showcasing its distinctive architecture. A spacious deck offers a vantage point for enjoying unobstructed views of the surrounding landscape. Panoramic windows reflect the natural beauty of the Blue Ridge Mountains, inviting light into the living space.

Home in Afton

Mountain Overlook House - Blue Ridge Parkway

Unique octagonal house with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.

5 out of 5 average rating, 981 reviews

A serene landscape showcases rolling hills adorned with autumn foliage. In the foreground, tall grass and scattered trees lead to a cozy house perched on a hillside, surrounded by vibrant fall colors. The distant mountains create a peaceful backdrop.

Yurt in Afton

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

Experience glamping, Blue Ridge style. Our luxury yurt is located at the top of a small hill, in the center of a 70 acre farmstead surrounded by natural beauty. Night Archer Farm is located off a quiet country road in Afton, Nelson County. It is private, but not remote. You are close to the Brew Ridge trail, wineries, breweries, skiing at Wintergreen, Blue Mountain Brewery, Devil's Backbone, golf, hiking, or driving the Blue Ridge Parkway. Hike directly from the Yurt up into the mountains!

4.99 out of 5 average rating, 334 reviews

Four horses graze on a lush green lawn, with a charming two-story building in the background. The house features a balcony and is surrounded by blooming shrubs and trees, creating a serene atmosphere on the farm.

Farm stay in Afton

Afton, Mountain View Mini Farm

Welcome to Mountain View Mini Farm! We are located in the Rockfish Valley(Afton, VA)with amazing views of the Blue Ridge Mountains. Our farm is just minutes to wineries, breweries, cideries, Shenandoah National Park and more! There is so much to do close by, but once you get on the farm, you won't want to leave! We have a total of 5 horses, with 3 being mini rescue horses. There's a fire pit area where you can roast S'mores while you watch the sunset. Be sure to look at bedrm 2 description.

4.99 out of 5 average rating, 244 reviews

A charming bungalow exterior is showcased, featuring a wraparound porch with seating. Surrounding greenery, including bushes and grass, enhances the outdoor appeal. The structure is painted in a dark hue with wooden accents, complementing the clear blue sky.

Bungalow in Afton

The Bungalow at Afton Mountain Retreat by Veritas

Welcome to The Bungalow at Afton Mountain Retreat in the heart of Brewery Trail/Route 151, Vineyard country and the foothills of the Blue Ridge Mountains. The Bungalow is located 1/4th mile from Veritas Vineyard. It is within 10 minutes to every brewery, vineyard, distillery and cidery along Route 151 Crozet, 1 mile from the newly opened Blue Ridge Tunnel and 20 minutes to Wintergreen Resort for winter fun! Completely remodeled and ready to spoil the best guests who simply want to unwind.

4.89 out of 5 average rating, 326 reviews

The exterior of the cottage features a welcoming porch with two seated chairs and a wooden railing. Lush greenery and trees surround the cottage, complemented by a beige wooden fence that offers privacy. A clear blue sky brightens the scene, enhancing the inviting atmosphere.

Bungalow in Waynesboro

The Copper Cottage - near the Appalachian Trail

An antique fully renovated, cozy cottage that blends the character of saw milled wood beams, hand-crafted finishes, & local art with the modern comforts of Wi-Fi, Streaming TV, A/C, and a Jetted shower that might raise your attitude with the altitude! At the entrance to downtown Historic Waynesboro and the riverside park, its restaurants and stores can entertain even the peculiar palate or collector, some are right across the street! Fully fenced in back yard, so bring the pups to play!

4.97 out of 5 average rating, 112 reviews

A compact living area features a cozy seating arrangement with a sofa and a daybed adorned with vibrant cushions. Large windows provide ample natural light and views of the surrounding greenery. A well-equipped kitchenette is visible, complete with a sink and modern appliances.

Tiny home in Afton

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

Welcome to Rusty's Retreat, conveniently located just off Va's famous Brew Ridge Trail. Small space, big comfort. This brand-new luxury tiny home is thoughtfully designed with modern finishes, high-end amenities, and a surprisingly spacious feel. Set in the Blue Ridge Mountains, it offers total privacy and easy access to local breweries, wineries, and scenic drives. Perfect for couples or solo travelers seeking a quiet, stylish escape close to great drinks, views, and adventure.

4.99 out of 5 average rating, 372 reviews

Cabin in Vesuvius

The Sanctuary

Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

4.99 out of 5 average rating, 442 reviews

The cottage is framed by tall trees and lush greenery. It features a welcoming front porch with wooden posts, surrounded by well-maintained grass. A glimpse of a rustic barn is visible in the background, adding to the serene farm setting.

Farm stay in Weyers Cave

FarmCottage: Hot Tub Sauna Massage ShenandoahViews

Welcome to the Cottage at Dices Spring Farm. This gem is nestled in the beautiful Shenandoah Valley. You will love the weather-sheltered hot tub building, relaxing greenhouse garden massage space and personal finely crafted sauna with a Sweden built cold shower dump bucket A custom bathroom double-headed shower, and reading nook in the loft are favorites to unwind and disconnect. Minutes away from JMU, Buc-ee's, Valley Pike Market & Vineyards.

4.93 out of 5 average rating, 376 reviews

A charming white bungalow is shown, featuring a welcoming yellow front door and dark shutters. Sunlight filters through the trees, highlighting the neatly landscaped front yard and walkway leading to the entrance.

Bungalow in Waynesboro

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Enjoy the entire home to yourself, including a relaxing backyard retreat with hot tub. Perfect for singles or couples who want to stay home and relax or visit the sites then come home to enjoy the hot tub under the stars. 10 min drive to shopping; 10 min to Blue Ridge Parkway & Skyline Drive; 15 min to 151 Breweries. kayaking/canoeing/hiking/fishing on the beautiful South River.

Popular amenities for Waynesboro family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 204 reviews

A welcoming porch area features wooden decking with rustic chairs, inviting relaxation. Natural light streams through a nearby arched window, and the surrounding landscape showcases trees and hills in the distance, creating a serene outdoor environment.

Dome in Stanley

Secluded LUX Bunker | Hot Tub, Views & Trails

Treehouse in Stanardsville

4.97 out of 5 average rating, 104 reviews

CloudPointe Retreat

4.93 out of 5 average rating, 251 reviews

An open-concept living area features high vaulted ceilings with exposed wooden beams. A cozy seating arrangement is positioned around a fireplace, with a contemporary dining table nearby. Large windows allow natural light to fill the space, showcasing views of the surrounding outdoor landscape.

Cabin in Faber

Modern cabin, hot tub, mtn views, fireplace

4.92 out of 5 average rating, 189 reviews

The exterior of the retreat features large glass windows, providing an open view of the surrounding landscape. A spacious deck includes two black Adirondack chairs and a private hot tub, set against a backdrop of mountains and a colorful sunset.

Cabin in Shenandoah

Blue Ridge Retreat 2 w/ Hot Tub/Sauna/Cold Plunge!

4.97 out of 5 average rating, 118 reviews

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

Home in Afton

Perfect getaway among the orchards of Batesville

4.88 out of 5 average rating, 123 reviews

A spacious outdoor seating area features six Adirondack chairs arranged around a stone fire pit. The structure's deck extends above, blending into the green landscape that includes trees and grass, with a backdrop of gentle hills under a partly cloudy sky.

Home in Afton

Fox Hill: Hot Tub, Views, Pet Friendly!

4.87 out of 5 average rating, 376 reviews

A private hot tub is illuminated at night, inviting relaxation. Nearby, a fire pit surrounded by Adirondack chairs offers a cozy seating area. The cabin is visible in the background, with warm lights visible through the windows and string lights creating a gentle glow among the trees.

Cabin in Shenandoah

HyggeCabin•Hot Tub, Firepit, Mountain Getaway

Earthen home in Stanardsville

The hobbit house features a distinctive curved roof covered with greenery, enhancing its natural appearance. Large windows framed by wooden arches provide ample light, while the stone exterior blends seamlessly with the surrounding landscape of trees and grass.

4.86 out of 5 average rating, 287 reviews

Hobbithouse at White Lotus Eco Spa Retreat

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 101 reviews

A modern kitchen features light-colored cabinetry and open shelving. A stainless steel refrigerator and dishwasher are visible, alongside a double sink beneath a window. A round glass dining table is set with black chairs, while decorative items and utensils are neatly arranged on the shelves.

Home in Staunton

Queen City Cottage - Walk Downtown

4.87 out of 5 average rating, 505 reviews

The exterior of a cozy, white house is surrounded by lush greenery. A covered porch is visible, along with colorful outdoor seating. Warm string lights hang above the outdoor area, inviting relaxation and enjoyment of the natural surroundings.

Cottage in Afton

GreenHouseNelson

4.92 out of 5 average rating, 122 reviews

A custom-built tiny house features a sleek black exterior set against a vibrant blue sky with scattered clouds. The structure is surrounded by grassy areas and decorative stone, with a wooden fence partially visible in the background, enhancing the natural landscape.

Tiny home in Afton

Cozy Modern Tiny Home, Mountain Views, Sleeps 2

4.97 out of 5 average rating, 145 reviews

The exterior view showcases a modern blue house set against a backdrop of lush green hills. A wooden deck extends from the home, providing access to outdoor space. The gravel driveway is lined with a rustic split-rail fence, enhancing the natural feel of the surroundings.

Home in Nellysford

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

4.89 out of 5 average rating, 281 reviews

The Carriage House is viewed from the yard, emphasizing its white exterior and green roof. The screened porch is visible, surrounded by natural landscaping, including grasses and bushes. Tall trees form a backdrop, contributing to the tranquil setting.

Cottage in Crozet

The Carriage House

4.93 out of 5 average rating, 221 reviews

A comfortable living area is furnished with a dark sofa adorned with textured cushions. Two light-colored armchairs are positioned nearby, and a small side table holds a plant. Natural light floods the space through large windows, illuminating the patterned area rug.

Apartment in Staunton

Traveler’s Escape-1 bedroom. Walk to downtown!

4.83 out of 5 average rating, 531 reviews

The open living area features a dining table with wooden finish surrounded by blue chairs. A comfortable couch is positioned nearby, and a TV sits atop a low table. Natural light floods in through multiple windows, illuminating light-colored walls and a patterned rug.

Chalet in Afton

Chalet house next to wineries/breweries!

4.99 out of 5 average rating, 221 reviews

The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.

Cabin in Free Union

Shenandoah Stargazer with Sauna

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 216 reviews

Cabin in Dayton

Luxurious Cabin By the Creek! Inground pool! Spa!

5 out of 5 average rating, 104 reviews

A bright game room features a blue pool table at the forefront, surrounded by a variety of games like foosball and air hockey. Comfortable seating is arranged near large windows, allowing natural light to fill the space. Tall bar stools add extra seating options.

Home in Nellysford

Family Fun on 151: Game Room+Screen Porch+Hot Tub

4.96 out of 5 average rating, 236 reviews

A private in-ground swimming pool is surrounded by a wooden deck and sun loungers. Shade is provided by a canopy, and lush greenery is visible in the background, highlighting the calming outdoor setting. The pool features a net for recreational activities.

Home in Lovingston

Private Pool Opens April 1 - All Year Hot Tub

4.96 out of 5 average rating, 109 reviews

A spacious yurt is surrounded by lush greenery, with trees framing its exterior. The entrance is marked by a set of steps leading up to the door. Natural stone borders the well-maintained pathway, enhancing the connection to the countryside.

Yurt in Afton

Mountain View Getaway Yurt

4.98 out of 5 average rating, 159 reviews

The entrance to Fairhill Farm is marked by a white wooden sign displaying the name, set against a backdrop of rolling hills adorned with autumn foliage. A vibrant red bush frames the sign, contributing to the natural beauty of the landscape.

Home in Stanardsville

Farm Cottage w. Blue Ridge views 20 mins from SNP

Farm stay in Barboursville

Two goats are seen in a grassy area, one with distinctive black and white fur and prominent horns, while the other has a mainly white coat. A chicken is visible nearby, contributing to the lively farm environment.

4.96 out of 5 average rating, 245 reviews

Moonfire Farm cozy Shenandoah Region Getaway

4.96 out of 5 average rating, 1,279 reviews

A round green yurt stands surrounded by a grassy area, accented by a flower bed of daffodils in bloom. A wooden deck leads to the entrance, while a fire pit with log seating is positioned nearby. Bare trees provide a serene mountain backdrop.

Yurt in Stanardsville

Yurt*FARM*horses*goats*woods*STARS*Hotub*Hiking