Ski-in/Ski-out vacation rentals in Wintergreen Resort

Find and book unique ski-in/ski-out homes on Airbnb

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Popular amenities for Wintergreen Resort ski-in/ski-out rentals

Ski-in/ski-out house rentals

Top guest favorite
A cozy living area features a stone fireplace with a wooden mantel, displaying potted plants and candles. A modern gray sectional sofa is positioned nearby, complemented by a rustic rocking chair adorned with a colorful cushion. The warm tones of the wooden ceiling create an inviting ambiance.
Home in Wintergreen Resort
5 out of 5 average rating, 17 reviews

Wintergreen condo ski-in/ski-out

DaranRating, 5 stars1 month ago
It was a beautiful place that felt like home. The owners were amazing and responded very quickly. We will definitely come back!
Top guest favorite
A cozy living area is centered around a rustic fireplace, enhanced by warm wood accents. Stockings hang from the mantle, while a plush sectional sofa offers ample seating. Natural light streams in through large windows, highlighting the tranquil atmosphere of the space.
Home in Wintergreen Resort
5 out of 5 average rating, 18 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

RichardRating, 5 stars1 month ago
Could not be happier with this location. The photos don’t do it justice. Everything was just as described. The host proactively reached out, made herself available if we needed anything, and even created a little guide for recommendations. The whole place was spotless, so well maintained, and pride in ownership really showed. They even had coffee pods for coffee maker waiting in the kitchen. It was beautiful, peaceful, and safe. Thank you again.
Guest favorite
The living room features high ceilings with exposed beams and large windows showcasing the surrounding trees. A light gray sofa and armchairs provide comfortable seating, while a round coffee table sits at the center. A jute area rug adds texture to the hardwood floor.
Home in Wintergreen Resort
4.94 out of 5 average rating, 50 reviews

Treeloft 17: Ski in/ski out – EV charger – 3BR/3BA

JulieRating, 5 stars1 month ago
We stayed here when our oldest graduated from law school. It was a great place for our family to celebrate her accomplishment together. The place was beautiful and our evening walk was one of our favorite memories. The only downside was our elderly mother (83 years old) had some issues getting up the stairs to the house. So if you have mobility challenged people in your family, you will need to be prepared to help them.
Top guest favorite
The exterior of a modern mountain condo is showcased, featuring a wooden ramp leading to the entrance. The structure is framed by trees and includes triangular windows that complement the wood siding, creating a harmonious blend with the natural surroundings.
Home in Wintergreen Resort
4.93 out of 5 average rating, 59 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

KristenRating, 5 stars3 months ago
Great location next to slopes and restaurants! Easy to get to, park out front and easy access to enter. Cozy and comfortable inside and everything available we would need for the weekend. Appreciated the plentiful firewood right out front. We enjoyed our stay and hope to be back in the summer! Thank you for sharing your mountain condo with our family!
Superhost
A Great Room is presented, featuring two dark leather sofas and a wooden coffee table at its center. Large windows offer views of the surrounding trees, while a mounted television and a lamp complete the space. A vibrant area rug adds color to the wooden floor.
Home in Wintergreen Resort
4.7 out of 5 average rating, 63 reviews

Cliff Hanger Hot Tub Dogs OK Pool Tennis Golf Hike

AameirRating, 5 stars3 days ago
It was a wonderful experience living in this beautiful listing. The host was extremely nice and friendly and helped us to get a wonderful experience in this beautiful resort.
Superhost
A living room area features a queen sofa bed, accented with decorative cushions. A small green side table is positioned beside a cozy armchair. A colorful area rug lays on the floor, and wall art depicting a serene forest scene adds visual interest. Natural light enters from a nearby window.
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Casa Perfecta

JosephRating, 5 stars2 weeks ago
We had an amazing stay at this beautiful condo in the mountains! The location is perfect for anyone looking to hit the slopes or tour the grounds – making it great destination year round. The condo itself is cozy, clean, and has everything you need for a comfortable stay. The kitchen was well-equipped, which made it easy to cook meals before heading out for the day. The beds were super comfortable, and we slept like babies every night! The host was incredibly helpful, providing us with all the information we needed for the resort, and even sent us local recommendations for dining and things to do in the area. Check-in and check-out were a breeze. Would definitely recommend this place to anyone looking for a relaxing, convenient, and picturesque retreat. We’ll be back next year for sure!
Superhost
A spacious living area is highlighted by high vaulted ceilings and a cozy wood-burning fireplace. Large glass doors invite natural light, opening to a view of the greenery outside. A spiral staircase leads to an upper loft, offering additional living space. Two lamps provide soft illumination.
Home in Wintergreen Resort
4.81 out of 5 average rating, 47 reviews

Cozy cabin/WalktoResort&Hiking/PupFriendly

AmyRating, 5 stars2 weeks ago
We had a lovely stay at The Good Life! The home was easy to find, clean, and walkable to areas with beautiful views. We were blessed with good weather and the deck was a wonderful place to enjoy it. The kitchen was well-stocked and included coffee beans and a grinder for a delicious cup of coffee each morning. Upon our arrival, we were greeted with a bottle of wine and bottles of water in the refrigerator. The host was responsive to any questions I had prior to arrival. We would not hesitate to stay at The Good Life again!
Top guest favorite
A spacious dining area features a rustic wooden table, seats for eight, and a light blue runner. Large windows allow natural light to fill the space, providing views of the surrounding greenery. The open layout connects to the kitchen, enhancing the airy atmosphere.
Home in Wintergreen Resort
5 out of 5 average rating, 59 reviews

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

ChristineRating, 5 stars1 month ago
The house was awesome! Clean, comfortable, parking, beautifully decorated. Bed rooms, kitchen and bathrooms were amazing and stocked well. The views were amazing! Loved the covered seating area outside. Beautiful. Highly recommend the house!

Family-friendly, ski-in/ski-out home rentals

Guest favorite
A deck is shown with black wrought iron furniture, including a small table and chairs. Fallen leaves are scattered on the wooden surface. Surrounding trees display autumn foliage, revealing distant mountain views under a cloudy sky.
Cabin in Wintergreen Resort
4.92 out of 5 average rating, 37 reviews

Eagle's Lookout Retreat at Wintergreen Resort, VA

QuincyRating, 5 stars5 months ago
Family friendly location with outstanding views. Very close to slopes.
A cozy living area features large windows that provide scenic views of the surrounding landscape. Two comfortable sofas in dark leather are positioned around a wooden coffee table, while soft lamps illuminate the space. A patterned rug enhances the ambiance.
Home in Roseland
4.7 out of 5 average rating, 37 reviews

Tyro Slope Side Home Ski In/Out w/ Yr Round Views

KateRating, 5 stars27 months ago
We had a great stay! House is in a wonderful location and Eric provided timely check-in information. We love this area and will definitely be back!
A view from a covered deck captures the snowy landscape outside, featuring gently sloping hills, trees, and distant mountains. A colorful sled lies on the snow, while an American flag flutters nearby. The scene conveys a serene winter atmosphere.
Condo in Wintergreen Resort
4.78 out of 5 average rating, 18 reviews

Slope Side 2 Bed Condo. Location Location Location

CayleeRating, 5 stars5 months ago
We had the best stay! So incredible! SO CLOSE to the slopes (practically ski in/ski out) within steps to the main green slopes and can see one of the blue slopes right outside! We will be back! So thankful and had so much fun! Also had ski locker/closet right outside room so really easy with my 9 year old!
Top guest favorite
A cozy room features a bed with a light quilt, decorative pillows, and a patterned throw. Nearby, a small TV is placed on a dresser painted in a soft color. Wall decorations include shelves with teal ornaments and woven baskets, complementing a small potted plant.
Private room in Nellysford
4.95 out of 5 average rating, 334 reviews

The Wintergreen Ranch

DarrenRating, 5 stars3 days ago
My wife and I went to Nellysford as part of her birthday month. We booked Kelly's place because of the closeness to many attractions and the views. We didn't realize how beautiful it was until we arrived; surrounded with mountain views and a pond out front. Even saw an old plane take off and land as their property backs up to a small grass air strip! Great host with a beautiful home! We opted for the chef prepared breakfast, which was delightful! Great coffee, too. We can't wait stay here again!
The multi-story building is nestled among trees, featuring a set of wooden stairs leading to the entrance. Large windows are visible on each floor, allowing natural light to penetrate. A directory sign with multiple unit numbers is displayed at the base of the steps.
Apartment in Roseland
4.82 out of 5 average rating, 235 reviews

Spacious 2 bedroom, 2 bath condo w/ full kitchen

SusanRating, 5 stars6 months ago
Great stay. Not updated, but extremely comfortable. Bed was great! We really enjoyed the fireplace. Everything we needed for a short stay. Small suggestion… get rid of the cable and tv and buy a smart tv for streaming. Thanks for a great stay and for allowing us a later checkout. Much appreciated.
Superhost
The three-level home is set amidst tall trees, showcasing large windows that illuminate the exterior at night. A multi-level deck is visible, offering views of the surrounding snow-covered landscape. The design emphasizes a seamless connection with nature, framed by natural foliage.
Home in Wintergreen Resort
4.88 out of 5 average rating, 60 reviews

Slopes @ Tyro

MeganRating, 5 stars16 months ago
Perfect house for our family ski trip! Plenty of space and great location for skiing. Will definitely be staying here again!
Guest favorite
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.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 37 reviews

Breathtaking Views from The Ledges

LoganRating, 5 stars4 months ago
house was very well stocked for an Airbnb (games, kitchen stuff, household items, etc), having an onsite firewood supply was amazing as was being within walking distance of some of the slopes. Vivian's instructions were very clear on the check in/check out procedure and everything was described accurately. Would stay here again!

Ski-in/ski-out cabin rentals

Top guest favorite
A charming cabin is nestled among trees, with a spacious deck visible from the exterior. Bright yellow daffodils bloom in the foreground, contrasting with the earthy tones of fallen leaves. The tranquil setting conveys a serene connection to nature.
Cabin in Wintergreen Resort
5 out of 5 average rating, 45 reviews

Summer Getaway at Oak Ledge! Trails+Tastings+Peace

KenRating, 5 stars3 weeks ago
Tyler & Meredith were wonderful hosts. They were proactive, friendly and a wealth of knowledge regarding local recommendations. Their home was a place of serenity in a beautiful mountain location. We look forward to the next time we travel to Wintergreen and can take advantage of Tyler & Meredith’s warm hospitality.
Superhost
The exterior of a mid-century modern home is surrounded by lush greenery. A spacious deck wraps around the side, featuring a mix of railings and a balcony. The building is designed with asymmetrical angles and large windows, inviting natural light into the interior.
Cabin in Wintergreen Resort
4.86 out of 5 average rating, 37 reviews

Bide-a-Wee- Hike the Trails! Close to the slopes!

KatieRating, 5 stars4 months ago
We had a great stay! This place had everything we needed in a great location.
Cabin in Wintergreen Resort
4.45 out of 5 average rating, 66 reviews

Smoky Bear Cabin

Brian And TraceyRating, 5 stars1 month ago
Abby is a great host, always responsive and the house was perfect for our stay with lots of space for everyone to spread out. I loved sitting on the back porch it is such a peaceful location!
A two-story cabin is nestled among trees, showcasing a sloped roof with multiple gables. A wooden walkway leads to the entrance, flanked by greenery. Large windows allow for natural light, contributing to a warm, inviting appearance.
Cabin in Wintergreen Resort
4.73 out of 5 average rating, 70 reviews

Slope Side Suite

NancyRating, 5 stars3 months ago
Great place, short walk to slopes. Close to the market that is stocked with food and has great deli, breakfast muffins and bakery items.
Cabin in Wintergreen Resort
4.59 out of 5 average rating, 34 reviews

Cozy 'Hillside Hideaway' in Wintergreen Resort!

SaraRating, 5 stars4 months ago
We had a great time! A very clean and beautiful place, very convenient and close to the lodge area. Only downside was we had a bit of a hard time keeping the downstairs rooms warm.
The exterior of the home is set against a backdrop of bare trees, showcasing a green and beige structure with a sloped roof. A gravel pathway leads to the house, with a fenced area visible at the front and a deck extending from the entrance.
Cabin in Wintergreen Resort
4.86 out of 5 average rating, 35 reviews

A warm mountain top home, steps from the slopes.

JulieRating, 5 stars7 months ago
Steph's cabin was the perfect, serene retreat I needed. Everything was clean and comfortable, and Steph's instructions were so thorough I only needed to contact her once - and she responded immediately. The neighborhood is gorgeous and peaceful, I'll be back in the winter to enjoy some snow!
Superhost
The A-frame cabin is nestled among lush greenery, featuring a wooden deck with a staircase leading to the entrance. Large glass windows emphasize the structure's height, allowing natural light to illuminate the interior. A gravel driveway provides access, surrounded by dense forest.
Cabin in Wintergreen Resort
4.87 out of 5 average rating, 30 reviews

COZY A-Frame Spacious Deck w/ Grill

AngelinaRating, 5 stars1 month ago
It was a cozy place to stay in celebration of my graduation. Hosts were responsive and quick with any inquires. There was extra soap for those that needed it and everything was easy to find in the house. The house served the purpose of bringing everyone together for this grand occasion! Thank you :-)
The exterior of a two-story wooden accommodation is shown, surrounded by snow-covered trees. Large glass windows reflect natural light, while a broad deck offers space for outdoor relaxation. Balcony areas can be seen on the upper level, enhancing the structure's connection to the tranquil surroundings.
Cabin in Wintergreen Resort
New place to stay

The Eagle Ranch

Quick stats about vacation rentals that are ski-in ski-out in Wintergreen Resort

  • Total rentals

    110 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Destinations to explore