Family-friendly holiday rentals in Nellysford

5 out of 5 average rating, 220 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

4.96 out of 5 average rating, 742 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.

4.92 out of 5 average rating, 612 reviews

Farm stay in Nellysford

The Cottage at Spindle Hill: an Artist’s Farm

Relax and unwind in this fabulous handcrafted cottage— every detail has been considered! Beautiful mountain setting on small, historical farm just off Blue Ridge Parkway, the heart of Virginia wine country. Deep, hand-built cedar hot-tub. Minutes to the Appalachian Trail and Wintergreen resort. An easy walk to public trails, Devil's Backbone Brewery and Bold Rock Cidery. Beautiful gardens, hammocks, featured in design blogs. High-speed fiber internet. Library. Hens. Miniature Goats. EV Charger.

4.99 out of 5 average rating, 145 reviews

A three-story wooden house is nestled among lush greenery in a forested setting. The deck and patio area are accessible, surrounded by trees and natural landscaping, creating a serene environment for relaxation.

Home in Nellysford

Cabin Retreat | Family & Dog Friendly | Fire Pit

Welcome to the Wooder House, a cozy haven nestled in the woods of Virginia's beautiful Nelson County! Enjoy relaxing and connecting in a private home centered on 38 wooded acres, but close to NelCo fun! - Peaceful nature escape - Outdoor patio & fire pit - Great for families & dogs - Fully stocked kitchen - Private trail + hiking options nearby - 8+ min. to wineries, breweries, cideries, restaurants - 25 min. to Wintergreen Resort For more photos and fun, check us out on IG: @thewooderhouse

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, 213 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, 101 reviews

Home in Roseland

Stargazing on 12 Acres: Hot Tub 55"TV Fire Pit

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

4.96 out of 5 average rating, 241 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.

5 out of 5 average rating, 959 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, 312 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.

4.96 out of 5 average rating, 166 reviews

1 bedroom condo, walk to the slopes !

Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

4.89 out of 5 average rating, 152 reviews

The exterior of the farmhouse is highlighted, showcasing a charming structure with a red metal roof. Lush green bushes frame the gravel driveway, and trees provide shade in the background, enhancing the peaceful rural setting.

Guest suite in Roseland

Dogwood Suite at Open Heart Inn

Welcome to your country retreat! This unique section of the farmhouse was originally built in 1840, and features a cozy, king-sized bed. Relax on your private front porch, enjoy the views from the back patio, explore our 10 acres of farmland, take in the dogwoods and beautiful flowers, and get away from it all! Minutes from the Appalachian Trail, Devil's Backbone, and much more-- we are perfectly located to explore the trails, breweries, and wineries of scenic Nelson County.

4.92 out of 5 average rating, 624 reviews

An interior view showcases a cozy living space with wooden walls and ceiling, abundant natural light from large windows, and a ceiling fan. A gray sofa is complemented by a colorful throw blanket, while a small dining area with bright chairs is positioned nearby.

Guesthouse in Afton

Your Perfect Blue Ridge Mountain Hideaway near 151

A luxury tiny home built without compromise. This six-figure, custom-built retreat features high-end finishes, premium materials, and a refined layout that feels both elevated and comfortable. Set in the Blue Ridge Mountains, it offers privacy and tranquility with easy access to scenic drives, hiking, renowned breweries, and local wineries—ideal for a relaxed weekend escape focused on slowing down, good food and drinks, and returning home refreshed.

Popular amenities for Nellysford family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 241 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, 337 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!

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, 234 reviews

Ultimate cabin in the mountains

Cabin in Wintergreen Resort

The cabin's exterior is highlighted, showcasing a multi-level deck equipped with outdoor seating and a hot tub, surrounded by snow-covered trees. The natural landscape evokes a serene atmosphere, with the structure blending harmoniously into the winter scenery.

4.98 out of 5 average rating, 106 reviews

Wintergreen! Hot Tub, 2 Fireplaces, Arcade, Views

Home in Wintergreen Resort

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.

4.98 out of 5 average rating, 209 reviews

Hottub Ski InOut Renovated Chalet Lower Tyro Slope

4.87 out of 5 average rating, 255 reviews

A spacious bedroom features a king bed topped with a white duvet and a green accent blanket. A ceiling fan helps maintain a comfortable temperature. A mirror and a wall art piece add subtle decoration, while a bedside table with a lamp completes the inviting space.

Barn in North Garden

Barn Suite, Mountain View's & Hot tub! Pets OK

4.99 out of 5 average rating, 111 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!

4.94 out of 5 average rating, 125 reviews

A spacious deck features a hot tub and a dining area set for six. Scenic views of a vibrant sunset and surrounding landscape create a calming atmosphere, while the wooden decking enhances the connection to nature.

Home in Afton

Sycamore Shade: 151 House, HOT TUB, Mountain Views

Family- and pet-friendly home rentals

An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.

4.95 out of 5 average rating, 142 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

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, 334 reviews

Five Minute Walk to Everything!

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, 240 reviews

Eight Minute Walk to Everything

4.98 out of 5 average rating, 136 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 | Nelson 151

Superhost

The styled yome features a green roof and a circular structure, surrounded by trees. A wooden deck extends from the entrance, which includes a window. A fire pit with stones and a single grey chair are positioned in the foreground, set against a backdrop of autumn foliage.

Yurt in Afton

4.85 out of 5 average rating, 148 reviews

Yurt Off Grid Wood heat Getaway 70acre wooded farm

4.94 out of 5 average rating, 252 reviews

A cozy cabin constructed of logs stands among tall trees, with a small porch inviting guests in. An outdoor fire pit is situated nearby, surrounded by yellow seating. The gravel path leads to the cabin, showcasing a tranquil natural setting.

Farm stay in Esmont

Small cozy Cabin in the foothills! Dogs welcome!

4.84 out of 5 average rating, 113 reviews

Cottage in Afton

Artisan's Cottage: Woodsy+Private, Central to 151

Superhost

A charming cottage exterior is depicted, showcasing a white wooden facade with a blue roof. A patio area is furnished with a table and chairs under a green umbrella, surrounded by landscaped gardens and a pathway. Warm light is visible from the windows, suggesting a welcoming interior.

Cottage in Afton

4.87 out of 5 average rating, 621 reviews

Couples Getaway,heart of RT 151,stunning views

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, 240 reviews

The Modern Mountain Condo

Home in Wintergreen Resort

4.97 out of 5 average rating, 115 reviews

Cliffs Edge -A Contemporary Mountain Home

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

A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.

4.9 out of 5 average rating, 198 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

4.98 out of 5 average rating, 210 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!

A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.

4.97 out of 5 average rating, 160 reviews

2-min drive to slopes, stair-free/free firewood!

4.89 out of 5 average rating, 107 reviews

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.

Home in Nellysford

Mountain Bauhaus | Sleeps 8 | Amenities | Grill