Pet-friendly holiday rentals in Wintergreen Resort

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, 140 reviews

Close to skiing! | 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.

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, 226 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!

Flat in Wintergreen Resort

A balcony is featured, showcasing two Adirondack-style chairs positioned for optimal mountain views. Sunrise illuminates the expansive horizon, with soft light reflecting off the distant landscapes. The floor is made of wood, enhancing the outdoor ambiance.

4.99 out of 5 average rating, 103 reviews

Endless Mountain Top Views from All The Way Up!

Our warm and inviting condo combines amazing proximity to hiking with to-die-for views of the Blue Ridge Mountains and the horizon 75 MILES distant! Our condo sits a mere 400-yd walk from the closest hiking trail and also has direct access to the ridge line walking area - perfect place for a morning stroll! This updated and modern mountain themed space features: ✸ Newly renovated! ✸ Stocked modern kitchen! ✸ Two full bathrooms! ✸ Helix Hospitality Mattresses!! ✸ Cozy Fireplace w/ wood provided!

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.

4.95 out of 5 average rating, 327 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style master bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

A modern living area features a sleek leather sectional sofa adorned with patterned cushions, accompanied by a wooden coffee table. Large windows offer views of the surrounding trees, while natural light enhances the inviting space. A floor lamp adds illumination next to the sofa.

4.96 out of 5 average rating, 112 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

Charming 3-bedroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a new gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level

4.92 out of 5 average rating, 609 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.

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.

4.95 out of 5 average rating, 111 reviews

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10

We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

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

This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

4.98 out of 5 average rating, 208 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!

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.

4.87 out of 5 average rating, 609 reviews

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

Couples Getaway,heart of RT 151,stunning views

The Cottage is conveniently located along the Brew Ridge Trail. Sit on your patio and watch the sun set over Humpback rock and the Blue Ridge Mountains. Amazing location that’s set right in the middle of all the breweries. Spacious 6 acre farm with Route 151 road frontage. This handsome cottage is the perfect romantic get-a-way. Enjoy WiFi, air con, parking, self check-in and all the amenities you need to feel at home. Picturesque mountain views and beautifully landscaped grounds.

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.

4.97 out of 5 average rating, 144 reviews

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

Just steps from Wintergreen Resort’s slopes, Slope Side Gem offers the perfect mountain escape! Located in the heart of Mountain Village next to the Mountain Inn, you’re just a short walk to Starbucks, The Market, shops, and three restaurants and bars. Whether you’re skiing, hiking, golfing, or enjoying a local brewery or winery, adventure is at your doorstep. After an exciting day, unwind on the private balcony and take in the breathtaking mountain views!

4.92 out of 5 average rating, 275 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

The Humble Abode is a secluded CAMP & offers a scenic view of DePriest Mountains range and is the perfect place to un-plug & disconnect to reconnect!! Our private and secluded camp provides with spectacular mountain views and a NEW OUTDOOR Shower!! with pressurized ambient water temperature, spacious deck, covered porch, double bed, hammock, yard to play croquet/corn hole, private port-a-potty, charcoal grill, and a solo stove firewood pit.

Popular amenities for Wintergreen Resort pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An outdoor deck features a cozy fire pit surrounded by comfortable seating. The scene is tranquil with trees in the background, and a colorful sunset sky enhances the atmosphere. Soft lighting along the railing adds a welcoming touch.

5 out of 5 average rating, 36 reviews

4.97 out of 5 average rating, 141 reviews

The exterior of the house features a welcoming front porch with two chairs situated on a gravel path. Grass provides a lush green frame around the home, which includes a gabled roof and three dormer windows. A vibrant entry door adds a pop of color to the inviting façade.

Home in Nellysford

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

4.98 out of 5 average rating, 135 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

A comfortable gray sectional sofa is positioned near large windows, allowing natural light to brighten the space. Decorative throw pillows, including one with stripes, add subtle texture. A wooden side table holds a lamp, while a patterned area rug contributes warmth to the room.

4.96 out of 5 average rating, 132 reviews

Min to Wineries | Breweries | Restaurants | Trails

A living room is presented with a large, brown leather sofa in the foreground. An angular coffee table occupies the center, surrounded by two patterned armchairs. A television is positioned on a dark wood media console against a wall, with a potted plant adding a touch of greenery near a window dressed with light curtains.

4.96 out of 5 average rating, 260 reviews

CritzerHouse - on 151- Walk to the Brewery!

4.98 out of 5 average rating, 103 reviews

A wooden deck is adorned with hanging lights, providing a warm atmosphere. The scene captures a captivating sunrise over a range of mountains, with soft pastel colors illuminating the sky and the landscape below, showcasing the natural beauty of the surrounding area.

Home in Roseland

Book for Fall! Nelson 151, MTN views!

The exterior of a cozy two-story mountain house is visible, featuring brown wooden siding and large windows. Leaves cover the ground, and a gravel driveway leads up to the home, surrounded by trees displaying autumn foliage.

4.99 out of 5 average rating, 103 reviews

Cozy, relaxing mountain getaway on the golf course

The exterior of the two-story house is illuminated at dusk, showcasing a welcoming aesthetic. A circular stone fire pit is situated in the foreground, surrounded by landscaped gravel and rocks. A pair of chairs sits nearby, inviting relaxation by the fire.

4.98 out of 5 average rating, 131 reviews

Afton Home on 25 Acre Ridgetop with Amazing Views

Pet-friendly home rentals with a pool

An outdoor deck is equipped with a propane firepit surrounded by a dark block, offering a cozy gathering space. Comfortable, upholstered seating is arranged for relaxation, with expansive views of trees and hills in the background, showcasing the natural beauty of the mountainous landscape.

4.98 out of 5 average rating, 43 reviews

Stunning Views, Hot Tub, Impeccable Design

4.94 out of 5 average rating, 33 reviews

A warm and inviting living space features a stone fireplace with a fire glowing inside. A comfortable chair with patterned fabric sits beside a small glass coffee table. Natural light enters through large windows, creating a cozy atmosphere.

Home in Roseland

Hot Tub! Wintergreen Resort!

A spacious outdoor deck is surrounded by lush greenery, featuring a cozy seating area arranged around a fire pit. A private hot tub is visible on a raised platform, while the cabin showcases multiple levels of decks under a canopy of trees.

4.9 out of 5 average rating, 40 reviews

5 Min to Skiing! | Hot Tub • Firepit • Cozy Cabin

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.

4.93 out of 5 average rating, 152 reviews

Farmhouse on Working Vineyard

A spacious outdoor living area features a modern hot tub with glowing blue water, surrounded by a custom-built bar. Soft lighting from overhead lanterns adds a cozy ambiance, while a large screen TV is mounted nearby, overlooking the tranquil wooded surroundings.

5 out of 5 average rating, 44 reviews

Luxury Oasis|Family&Pets|Outdoor Lounge|Fire pit

Townhouse in Wintergreen Resort

The living area features a cozy red sofa and a wooden coffee table, complemented by a colorful area rug. A circular wooden dining table with four chairs sits nearby, illuminated by natural light from the large windows. A stone fireplace adds a rustic touch to the atmosphere.

4.94 out of 5 average rating, 198 reviews

Wintergreen home, ideal location, dogs welcome!

Flat in Wintergreen Resort

A panoramic view of rolling mountains is displayed under a colorful sky during sunrise. Soft clouds hover over the lush green hills, creating a serene landscape. The vast expanse of nature invites tranquility and offers a sense of openness.

5 out of 5 average rating, 11 reviews

Family and dog friendly with views and pools!

Cabin in Wintergreen Resort

The cabin features a warm wooden exterior with a red metal roof, set against a backdrop of lush greenery. A spacious front porch is presented, supported by wooden columns and adorned by wooden railing, inviting guests to enjoy the surrounding nature.

4.88 out of 5 average rating, 132 reviews

The Bear Dance Cabin at Wintergreen Resort

Private, pet-friendly home rentals

Two reclining chairs are positioned in a cozy living area, complemented by a warm orange wall. A dining area with a wooden table is visible in the background, along with large glass doors that provide natural light and access to a terrace overlooking greenery.

4.88 out of 5 average rating, 34 reviews

On the mountain, pet and child friendly

5 out of 5 average rating, 14 reviews

2 min to Slopes: Hot Tub, Gameroom, 3 King Beds

Cabin in Wintergreen Resort

An A-frame cabin is illuminated softly by string lights, showcasing a front deck that invites relaxation. Large windows reveal a warm interior, while the surrounding wooded lot creates a serene, natural setting at dusk.

4.98 out of 5 average rating, 82 reviews

On The Rocks

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.

4.99 out of 5 average rating, 99 reviews

The Cozy Cottage | Mountain views at Wintergreen

4.94 out of 5 average rating, 32 reviews

A spacious outdoor area is presented, featuring a fire pit surrounded by four adirondack chairs. Lush greenery and trees provide a serene backdrop, while the log cabin structure showcases a wooden porch that overlooks the natural landscape.

Cabin in Roseland

Secluded Log Cabin | Mtn Views | Pet-Friendly

A spacious deck features two lounge chairs and two wooden rocking chairs, offering a setting for relaxation. The surrounding area showcases lush green mountains under a clear blue sky, with expansive views of the valley below.

4.96 out of 5 average rating, 56 reviews

Mountain Homestead - Hottub, King, Dogs, Gameroom

4.91 out of 5 average rating, 70 reviews

The living room features a spacious sectional sofa and two armchairs, arranged around a wooden coffee table. A wood-burning fireplace is located against a green wall, complemented by softly illuminated shelves. Natural light filters through windows, creating a cozy atmosphere.

Apartment in Roseland

Nature’s Haven 1 Bedroom Condo Wintergreen Resort