Family-friendly holiday rentals in Nellysford

Holiday home in Lovingston

The cabin's exterior is surrounded by lush greenery, featuring a spacious porch with seating and a hot tub nearby. The two-story structure is constructed of wood, with large windows allowing natural light to fill the interior. A picnic table is located in the yard.

4.96 out of 5 average rating, 255 reviews

Ultimate cabin in the mountains

This unique and secluded cabin sits on 75 acres in the Blue Ridge mountains. Enjoy the cozy wood fireplace, hot tub, charcoal grill, and fast, reliable fiberoptic internet if you need to get some work done while you're away. It has a washer and dryer, a full kitchen, and is pet-friendly (no pet fee!), so you can enjoy it with the whole family. There is a 4K 55” smart TV with apps, a Tesla LVL 2 charger, a cabinet full of board games, books, and plenty of items to entertain both kids and adults!

4.97 out of 5 average rating, 143 reviews

Home in Nellysford

“Small" House/Peaceful/Brewery/Hike/Winery/River

The Small House is anything but small when it comes to comfort and relaxation. Located in the heart of Nellysford near a local grocery store and restaurants. Close to many hikes, the Blue Ridge Parkway, the AT, wineries, cideries, and breweries! The property includes a deck, outdoor fire pit, grill, and 11 acres to explore. At the very back of the property is 600 feet of private river/creek access. The perfect spot to fish, picnic, and/or let the kids and pups cool off and play! Come and stay!

5 out of 5 average rating, 235 reviews

A cozy cottage, named the 'Sugah Shack,' is nestled amidst the rolling hills of the Blue Ridge Mountains. The white exterior contrasts with the vibrant greenery surrounding the property, while the majestic mountains form a picturesque backdrop against a bright, partly cloudy sky.

Cottage in Afton

Cozy Mountain Cottage on Brew/Wine Trail-King Bed

Welcome to the Sugah Shack, a cozy, beautifully appointed new construction cottage nestled in the foothills of the Blue Ridge Mountains! Located midway on the Brew Ridge Trail, but 500 yards off the byway, so guests have a quiet retreat. Perfect for romantic getaways, destination telework space, or families exploring this outdoor paradise community. Stunning property boasts beautiful vistas with sweeping 300-degree mountain and a year-round calendar of outdoor activities. GAS FIREPLACE/FIREPIT

5 out of 5 average rating, 154 reviews

A charming cottage is nestled among lush green grass and surrounded by trees. Its metal roof and white siding are complemented by well-maintained shrubbery. Dappled sunlight filters through the tree branches, creating a serene outdoor ambiance.

Cottage in Covesville

Historic cottage with stunning mountain views

Welcome to Rose Cottage in picturesque Albemarle County, where you'll enjoy expansive 360-degree views of the mountains surrounding historic Cove Lawn Farm. Relax in the tranquil rural setting or stroll more than two miles of comfortable walking paths that wind through 25 acres of stream-lined hayfields. From Rose Cottage, you're just minutes from the best local cideries, distilleries, and wineries including Pippin Hill Farm & Vineyards. Easy 20-minute drive to UVa and 22 minutes to Monticello.

4.96 out of 5 average rating, 755 reviews

The gravel pathway leads to a charming log cabin, framed by tall trees and surrounded by greenery. A sign reading 'COZY MOUNTAIN CABIN' is positioned near the path, inviting visitors to explore this secluded retreat in the Blue Ridge.

Cabin in Roseland

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.

4.99 out of 5 average rating, 144 reviews

An inviting outdoor space features a hot tub surrounded by a spacious deck, with mountain views in the background. A large dining table with wooden chairs is positioned indoors, complemented by a fully-equipped kitchen visible in the adjacent area. A cozy fire pit with adirondack chairs provides a warm setting.

Home in Afton

Hot Tub, Firepit, Mtn Views, Walk to Coffee & Park

Welcome to Creekside! Just minutes from the best wineries and breweries, it’s the perfect getaway to explore the 151 Brew Trail, Wintergreen Resort and the Blue Ridge Parkway. Enjoy mountain views and privacy in the hot tub. Roast marshmallows around the huge fire pit. Cozy up on the sectional sofa in front of the 65" 4K TV. Cooks will enjoy the spacious and fully equipped kitchen! All beds have premium memory foam mattresses. Fast Wi-Fi for remote work! Level 2 EV charger located in driveway.

Guest suite in Nellysford

A scenic view captures a small orange plane flying above a grassy field, framed by distant mountains under a clear blue sky. Hay bales are scattered throughout the field, and trees provide a natural boundary along the scene.

4.98 out of 5 average rating, 220 reviews

Wintergreen Bunkroom Private Suite BEST Location

Wintergreen Resort, (4.6 mi) Bold Rock Cider (1/2 mile/walking distance) Devil’s Backbone, Blue Toad Cider. Hazy Vineyard. Blue Mountain Brewery. Veritas Vineyard. Afton Mountain Vineyard. Rockfish Glider Port (backyard) Off 151, in Nellysford. Attached suite, PRIVATE entrance & bath, self check in. NOT a shared space with owner. 2 rooms sleep 6 MAX. Bunkroom sleeps 4, living room sleeps 2 on sofa bed. Clean and sanitized to standards. Microwave, mini fridge, wet bar. NOT a full house rental.

4.96 out of 5 average rating, 258 reviews

The interior of the tiny house features an open kitchen layout with modern appliances and a central island. A geometric area rug extends across the floor, while light wood accents create a warm feel. Shelving holds books and decor, enhancing the cozy atmosphere.

Cabin in Nellysford

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.

4.99 out of 5 average rating, 328 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, 162 reviews

A spacious deck is surrounded by greenery, featuring several black Adirondack chairs arranged around a firepit. The glass railing provides an unobstructed view of the outdoors, enhancing the inviting outdoor space.

Home in Nellysford

151Escape | 5☆ Group Fun! Game Room/Bar/Deck/4kTVs

Enjoy mountain adventures with friends & family at this beautiful & newly renovated 5 bedroom mountain house ideally located in Virginia Wine Country at Wintergreen Resort’s Stoney Creek valley area. This amazing home features: - 75” & 55” 4k TVs - Fully equipped, live edge wet bar & bar countertop - Professional Ping Pong table - Deck with views, firepit & grill Just minutes from skiing, golf, hiking, wineries, breweries, apple-picking and other adventures the area offers all year long!

4.92 out of 5 average rating, 624 reviews

Farm stay in Nellysford

The Cottage at Spindle Hill: an Artist’s Farm

A handcrafted cottage on a small, historic artist's farm, built of salvaged materials and sustainably forested Virginia timber — featured in design blogs, stocked with genuine care, and unlike anything else you'll find. Cedar hot tub. Record player. Fresh eggs. Homemade granola. Beautiful gardens, hammocks, and a 200-year-old White Oak. Minutes to Devils Backbone, Bold Rock, the Blue Ridge Parkway, and the Appalachian Trail. High-speed fiber. Library. Hens. Miniature Goats. EV Charger.

4.97 out of 5 average rating, 104 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.

Popular amenities for Nellysford family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 118 reviews

Home in Roseland

Stargaze on 12 Acres: Hot Tub 55"TV Fire Pit Grill

A welcoming living area features two leather couches arranged around a wooden coffee table, which is complemented by a patterned rug. Large windows allow natural light to illuminate the space, offering views of the surrounding trees. Sliding glass doors provide access to an outdoor deck.

4.99 out of 5 average rating, 162 reviews

Close to hiking! | King Beds | Fireplace | Hot Tub

The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.

4.89 out of 5 average rating, 155 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

4.96 out of 5 average rating, 233 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

Cabin in Wintergreen Resort

The exterior of the mountain home showcases a mid-century modern design, with large windows surrounded by trees displaying autumn colors. A spacious deck features seating areas and a fire pit, inviting gatherings. Soft lighting highlights the outdoor space, enhancing the connection with nature.

4.9 out of 5 average rating, 110 reviews

Hot Tub & Views | Mid Century Modern Wonder

A spacious bedroom features a high, wood-beamed ceiling and a large window providing natural light. The bed is dressed in navy bedding with a plaid blanket draped across it. A wooden dresser and lamp complement the rustic decor, and a mounted TV is positioned above.

4.97 out of 5 average rating, 225 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

Villa in Wintergreen Resort

A spacious living area is highlighted by large floor-to-ceiling windows, offering views of the surrounding trees. A comfortable gray sofa and a round glass coffee table are present, along with a wooden dining table that seats six. An electric fireplace adds warmth to the space.

4.96 out of 5 average rating, 133 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

4.99 out of 5 average rating, 118 reviews

A serene view of the Blue Ridge Mountains is presented, showcasing rolling hills blanketed in mist during sunrise. The sky is painted with soft pastel shades of orange and pink, highlighting the natural beauty of the surrounding landscape.

Home in Afton

Mountain Mama- Amazing Views! + Hot Tub!

Family- and pet-friendly home rentals

The exterior of a two-story cabin houses warm wooden accents and large windows. The entrance features a welcoming set of wooden steps leading up to a balcony, surrounded by tall trees, with a concrete pathway leading toward it.

4.94 out of 5 average rating, 247 reviews

Eight Minute Walk to Everything

4.98 out of 5 average rating, 200 reviews

A bright living area features large windows providing ample natural light. A light-colored sofa is paired with two blue armchairs and a circular coffee table. Nearby, a television is positioned against a wall adorned with framed artwork, seamlessly connecting to the kitchen area.

Cottage in Nellysford

Rockfish Valley Cottage

4.99 out of 5 average rating, 490 reviews

A tiny house is set against a backdrop of colorful sunset skies. The exterior features blue siding with softly glowing lights around the entrance. Lawn chairs are positioned in front, inviting relaxation. Trees and greenery surround the area, enhancing the serene atmosphere.

Tiny home in Scottsville

Rare Find: Private Animal Sanctuary & Tiny Cottage

4.99 out of 5 average rating, 893 reviews

A charming cottage with a peaked roof features a welcoming red door. Surrounding gardens with colorful flowers and lush greenery enhance the entryway, while a gravel path leads to the entrance. Trees provide a natural backdrop, contributing to the serene setting.

Home in Keswick

Charming Cottage at Golden Hill

4.98 out of 5 average rating, 220 reviews

A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

4.99 out of 5 average rating, 210 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

4.98 out of 5 average rating, 362 reviews

A large window offers a panoramic view of vibrant autumn foliage, displaying various shades of orange, yellow, and red across rolling mountains. The scene is framed by a wooden railing, enhancing the connection to nature.

Cabin in Tyro

Tyro Mountain View Cabin

4.92 out of 5 average rating, 283 reviews

A rustic exterior of the camp is shown, featuring wooden siding and a sloped roof blanketed in snow. Snow rests on the overhang, while a set of wind chimes hangs near the window, overlooking the distant DePriest Mountains, partially veiled by a winter mist.

Tiny home in Roseland

The Humble Abode Camp

Family-friendly home rentals with a pool

A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.

4.93 out of 5 average rating, 253 reviews

The Modern Mountain Condo

4.93 out of 5 average rating, 233 reviews

The exterior of Pine Lake Lodge is displayed, featuring a stone chimney and a covered porch with several chairs. Lush green grass surrounds the lodge, complemented by trees and colorful foliage in the background, creating a serene outdoor setting.

Home in Charlottesville

Pine Lake Lodge

4.96 out of 5 average rating, 106 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

The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.

4.96 out of 5 average rating, 350 reviews

Five Minute Walk to Everything!

Superhost

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.

Farm stay in Barboursville

4.95 out of 5 average rating, 244 reviews

Moonfire Farm cozy Shenandoah Region Getaway

A wooden walkway leads to the entrance of the house, framed by vibrant pink rhododendron flowers. Tall trees provide a natural backdrop, with dappled sunlight filtering through the leaves, creating a serene outdoor setting.

4.95 out of 5 average rating, 149 reviews

Bear's Mountain Escape

4.95 out of 5 average rating, 197 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!