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Ski-in/Ski-out holiday rentals in Wintergreen

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

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Popular amenities for Wintergreen ski-in/out rentals

Ski-in/out house rentals

Top guest favourite
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 favourite
Home in Wintergreen Resort
5 out of 5 average rating, 19 reviews

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo

TimRating, 5 stars2 days ago
this private condo at wintergreen was perfect for my family and I, with a 15 month old it was very baby friendly and the view took our breath away. the host was very responsive and checked in before during and after the stay to make sure we had everything we r needed. I would 100% recommend this for your next getaway.
Guest favourite
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 favourite
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
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Perfect house

JosephRating, 5 stars3 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
Home in Wintergreen Resort
4.81 out of 5 average rating, 47 reviews

Cozy cabin/WalktoResort&Hiking/PupFriendly

AmyRating, 5 stars3 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 favourite
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!
Top guest favourite
Home in Wintergreen Resort
5 out of 5 average rating, 20 reviews

New Wintergreen Walk Slopes/Hot-tub/ Sauna/Pets OK

MollyRating, 5 stars2 months ago
Wonderfully cozy home for our peaceful and outdoorsy spring break getaway. The home was perfect for our family of four. The bedrooms are bright and cheery with comfy beds and linens. Great kitchen and kids really enjoyed the game room. Joshua was a great host, providing timely, clear instructions and a helpful electronic guidebook for enjoying the area. He was also very responsive and kind enough to provide us with a flexible check-in/out time since our stay was in the off season. Highly recommend the Snowflake Inn and look forward to a return stay.

Family-friendly, ski-in/out home rentals

Guest favourite
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.
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 stars28 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!
Apartment 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 favourite
Private room in Nellysford
4.95 out of 5 average rating, 334 reviews

The Wintergreen Ranch

DarrenRating, 5 stars1 week 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!
Flat 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
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 favourite
Apartment 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/out cabin rentals

Top guest favourite
Cabin in Wintergreen Resort
5 out of 5 average rating, 45 reviews

Summer Getaway at Oak Ledge! Trails+Tastings+Peace

KenRating, 5 stars4 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
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!
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.
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
Cabin in Wintergreen Resort
4.87 out of 5 average rating, 31 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 :-)
Cabin in Wintergreen Resort
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The Eagle Ranch

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