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, 152 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.

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.

4.94 out of 5 average rating, 142 reviews

Bear's Mountain Escape

Dog friendly, 3 BR, 2 BA, loft style condo located in the heart of the Wintergreen Resort. Ski check-in, restaurants, the mountaintop market, & The Mountain Inn are all right across the street! 2-story unit with a main floor primary BR & hall bath. Main floor bonus room with single & trundle. The loft contains 2 twin beds and the 2nd full bath. Parking, pool, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps up to six.

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, 126 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 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, 345 reviews

Five Minute Walk to Everything!

**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, 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 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.

4.99 out of 5 average rating, 148 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 fire pit & patio - 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

An inviting exterior of a two-story home is presented, featuring a blend of wood and stone accents. Large glass windows provide natural light, and snow blankets the ground, creating a serene winter atmosphere. A sloped driveway leads to the entrance, surrounded by trees.

4.85 out of 5 average rating, 127 reviews

Walk to Ski! HotTub PoolTable Shuffleboard Dogs OK

8min walk or 3min drive to ski. Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails. Sleeps 16: K, K, Q, 2 DBL,4 twin, 1PO ★Dogs OK ★2,714sqft ★HOT TUB for 7 ★Sound system ★2-Story vaulted ceiling, gas fireplace, 60"TV ★Dining table for 6 + breakfast bar ★Workspace w/ FAST Wi-Fi ★Shuffleboard ★Pool table Seasonal pool/tennis. Resort access not included. Pet fee $187.

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, 242 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, 214 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.

A spacious outdoor deck features a round dining table surrounded by tall chairs, complemented by a striped couch with soft cushions. An umbrella provides shade, while the scenic mountain views extend into the distance, above a layer of mist.

4.95 out of 5 average rating, 175 reviews

BlueRidge Getaway- Dog Friendly

Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

4.96 out of 5 average rating, 161 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!

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.

4.79 out of 5 average rating, 105 reviews

Your Cozy Mountain Getaway Awaits

This beautifully renovated 2 BR/2 BA mountain condo is centrally located in the Wintergreen Resort - walking distance to the Wintergreen ski resort, tubing park, restaurants and the market! Park your car with no need to move it during your visit. The condo comes fully stocked (including firewood) and is the perfect place for your getaway, including your furry friends (fee).

A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.

4.89 out of 5 average rating, 130 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

Luxury condo furnished with all you need for an exceptional stay. Whether you enjoy the wineries and breweries, hiking the mountain trails, kayaking or paddleboarding, or ski/snowboard, this is the perfect home base for everything Wintergreen has to offer! Just 3/4 of a mile to the resort & slopes and a 50 foot walk from your back door to the shuttle pickup.

Popular amenities for Wintergreen Resort pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.89 out of 5 average rating, 102 reviews

A cozy living room features a classic brick fireplace surrounded by comfortable seating. A colorful area rug adds warmth, while large windows offer views of the greenery outside. Adjacent, a vibrant game room contains a foosball table and warm lighting, ideal for entertainment.

Home in Waynesboro

Gameroom~Gym~Firepit~Main Level BR~Pet OK~Downtown

4.98 out of 5 average rating, 139 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

4.97 out of 5 average rating, 210 reviews

A charming white home features dark shutters and a bright yellow front door, framed by colorful foliage. Flags are displayed at the entrance, and a well-maintained lawn enhances the welcoming appearance. The path and landscaping lead to a warm invitation for guests.

Home in Crozet

Heart of Crozet+ Hotube+Firepit+Wine & Beer+PEACE

4.98 out of 5 average rating, 109 reviews

Home in Roseland

Book for Fall! Nelson 151, MTN views!

A vast expanse of green grass stretches across the foreground, framed by lush orchard trees. Rolling hills covered with foliage rise in the background, under a clear blue sky dotted with soft white clouds, creating a serene rural atmosphere.

4.97 out of 5 average rating, 109 reviews

Perfect getaway among the orchards of Batesville

A spacious, two-story structure with a modern design is surrounded by greenery. The exterior features large, multiple-pane windows framed in red, with a balcony that offers outdoor access. An artistic metal sculpture is positioned in the foreground on a well-manicured lawn.

4.96 out of 5 average rating, 372 reviews

FLASH SALE: Blue Ridge Estate Wine, Beer, & Skiing

A hot tub is positioned on a wooden deck, surrounded by lush greenery and trees. The serene view of the mountains is visible in the distance, complementing the tranquil setting. Steps lead to the hot tub, creating easy access.

4.81 out of 5 average rating, 163 reviews

Misty Mountain Cabin w/spa

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, 171 reviews

Clean family-friendly 5br for wine country getaway

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 41 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 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, 154 reviews

Farmhouse on Working Vineyard

A spacious living area features a comfortable sofa, a wooden coffee table, and a well-lit dining space. Large windows allow natural light to fill the room, and a fireplace adds warmth. Colorful artwork adorns the walls, complementing the light-toned flooring.

4.89 out of 5 average rating, 64 reviews

Wintergreen! Dog friendly, cozy and comfortable

The exterior of a dark-colored mountain home is framed by snow-covered trees, showcasing a pathway lined with bricks leading to the entrance. A spacious deck extends along one side, while a lamp stands on the side, providing soft illumination.

5 out of 5 average rating, 65 reviews

5 min toSki! Valley View DogOK 50"TV Gas Fireplace

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.

4.92 out of 5 average rating, 207 reviews

Wintergreen home, ideal location, dogs welcome!

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.

4.94 out of 5 average rating, 17 reviews

Family and dog friendly with views and pools!

The spacious living room features large windows that frame expansive mountain views. A comfortable sectional sofa and armchairs surround a wooden coffee table. The room is illuminated by natural light, with a stylish chandelier adding elegance. A dining area for six is visible in the background.

4.93 out of 5 average rating, 86 reviews

Designer Home w/ Incredible Views, Sleeps 16

The living area features a spacious gray sectional couch with decorative pillows, a low wooden coffee table, and a patterned area rug. A wood-burning fireplace is situated against a white wall adorned with rustic decor. Natural light enters through large windows.

4.94 out of 5 average rating, 263 reviews

Cozy, clean, quiet mountain condo- King bed

Private, pet-friendly home rentals

The living area features a leather sofa, a glass coffee table, and a wall-mounted TV. Natural light floods through two windows, enhancing the space. A dining table with four chairs is positioned nearby, and a fireplace adds a cozy touch to the room.

4.9 out of 5 average rating, 10 reviews

Walk to Ski! Spacious and Pup Friendly!

A spacious living area is highlighted by a soaring stone fireplace and large windows allowing natural light to filter in. Comfortable seating arrangements are present, complemented by vibrant artwork on the walls. A warm wooden floor adds a cozy touch to the inviting atmosphere.

4.94 out of 5 average rating, 32 reviews

Bluebird Mtn Home ~Dog Friendly ~ ~No step entry~

4.94 out of 5 average rating, 16 reviews

Wintergreen Ski Retreat, Cozy Condo Near Slopes

A balcony view reveals a vast expanse of rolling green mountains under a clear blue sky. A square table is surrounded by two woven chairs, inviting guests to enjoy the serene landscape of the Blue Ridge Mountains and Rockfish Valley.

4.95 out of 5 average rating, 20 reviews

Condo with Valley Views!

A serene mountain landscape is showcased, with a gentle sunrise illuminating the horizon. Lush greenery and rolling hills create depth, while the sun casts a warm glow over the distant mountains, revealing layers of peaks and valleys in soft pastels.

5 out of 5 average rating, 16 reviews

Wow! What A View!

An inviting outdoor space features a hot tub, a gas fire pit, and comfortable seating arrangements. The area is designed for relaxation, showcasing smooth wooden decking and views of the surrounding trees. Sliding glass doors provide access to the interior of the home.

5 out of 5 average rating, 72 reviews

Luxe Modern Retreat: Steps to Ski & Hike! Views!

Guesthouse in Wintergreen Resort

The living area features a comfortable gray sofa positioned near a circular coffee table, complemented by an area rug with a geometric pattern. A moose artwork adorns the wall, while a small dining space and kitchenette with a red refrigerator are visible in the background.

4.94 out of 5 average rating, 48 reviews

Cozy Mountain Retreat * Dog Friendly