
Ski-in/Ski-out vacation rentals in Wintergreen Resort
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Top-rated ski-in/ski-out rentals in Wintergreen Resort
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
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Popular amenities for Wintergreen Resort ski-in/ski-out rentals
Ski-in/ski-out house rentals

Wintergreen condo ski-in/ski-out
It was a beautiful place that felt like home. The owners were amazing and responded very quickly. We will definitely come back!

Premiere 2 BR Getaway Ski In/Out Wintergreen Condo
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.

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

Wintergreen Condo~ 1 Minute To Four Seasons Resort
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!

Cliff Hanger Hot Tub Dogs OK Pool Tennis Golf Hike
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.

Casa Perfecta
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!

Cozy cabin/WalktoResort&Hiking/PupFriendly
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!

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

Eagle's Lookout Retreat at Wintergreen Resort, VA
Family friendly location with outstanding views. Very close to slopes.

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

Slope Side 2 Bed Condo. Location Location Location
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!

The Wintergreen Ranch
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!

Spacious 2 bedroom, 2 bath condo w/ full kitchen
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.

Slopes @ Tyro
Perfect house for our family ski trip! Plenty of space and great location for skiing. Will definitely be staying here again!

Breathtaking Views from The Ledges
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

Summer Getaway at Oak Ledge! Trails+Tastings+Peace
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.

Bide-a-Wee- Hike the Trails! Close to the slopes!
We had a great stay! This place had everything we needed in a great location.

Smoky Bear Cabin
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!

Slope Side Suite
Great place, short walk to slopes. Close to the market that is stocked with food and has great deli, breakfast muffins and bakery items.

Cozy 'Hillside Hideaway' in Wintergreen Resort!
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.

A warm mountain top home, steps from the slopes.
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!

COZY A-Frame Spacious Deck w/ Grill
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 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
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