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Ski-in/Ski-out holiday rentals in Winhall

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

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Popular amenities for Winhall ski-in/out rentals

Ski-in/out house rentals

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

Ski-In/Ski-Out Hike Okemo Mountain Condo

StephanieRating, 5 stars2 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 favourite
Home in Dover
5 out of 5 average rating, 14 reviews

Private chalet tucked in the green mountains

Zach & CourtneyRating, 5 stars2 months ago
Liz's place was the great! Beautiful, clean, and conveniently located to the mountain. Everything we needed for a long ski weekend with friends! Thank you!
Superhost
Home in Jamaica
4.93 out of 5 average rating, 15 reviews

The Mountain Escape

DanRating, 5 stars3 months ago
Great space! We were comfortable with a big group here, and loved being so close to the slopes. Hot tub seems new and is in great condition.
Guest favourite
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 favourite
Home in Wilmington
5 out of 5 average rating, 30 reviews

Rustic home near skiing & lakes, walk to downtown

KassRating, 5 stars2 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 favourite
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 favourite
Home in Wilmington
4.86 out of 5 average rating, 108 reviews

MtSnow* HotTub* Pool * AirHockey*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!

Family-friendly, ski-in/out home rentals

Guest favourite
Apartment in Ludlow
4.95 out of 5 average rating, 116 reviews

Slopeside condo at the base of Okemo-steps to lift

GladisRating, 5 stars3 months ago
Loved Kristin’s place, the best part was that it was right on the mountain. Perfect for a family of 4, will definitely comeback. Beds were comfortable and the living room was very cozy. Loved the mural. Thank you Kristin!
Guest favourite
Flat 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 favourite
Flat 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 favourite
Apartment in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 month ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favourite
Home in Ludlow
4.91 out of 5 average rating, 98 reviews

Walk to Okemo Ski Lift - Private Classic VT Ski Ch

MeredithRating, 5 stars3 months ago
Our family really enjoyed our stay at the trailside chalet! A quick walk up the road to the ski lifts and plenty to keep us entertained after a day of skiing. We really enjoyed the fire place and pool table!! Prescott was a great host, quick to respond to our questions.
Apartment in Dover
4.59 out of 5 average rating, 34 reviews

Summer Living On Hillside Condo on Mount Snow

RyanRating, 5 stars10 months ago
We had a nice getaway at Paul's place. The place fit our needs perfectly. We enjoyed the use of both the indoor and outdoor pool. You do need to reserve times online for use of the pools or other activities but we never had any issue with that. There are several great restaurants nearby and we enjoyed walking the nearby trails and shopping in Wilmington and Dover.
Home in Landgrove
5 out of 5 average rating, 24 reviews

Landgrove Charm - Post and Beam Barn House

ChristopherRating, 5 stars2 weeks ago
Instantly honey. So many places are sterile. This home truly feels lived in. And, at once, you can feel at home. Well equipped for all of our needs (four adults, three children). Special mention to Matt, the caretaker, for being super responsive and on top of things. Wake up early to watch the bobolinks, or get comfortable on the porch in the afternoon to watch the hawks hunt. A perfect stay in every way
Guest favourite
Apartment in Stratton
4.92 out of 5 average rating, 62 reviews

Ski On/Off Condo in the Heart of Stratton Village!

MarkRating, 5 stars3 months ago
Not only is this place perfectly located, but it also says everything you need. The decor is a little out of date, but very comfortable (the beds were surprisingly comfortable!). The entryway was perfect to keep our ski stuff organized, and the garage and driveway. We’re really appreciated. I wouldn’t hesitate to rent this place again.

Ski-in/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 starstoday
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 favourite
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 Londonderry
4.67 out of 5 average rating, 434 reviews

The Run-In - Beautiful Country Cabin with Hot Tub

KevinRating, 5 stars6 days 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 favourite
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 holiday rentals that are ski-in/out in Winhall

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹13,774 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