Family-friendly vacation rentals in Nellysford

5 out of 5 average rating, 255 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

4.97 out of 5 average rating, 150 reviews

“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!

4.96 out of 5 average rating, 771 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.

A spacious dining area features a large wooden table set for twelve, surrounded by black chairs. A decorative light fixture hangs above, and a green accent wall complements the room. Shelving displays decorative items, adding character to the inviting space.

4.97 out of 5 average rating, 108 reviews

Twin Ponds | King Beds, Hot tub, Game Room, 75" TV

Welcome to Twin Ponds, a beautifully appointed & fun-filled mountain house in Wintergreen Resort's Stoney Creek just minutes from Rt 151’s breweries & wineries, golf, Lake Monocan, skiing, hiking & more. This 4-bedroom, 3.5-bathroom home features: - 3 king & 2 queen beds - Amazing Game Room w/ premium air hockey, ping pong, foosball, shuffleboard, board games, game table & 75" 4k Roku TV - Deck w/ 36" Blackstone flattop grill, gas firepit, cafe lights & hot tub We look forward to hosting you!

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, 227 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.

4.97 out of 5 average rating, 136 reviews

Home in Roseland

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

Relax with the family on 12 private acres at our peaceful, brand new construction farmhouse. We're just 12 miles to Wintergreen Ski Resort and Stoney Creek Golf, breweries, and wineries. Sleeps 8: K, K, Q + daybed w/ trundle. ★Amazing mountain views ★Hot tub for 6 people ★Outdoor shower ★Rockers, Adirondacks chairs for idle stargazing ★Gas grill ★Teak dining table seats 6 ★Indoor/outdoor gas fireplaces ★View 55” TV from comfy leather sofa/kitchen ★Pack 'n Play/Bassinet/High chair ★Mud room

4.95 out of 5 average rating, 282 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, 347 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.

4.92 out of 5 average rating, 639 reviews

Farm stay in Nellysford

Spindle Hill Cottage: an Artist’s Farm, Hot Tub

A handcrafted cottage on an artists' small, historic 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.

A hot tub bubbles invitingly on a concrete pad in a spacious yard. Surrounding the tub is a well-maintained green lawn, with majestic mountains visible in the background. White Adirondack chairs are positioned nearby for relaxing moments outdoors.

5 out of 5 average rating, 112 reviews

Game Room+Screen Porch+Hot Tub+Fire Pit on 151

Gather family & friends for a memorable getaway at The Myrtle at Wintergreen. This spacious golf-course retreat combines luxury, comfort and exceptional amenities minutes from Nelson 151 wineries, breweries, hiking, golf and Wintergreen Resort. 💦 Hot tub 🎱 Game room with pool, ping pong, foosball & air hockey 🛏️ Sleeps 10 with 2 Kings, 1 Queen & 2 Full (each with TV) 🔥 Screened porch, fire pit, BBQ ⚡ EV charger 🏊 Community pool, tennis & pickleball 🚗 40 minutes to Charlott

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.

4.97 out of 5 average rating, 156 reviews

Llama Loft | Fire Pit | Fenced Yard | Brew Trail

Escape to a spacious, colorful home off the Brew Ridge Trail with oversized windows, mountain views, and plenty of room for groups or couples. Cook in a stocked kitchen, then relax by the fire pit or grill out and unwind on the deck while the dogs enjoy the fenced in yard. Accessible bedrooms and bathrooms on the main floor make it easy for everyone to enjoy. Perfectly located near Wintergreen Resort, Skyline Drive, breweries, wineries, vineyards, hiking, biking, and golf.

4.99 out of 5 average rating, 375 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!

Popular amenities for Nellysford family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 180 reviews

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

Vacation 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, 275 reviews

Ultimate cabin in the mountains

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.

4.91 out of 5 average rating, 117 reviews

Hot Tub & Views | Mid Century Modern Wonder

4.99 out of 5 average rating, 155 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

Chalet in Wintergreen Resort

The main living area features a local stone fireplace framed by large windows that allow natural light to fill the space. A comfortable couch and wooden coffee table create a welcoming atmosphere, complemented by decorative pillows and a small potted plant on the table.

4.92 out of 5 average rating, 130 reviews

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

5 out of 5 average rating, 997 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

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, 238 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

4.98 out of 5 average rating, 191 reviews

The two-story house features a white exterior with dark shutters and a welcoming front porch. A gently sloped lawn surrounds the home, leading to mature trees and a scenic backdrop. The roof is accented with three gabled dormer windows, adding character to the facade.

Home in Afton

Clean family-friendly 5br for wine country getaway

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 163 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

4.94 out of 5 average rating, 100 reviews

Pickleball | 2 Homes | Sleeps 19 | 151 Brew Trail

4.99 out of 5 average rating, 206 reviews

An interior view of the yurt features a circular ceiling with a skylight. Light wooden beams create a warm atmosphere. A kitchenette with a granite countertop is visible on the left, while a cozy seating area with a blue couch and decorative accents is displayed on the right. Natural light fills the space.

Yurt in Roseland

Mtn View~Firepit-Bold Rock & DB 2mi~Nat. Park 10mi

A dining area features a rustic wooden table surrounded by modern chairs. Large glass windows showcase panoramic mountain views, while natural light illuminates the space. A stylish floor lamp adds warmth, complementing the cozy décor of the nearby seating area.

4.98 out of 5 average rating, 109 reviews

The Cozy Cottage | Mountain views at Wintergreen

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, 167 reviews

Bear's Mountain Escape

4.98 out of 5 average rating, 229 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.

Apartment in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

4.98 out of 5 average rating, 380 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

4.88 out of 5 average rating, 527 reviews

The exterior of a charming white building is shown, characterized by sleek lines and stone accents. Symmetrical windows allow natural light to enter, while greenery provides a pleasant contrast against the structure. A gravel pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Afton

Scenic Barn Escape on 151,Stunning views, Sleeps 6

Family-friendly home rentals with a pool

Condo in Wintergreen Resort

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, 254 reviews

Where the Trail Ends

4.97 out of 5 average rating, 128 reviews

Cliffs Edge -A Contemporary Mountain Home

4.97 out of 5 average rating, 119 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

Condo in Wintergreen Resort

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, 253 reviews

Eight Minute Walk to Everything

The open living area features high ceilings and large windows, allowing natural light to enhance the space. A comfortable seating arrangement includes a sofa and two armchairs, while an adjoining kitchen is visible in the background, equipped with modern appliances.

4.89 out of 5 average rating, 130 reviews

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

Condo in Wintergreen Resort

4.97 out of 5 average rating, 180 reviews

Extremely private, HOA pool/stair-free entry

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, 148 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10