
Ski-in/Ski-out vacation rentals in Winhall
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Top-rated ski-in/ski-out rentals in Winhall
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Popular amenities for Winhall ski-in/ski-out rentals
Ski-in/ski-out house rentals

The Mountain Escape
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.

Ski-In/Ski-Out Hike Okemo Mountain Condo
We loved our stay! Just enough snow to still get the ski in/ ski out experience. The home was immaculate, and looked just like the photos. We truly enjoyed our time there and if back at Okemo, will definitely book again!

Hot tub | Shuttle | Ski back home!
Four of us have stayed in 25 Vermont airbnb type places for ski trips in the last 35 years and this is one of the 5 best. The huge living room (comfortable even up to 8), the wood-burning fireplace, and the hot tub are the extra special features of the house. The backyard is very private and peaceful in case you plan to visit in the summer. There is a hawk nest within view of the hottub. Saying the kitchen is stocked with utensils is an understatement. We will return.

Okemo Condo – Ski In/Out
Great location - ski in/out! Close to Jackson Gore base and easy ski lift / drive access to Clock Tower base. Condo was perfect for our family of 4 with 2 kiddos, could accommodate more for sure. Well stocked kitchen. We enjoyed the kids board games! Very comfortable all around and good value for typical cost during winter ski season. Would definitely return!

Summit View Ski and Golf Retreat w/hot tub & Sauna
We came up to celebrate a 40th birthday. Jason’s home was absolutely beautiful and exactly what we were looking for. We had a great time relaxing playing games and soaking in the hot tub. Pictures of Stratton Mountain do not do it justice, it’s so much closer in person and stunning. We loved the fireplace indoors and the outdoor fire pit. We had great weather so we were able to utilize the fire pit and then fireplace at night when it was chilly. Very cozy vibes! We would absolutely recommend this gem and would love to come back! Also, Pearl’s Place Southern Kitchen was delicious, get the bbq!

Modern Chalet: Magic Mountain
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!

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

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Family-friendly, ski-in/ski-out home rentals

Slopeside condo at the base of Okemo-steps to lift
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!

The Sugar House
Nice place, probably better in summer than winter, simply due to more amenities (like screened porch) and better able to appreciate the location, but it was nice as a winter spot, too, to sit and read by the fire. Kitchen was well-equipped, and the place was very clean.

Beautiful 2 Bedrooms in Mountains w/ full kitchen
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.

Sunny Studio Apartment in Hartland
It is a nice place to stay, conveniently located near ski resorts with easy access to the highway. It was perfect for our family of three as a seasonal rental for skiing at Saskadena Six. Nancy was friendly and highly responsive to our requests, making our stay even more enjoyable. Overall, we were very happy with our experience and would highly recommend it!

Slopeside at MT Snow VT
Perfect location to get on and off the mountain. Responsive and helpful. We had a great weekend!

Ski On Ski Off
Great, big condo very close to the Tamarack run/lift. Plenty of space for our family of five. Would definitely stay again!

Walk to Okemo Ski Lift - Private Classic VT Ski Ch
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.

Vermont Getaway Apartment
This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!
Ski-in/ski-out cabin rentals

The Grateful Barn
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!

Beautiful Art Studio with hot tub/sauna #1 Airbnb
Fantastic stay in a fantastic area! We went for a long weekend to celebrate our anniversary and were not disappointed! The cabin was easy to find, cozy, and everything we were looking for. Highly recommend Depot Street Burgers for some good eats in the area!

Stone's Camp on Stamford Stream
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!

The Cozy Little Red Cabin
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!

400+ Airbnb Visits: Incredible Mountain Cabin
Excellent place to stay considering the location and and beautiful views. Owners were excellent, very helpful and did what ever they could to make our experience enjoyable!

The Run-In - Beautiful Country Cabin with Hot Tub
Ben's cabin is nestled in a beautiful location. His cabin is beautifully decorated with unique rustic antiques. The centerpiece of the cabin is the big fireplace that makes the space warm and cozy. There is a hot tub on the patio and a private outdoor shower that must be a delight on a hot summer day. The cabin offers the basic amenities for a comfortable stay. Ben is a responsive host. We would recommend and love to stay again.

Green Mt Getaway: <30m to Bromley Stratton Okemo
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
ﺩ.ﺇ588 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
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Monadnock State Park
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Lake George Expedition Park
- Hooper Golf Course
- Baker Hill Golf Club
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Northern Cross Vineyard
- Pineridge Cross Country Ski Area
- Willard Mountain
- Gooney Golf