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Ski-in/Ski-out vacation rentals in Winhall

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

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Popular amenities for Winhall ski-in/ski-out rentals

Ski-in/ski-out house rentals

Guest favorite
Home in Ludlow
4.92 out of 5 average rating, 13 reviews

Ski-In/Ski-Out Hike Okemo Mountain Condo

StephanieRating, 5 stars3 weeks ago
Words can’t describe the experience we had this weekend. Linda was the best host we have ever worked with and the place was extraordinary to say the least! Extremely clean, comfortable and well located! Kid friendly and close to downtown! We will highly recommend it to friends and family and if we could leave more stars than a 5-star review we would! Looking forward to booking this place again in the near future! Thank you Linda for your amazing hospitality!
Guest favorite
Home in Dover
5 out of 5 average rating, 15 reviews

Private chalet tucked in the green mountains

CarolineRating, 5 stars4 weeks ago
We had a wonderful weekend at Liz’s cabin. Everything was clean. Hot tub was awesome. Would recommend to anyone looking for a beautiful cabin getaway.
Guest favorite
Home in Winhall
4.92 out of 5 average rating, 26 reviews

Multi-Level Ski Retreat at Stratton Mountain

LiliaRating, 5 stars4 months ago
We had a wonderful stay Duojia’s residence! Peaceful location, clean, and the Stratton Mountain view was icing on the cake. There is privacy and so much space at this home. Thank you!
Top guest favorite
Home in Wilmington
5 out of 5 average rating, 30 reviews

Rustic home near skiing & lakes, walk to downtown

KassRating, 5 stars3 weeks ago
Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!
Top guest favorite
Home in Londonderry
5 out of 5 average rating, 12 reviews

Modern Chalet: Magic Mountain

RileyRating, 5 stars2 months ago
Tyler’s place exceeded expectations! The home was exactly as advertised—beautiful, spotless, and in a fantastic location. Check-in and check-out were seamless, making our stay even more enjoyable. Tyler was an outstanding host, incredibly responsive, and went above and beyond by providing detailed information and fantastic restaurant recommendations. I’d highly recommend staying here to anyone looking for a top-notch experience!
Superhost
Home in Dover
4.91 out of 5 average rating, 82 reviews

FULLY renovated 1 bed/1 bath ski in-out condo!

AnastasiaRating, 5 stars2 months ago
My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again
Guest favorite
Home in Wilmington
4.86 out of 5 average rating, 108 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

MarkRating, 5 stars1 month ago
What an amazing experience! Our kids loved every second of it. Our hosts were amazing, responsive, and inviting. The home was beautiful and the scenery was spectacular. I highly recommend staying here. It was a great life experience! Thank you!
Top guest favorite
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars3 months ago
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!

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

Superhost
Condo in Killington
4.92 out of 5 average rating, 106 reviews

Right at Killington !

CrossanRating, 5 stars3 months ago
Our family had a wonderful stay at the condo in Killington. The location could not be beat! A very short 5 minute walk to the lifts and Snowshed lodge. The complex had an amenity building with pool/hot tub that the kids loved and the condo was quite spacious and clean. Ruslana was a great host and very responsive! There is a solid chance we will be back next year!
Superhost
Home in Dummerston
4.96 out of 5 average rating, 130 reviews

The Sugar House

NadiaRating, 5 stars3 months ago
The Sugar House was a fantastic place to stay! It was quiet and peaceful and there was a ton to explore in Burlington VT. The house had a lot of charm. it was cozy, warm, and had everything we needed for the weekend!
Guest favorite
Apartment in Chester
4.89 out of 5 average rating, 501 reviews

Beautiful 2 Bedrooms in Mountains w/ full kitchen

DebRating, 5 stars3 months ago
Nancy is a responsive host who provides clear instructions and offers local recommendations. The apartment we stayed in worked perfectly for our ski weekend at mount snow with 2 teens. Plenty of room and amenities within to foster a fun and relaxed family weekend. The maple syrup for purchase was a delicious touch. Would definitely stay again if we returned to the area.
Guest favorite
Apartment in Ludlow
4.92 out of 5 average rating, 154 reviews

Great Downtown, walk to everything

MikeRating, 5 stars3 months ago
Great space, very conveniently located in town. The host was great, and would definitely stay here again
Guest favorite
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

PatriciaRating, 5 stars2 months ago
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!
Superhost
Condo in Killington
4.8 out of 5 average rating, 107 reviews

Cozy 3BR/2BA Chalet – Mins to Mtn & Biking Trails

MikeRating, 5 stars3 months ago
Dray was thorough and the airbnb was clean, comfortable, and close to everything! I hope to stay here next time I visit!
Top guest favorite
Guesthouse in Hartland
4.95 out of 5 average rating, 992 reviews

Yurt In The Woods - Private Refuge

HeidiRating, 5 stars2 weeks ago
I stayed at Angela’s yurt for Memorial Day weekend. It was exactly as described. My boyfriend and I had a very peaceful long weekend. The space was cozy and adorable and we especially loved the wood burning stove. Was a great stay, would definitely return and highly recommend.
Guest favorite
Chalet in Killington
4.87 out of 5 average rating, 248 reviews

Large Chalet; Sauna, Hot Tub; Walk to Trail

AudreyRating, 5 stars2 months ago
We could not have found a better home for our Killington ski week. The ski in ski out directions were perfect and so easy. The home comfortably accommodated 8 adults and provided privacy for each of us as well. Fabulous dining area for our family that provided many happy memories. We've never rented a home where every single bed was so luxurious either. Each night we slept so soundly. On days we did not ski there was plenty to do at the house, a beautiful neighborhood to walk in and such close proximity to Killington Rd with so many dining options.

Ski-in/ski-out cabin rentals

Superhost
Cabin in Peru
4.79 out of 5 average rating, 92 reviews

The Grateful Barn

ArianeRating, 5 stars3 months ago
We had a wonderful cozy weekend with friends. Leopold’s place was private and tucked away with beautiful snowy Vermont scenery. We went skiing at Okemo (30 min drive) and then relaxed in the cozy living room. The shower was great and the bed was super comfortable. Thank you Leopold!
Superhost
Cabin in Londonderry
4.76 out of 5 average rating, 405 reviews

Beautiful Art Studio with hot tub/sauna #1 Airbnb

Bari Rating, 5 stars2 days ago
We had a wonderful time in this beautiful rural Vermont oasis. Exactly what we were looking for! The place is quintessential VT…. So if you are looking to spend a few nights in a reconverted barn on farmland…. Well, this is it. We loved being able to walk the property, and the jacuzzi and sauna were a real highlight. Directions getting in and figuring out our building were a bit confusing at first but we figured it out. We had a few small issues but Ben was responsive and did his best to take care of them quickly - with varying levels of success. The outdoor area could use some easier access and a bit more attention, but we were told that it is in the works. We would stay again in a heartbeat!
Guest favorite
Cabin in Woodford
4.98 out of 5 average rating, 145 reviews

Stone's Camp on Stamford Stream

ThomasRating, 5 stars8 months ago
This was our second stay at Stone's Camp. It was just as great as the first stay. It's very private, peaceful and relaxing. We enjoyed hiking around the area and never had to leave the property in our car during our 4 night stay. The walk from the camp down the abandoned road to the washout is perfect. Our dogs enjoyed being off leash and exploring the woods and stream. It was especially nice for our 15 yro dog who is now unable to tackle larger hikes. Nights were spent enjoying a campfire by the babbling stream on rain free nights. Rainy nights were spent playing cards and games around the table indoors. If you are looking for something quiet, private and love to be outside and away from it all this is the place for you. If you have dogs it's the place for them as well. Thank you again, Chuck, for sharing your piece of paradise and thanks for accommodating our daughter and her boyfriend at the last minute who surprised us with a visit from the West Coast. We hope to be back!
Superhost
Cabin in Cavendish
4.95 out of 5 average rating, 159 reviews

The Cozy Little Red Cabin

LaurenRating, 5 stars3 months ago
Marinas little red cabin was perfect for our ski trip! The WiFi is a little rough but we didn’t spend much time on our phones Bring dvd’s (the collection is solid but more the better) Perfect distance to okemo, Stowe is less than two hours so it was great! The cabin felt so cozy and felt right at home! Would def book again!
Superhost
Cabin in Rutland
4.82 out of 5 average rating, 28 reviews

Blue Cozy Ski House

LindsayRating, 5 stars3 weeks ago
It was a great place to stay and very convenient and easy. Thank you!
Superhost
Cabin in Londonderry
4.67 out of 5 average rating, 434 reviews

The Run-In - Beautiful Country Cabin with Hot Tub

KevinRating, 5 stars1 week ago
One of my favorite Airbnb I’ve stayed so far. It was a perfect getaway, but also drivable distance from groceries stores. The amenities were amazing and the host Ben especially was super friendly, and their dog and their family as well. will definitely come back.
Guest favorite
Cabin in Londonderry
4.88 out of 5 average rating, 74 reviews

Green Mt Getaway: <30m to Bromley Stratton Okemo

JessicaRating, 5 stars3 months ago
Cliff is very easy to communicate with. The house is in a great location, easy to find, and close to several ski resorts, making it very convenient for skiing. The room is comfortable and warm, and the kitchen is well-equipped, allowing you to cook your own meals. The game room, in particular, is a paradise for children, with countless games for you to enjoy. This was a wonderful experience, and I will definitely come back in the future.

Quick stats about vacation rentals that are ski-in ski-out in Winhall

  • Total rentals

    30 properties

  • Nightly prices starting at

    R2,873 ZAR before taxes and fees

  • Total number of reviews

    730 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore