Pet-friendly holiday rentals in Nellysford

4.97 out of 5 average rating, 152 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!

PetsOutdoor spacesParking

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, 276 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!

PetsOutdoor spacesLong stay

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, 181 reviews

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

Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

Outdoor spacesWalkabilityBathroom

4.97 out of 5 average rating, 259 reviews

An outdoor seating area features several Adirondack chairs arranged on a stone patio overlooking a wooded landscape, with bare trees extending toward the mountains in the distance. The communal game room includes a foosball table and a television mounted on a stone wall.

Cabin in Roseland

Gameroom~Mtn View~Fireplace~Main Level King~Grill!

The Blue Ridge Cabin is at the base of the mountain on the “151 Brewridge Trail”, just mins to wineries, breweries, hiking, skiing, golfing & lake fun. Experience a mountain vaca in this fun bear-themed cabin on 2 private acres, tucked away yet close to it all! Enjoy 12+ wineries & breweries within 15mins, 1/2 mi to Devils Backbone Brewery, 1 mi to Bold Rock Cider, 10 mins to Appalachian Trail, Shenandoah Nat. Park & Wintergreen Ski Resort! Charlottesville/Waynesboro 30mins. A perfect home base!

PetsWalkabilityBackyard

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.

4.98 out of 5 average rating, 191 reviews

Clean family-friendly 5br for wine country getaway

Come to Sunnyside! A new 5 bedroom home with game room, hot tub, and space for 12 people on 4 acres on a private farm road. Just off the infamous Route 151, or "Brew Ridge Trail", you are RIGHT in the middle of the action: 7 minutes to 10 wineries / breweries, 5 minutes to the nearest family farm or golf course, 10 minutes to Skyline Drive with PLENTY of places to hike, and 25 minutes to skiing at Wintergreen. You are surrounded by jaw-dropping mountain views/sunsets that surprise every guest.

PetsWalkabilityAccuracy

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

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.

PetsOutdoor spacesAir conditioning

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.

4.99 out of 5 average rating, 172 reviews

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!

WalkabilityOutdoor spacesBiking

4.92 out of 5 average rating, 641 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.

Outdoor spacesWalkabilityCheckout

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!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from Fire & Frost eatery and the Wintergreen Spa, this is an ideal location.

WalkabilityOutdoor spacesCheckout

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.

PetsOutdoor spacesSleep quality

4.96 out of 5 average rating, 384 reviews

The Brew Ridge Trail's Most Unique Home. Sleeps 12

"Guest Favorite" Top 5% of Homes on AirBnB. Rated 4.96★ by 100's of guests. Dogs welcome! 42x SuperHost property. Your Brew Ridge Trail Adventure starts here. Afton’s top-rated Airbnb, this bright, spacious 3,300 sq ft home was extensively renovated in 2026 with brand-new amenities. Minutes from Wintergreen, the Brew Ridge Trail, breweries, wineries, hiking, golf, and the Blue Ridge Parkway. Perfect for friend getaways, reunions, and unforgettable weekends.

WalkabilityOutdoor spacesCheckout

4.95 out of 5 average rating, 183 reviews

The exterior of a lakeside log cabin showcases a large, sloped roof with wooden beams and expansive windows. A spacious deck is visible, featuring various seating options. The structure combines natural stone and wood elements, reflecting a rustic yet modern aesthetic.

Cabin in Faber

Lakefront Cabin w Stunning Curated Decor & Hot Tub

✨ A Marvelous Night for a Moondance Awaits ✨ Welcome to Moondance—a lakeside log cabin with serious style and mountain soul. Designer interiors, cozy fireplaces, an après-ski game room, and dreamy views set the stage. Whether you're sipping wine on the deck or roasting s’mores under string lights, this is where memories are made. Minutes to wineries, Wintergreen, and the Blue Ridge Parkway. Relax, reconnect, and maybe do nothing at all. We support that.

Outdoor spacesWalkabilityLong stay

Popular amenities for Nellysford pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

4.88 out of 5 average rating, 527 reviews

Scenic Barn Escape on 151,Stunning views, Sleeps 6

Outdoor spacesPetsBathroom

4.99 out of 5 average rating, 313 reviews

Home in Tyro

Creekside Retreat | Fire Pit + Big Fenced Yard

WalkabilityPetsLocation

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, 168 reviews

Bear's Mountain Escape

PetsOutdoor spacesCleanliness

A functional kitchen with wooden cabinetry and an island is featured. The space includes a stove, modern appliances, and a ceiling fan. A brick wood stove adds a rustic element, while a small plant sits on the island, providing a touch of greenery.

4.94 out of 5 average rating, 162 reviews

Farmhouse on Working Vineyard

PetsOutdoor spacesHeating

4.96 out of 5 average rating, 130 reviews

The Branch at Afton Mountain Retreat

PetsWalkabilityWi-Fi

4.94 out of 5 average rating, 104 reviews

Designer Home w/ Incredible Views, Sleeps 16

PetsOutdoor spacesAccuracy

A cozy living space is highlighted by large windows that provide views of the surrounding trees. A comfortable sofa and armchair are arranged around a glass coffee table, complemented by a wooden dining set nearby. Warm wood accents are present in the ceiling beams and furnishings.

4.81 out of 5 average rating, 139 reviews

Cozy Mountain Home Nestled in Nature!

WalkabilityPetsFamily

A serene outdoor space features four wooden chairs arranged around a small fire pit. A hammock is nestled between trees in the background, offering views of the surrounding mountains and colorful autumn foliage. The lawn is dotted with fallen leaves, creating a tranquil atmosphere.

4.88 out of 5 average rating, 101 reviews

Mountain View Cottage | Wine, Hiking & Dog

PetsWalkabilityIndoor spaces

Pet-friendly home rentals with a pool

4.93 out of 5 average rating, 147 reviews

A rustic cabin is nestled among tall trees, with a wooden porch featuring natural wooden railings. The sun is seen setting through a light mist, casting a warm glow, while a gravel path leads to the driveway visible in the background.

Cabin in Nellysford

Cedar Base Camp

Outdoor spacesWalkabilityFamily

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, 149 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

PetsOutdoor spacesSkiing

The exterior view captures a two-story mountain condo, featuring a welcoming wooden ramp leading to a deck. The brown wood siding complements the natural surroundings, and multiple windows allow for ample light. Seasonal decor embellishes the entry, enhancing the inviting facade.

4.8 out of 5 average rating, 109 reviews

Your Cozy Mountain Getaway Awaits

Outdoor spacesPetsAir conditioning

4.95 out of 5 average rating, 200 reviews

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

PetsOutdoor spacesHospitality

A cozy living area features a teal sofa with a yellow accent pillow and a light wood coffee table. The kitchen is adjacent, showcasing modern appliances. Stairs lead to the loft bedroom. Artwork hangs on the wall, and natural light enters through high windows.

4.95 out of 5 average rating, 180 reviews

Ski-In Ski-Out ~ Mtn Views ~ King Suite

WalkabilityPetsAccuracy

Cabin in Wintergreen Resort

The exterior of the cabin is surrounded by trees, featuring multiple levels of outdoor decks. Large windows and sliding glass doors invite natural light into the interior. A cozy seating area is visible on the lower deck, providing a serene outdoor space.

4.92 out of 5 average rating, 100 reviews

Serene Wintergreen Retreat, Nestled in the Trees

WalkabilityPetsKitchen

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

Outdoor spacesPetsParks

A spacious great room features large windows, allowing natural light to fill the space while offering views of the surrounding trees. A comfortable sofa is positioned in front of a large television, and a dining table for eight is set nearby. Decorative accents include a chandelier and cozy armchairs.

4.95 out of 5 average rating, 110 reviews

Mntn View Pool Table Dogs OK Pool Tennis Golf Hike

WalkabilityPetsBarbecue

Private, pet-friendly home rentals

4.98 out of 5 average rating, 381 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

Outdoor spacesWalkabilityCheck-in

4.96 out of 5 average rating, 129 reviews

A colorful bedroom features a queen bed and a twin bed, both with patterned bedding. Walls are adorned with framed art, and windows are dressed with blue curtains. Warm lighting is provided by bedside lamps, creating a welcoming ambiance.

Guesthouse in Faber

Acorn Inn Cottage

Outdoor spacesPetsBreakfast

4.89 out of 5 average rating, 19 reviews

Cozy Wine Trail Cottage w/ Hot Tub & Fire Pit

Outdoor spacesAccessHospitality

5.0 out of 5 average rating, 36 reviews

Best Blue Ridge Views at Sunrise over Wintergreen

WalkabilityPetsGetting around

The exterior of a cozy modern cabin is visible, framed by lush greenery in the foreground. Fall leaves rest on the ground, while a flag hangs from the side of the home. Trees in vibrant autumn colors surround the cabin, enhancing the natural setting.

4.92 out of 5 average rating, 51 reviews

Cozy Modern Cabin near Wintergreen and Bold Rock

Outdoor spacesPetsComfort

4.99 out of 5 average rating, 86 reviews

Home in Roseland

Modern Farmhouse w/ Hot Tub, Yard. Pet Friendly!

PetsOutdoor spacesParking

A tranquil outdoor seating area showcases four wooden chairs arranged around a central gas fire pit. The backdrop features a breathtaking view of mountains and a colorful sky at sunset, surrounded by lush greenery. Gravel creates a rustic pathway beneath the seating.

4.96 out of 5 average rating, 55 reviews

Altitude Adjustment! Sauna and Wood Pizza Oven

Outdoor spacesPetsCheckout