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, 144 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 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, 196 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

Apartment 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, 108 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!

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

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, 114 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.

4.95 out of 5 average rating, 333 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.

A cozy living room features comfortable seating on a sofa and armchair, complemented by a round coffee table. A smart TV is positioned above a fireplace with subtle artwork on the wall. Natural light filters through large windows, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 101 reviews

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

Step into the allure of our fantastic Wintergreen, just a leisurely 4min stroll away from the heart of Wintergreen's mtn action! Tucked away in a serene and tranquil nook of the mountain, our meticulously curated property combines serene relaxation with unfettered access to the thrilling outdoor adventures that await nearby. The closest hiking trail is within 200 yds! Whether you're a couple seeking a romantic retreat or a small, fun family, our home is eager to embrace your mountain dreams!

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.

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, 259 reviews

Cozy, clean, quiet mountain condo- King bed

Everything you need to make your getaway relaxing and convenient has been thought out in this tastefully decorated condo including new King Bed, Queen sofa pullout bed, plush linens, new spacious couch, 55" Smart TV, Roku, 1 Gbps internet, WiFi, DVD player & movies, fully equipped kitchen, dining area for 4, wood burning fireplace, and private patio. Non-smoking condo. Please provide all guest names and dog info if applicable upon inquiry or booking. No cats or other animals accepted.

4.98 out of 5 average rating, 209 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, 165 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!

4.97 out of 5 average rating, 148 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!

Popular amenities for Wintergreen Resort pet-friendly home rentals

Kitchen

Wi-Fi

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, 39 reviews

4.97 out of 5 average rating, 142 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, 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

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, 68 reviews

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

4.95 out of 5 average rating, 263 reviews

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.

Home in Afton

CritzerHouse - on 151- Walk to the Brewery!

4.98 out of 5 average rating, 105 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, 104 reviews

Cozy, relaxing mountain getaway on the golf course

4.96 out of 5 average rating, 366 reviews

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.

Home in Afton

A Funky Blue Ridge Estate for Wine & Beer Lovers

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

Apartment in Wintergreen Resort

An outdoor dining setup on a spacious deck features several plates with a breakfast spread, including eggs, fruit, and pastries. A steaming cup and a glass of juice are present. In the background, a telescope is positioned to enjoy the scenic mountain view under a cloudy sky.

4.97 out of 5 average rating, 39 reviews

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

4.93 out of 5 average rating, 153 reviews

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.

Home in Afton

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.

4.91 out of 5 average rating, 58 reviews

Wintergreen! Dog friendly, cozy and comfortable

Apartment 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, 12 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, 133 reviews

The Bear Dance Cabin at Wintergreen Resort

4.93 out of 5 average rating, 75 reviews

Mountain View Aspen Suite – Two Fireplaces

A view from the back deck showcases a snowy landscape with scattered trees. The blue sky provides a bright backdrop, and snow covers the ground, reflecting the sunlight. An Adirondack chair sits in the foreground, inviting guests to relax while enjoying the scenic surroundings.

4.96 out of 5 average rating, 82 reviews

Ski In/Out! Slope Side - Eagles Swoop!

Private, pet-friendly home rentals

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.

4.93 out of 5 average rating, 29 reviews

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

4.94 out of 5 average rating, 36 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!

5 out of 5 average rating, 15 reviews

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

The exterior of a wooden Treeloft home is surrounded by lush greenery, with a gently sloping pathway leading to the front door. The structure features a shaded porch area and large windows that invite natural light while blending with the natural landscape.

4.94 out of 5 average rating, 17 reviews

The Distinguished Squirrel Chalet walking distance

A patio area features a round table surrounded by four metal chairs, offering a clear view of the expansive landscape. The sky displays vibrant hues of orange and pink as the sun sets over the distant mountains, creating a serene backdrop.

4.98 out of 5 average rating, 42 reviews

Breathtaking Views from The Ledges

Superhost

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.

Guesthouse in Wintergreen Resort

4.93 out of 5 average rating, 45 reviews

Cozy Mountain Retreat * Dog Friendly

A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.

4.97 out of 5 average rating, 29 reviews

Recently updated - views of the Blue Ridge Mtns