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

Ski-In/Ski-Out Hike Okemo Mountain Condo
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!

Private chalet tucked in the green mountains
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!

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.

Multi-Level Ski Retreat at Stratton Mountain
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!

Rustic home near skiing & lakes, walk to downtown
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!

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
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

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!

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.

Great Downtown, walk to everything
Great space, very conveniently located in town. The host was great, and would definitely stay here again

Mt Snow Ski In/Out at Seasons
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.

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.

Summer Living On Hillside Condo on Mount Snow
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.

Landgrove Charm - Post and Beam Barn House
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

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

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
The cabin was beautiful and perfect for a getaway from the city! We loved watching the sunset from the hot tub and cooking in the beautiful kitchen.

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 Run-In - Beautiful Country Cabin with Hot Tub
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.

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 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
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Six Flags Great Escape Lodge & Indoor Water park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Lake George Expedition Park
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area