Ski-in/out vacation rentals in Madison

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

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Popular amenities for Madison ski-in/out rentals

Family-friendly, ski-in/out home rentals

Guest suite in Edgerton
4.71 out of 5 average rating, 95 reviews

End of the road Lake House/ Super Quiet.

QianRating, 5 stars17 months ago
Mike and his wife are really nice people. They tried their best to help with everything!
Superhost
Apartment in Baraboo
4.87 out of 5 average rating, 272 reviews

Orchard Prairie B&B

TomRating, 5 stars7 months ago
Our second stay there. Great value, and location just west of Devils Lake State Park. With a 5 minute walk each morning up the hill to a wonderful orchard farm market/bakery for fresh made apple cider donuts and coffee.
Top guest favourite
Guesthouse in Stoughton
4.94 out of 5 average rating, 367 reviews

Country cabin, birders paradise.

SaraRating, 5 stars1 week ago
What a relaxing stay! Gwen and Ed are just a delight! Our dogs absolutely loved the whole cabin and yard. Our older dog thought the rug in the little bedroom was his personal bed :) The bed was comfortable and the bathroom might be small but it still had enough room. We saw lots of birds and enjoyed the Badfish Creek area. This place is definitely on our must return list!
Top guest favourite
Guest suite in Madison
4.91 out of 5 average rating, 172 reviews

Hospitality+Kitchen+Laundry+Gardens

BrettRating, 5 starstoday
I stayed here during a work conference. The space is private, though connected to the main residence. The space is the basement of the home. There is a full bath and full kitchen, and a very comfortable king bed. It was very quiet and peaceful. The host was very friendly and communicative and helpful. The residence is close to a grocery store and several restaurants and close access to Beltline Highway. I would stay again!
Guest favourite
Farm stay in Plain
4.94 out of 5 average rating, 208 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

LisaRating, 5 stars6 days ago
Jeff and Emily’s cabin provided a perfect homebase for exploring the outstanding local food and art scene of the Driftless region. We found the vintage cabin exactly as described…it was spotless, warm, bright. We especially loved the handmade quilts, cozy bed, comfy pillows, lush linens, and the lovely handmade ceramic dishes made by the local artisans at Wilson Creek Pottery. The view is indeed fantastic! Sitting by the firepit at sunset (with occasional visits from the friendly barn cats and chickens) was a highlight. Emily was quick to respond, warm and friendly, and provided great recommendations. We are looking forward to our next (and hopefully longer!) visit. Lisa and Rich
Private room in Albion
4.46 out of 5 average rating, 70 reviews

Beachkonong gr8 sunrise n shine

ChrisRating, 5 stars21 months ago
Michael was very kind and easy to communicate with.
Cabin in Wisconsin Dells
4.73 out of 5 average rating, 89 reviews

Christmas Mountain Village Onsite SKI Tubing GOLF

DianaRating, 5 stars8 months ago
We loved loved our stay. Will definitely come back.

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