Ski-in/Ski-out holiday rentals in Madison

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

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

Family-friendly, ski-in/ski-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 stars19 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, 276 reviews

Orchard Prairie B&B

DavidRating, 5 stars2 weeks ago
Wow the place is much bigger than the photos show!!!! We saw maybe two or three bugs over the three nights we were there — which is to be expected when the place is next to the woods. The area is absolutely gorgeous. And do check out the Ski-Hi Farm that they own up the hill!
Guest favourite
Guesthouse in Stoughton
4.94 out of 5 average rating, 374 reviews

Country cabin, birders paradise.

PaulRating, 5 stars2 weeks ago
If you like a peaceful country setting with beautiful walking areas (among occasional passing goats too!) and a cozy woods cabin, this is the place for you. Only minutes from downtown Stoughton, warm generous hosts, and friendly neighbors.
Guest favourite
Guest suite in Midvale Heights
4.91 out of 5 average rating, 172 reviews

Hospitality+Kitchen+Laundry+Gardens

BrettRating, 5 stars1 month ago
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, 214 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

BenjaminRating, 5 stars1 week ago
We had a wonderful, relaxinf weekend ar Jeff and Emily’s Cabin. The cabin itself is cozy and clean. There are huge windows to allow you to look out at the beautiful nature surrounding their farm. We really enjoyed using the firepit and relaxing on the grounds - it is far from a major road and felt very private. The hosts were responsive and introducd themselves, but also made sure to give us privacy and space to relax. I hope we can come back and visit soon!
Private room in Albion
4.47 out of 5 average rating, 72 reviews

Beachkonong gr8 sunrise n shine

JesseRating, 5 stars1 month ago
Michael was a ton of fun and his house is excellent for a bachelor party!
Cabin in Wisconsin Dells
4.73 out of 5 average rating, 89 reviews

Christmas Mountain 2br Golf 27 holes Pools Ski too

DianaRating, 5 stars10 months ago
We loved loved our stay. Will definitely come back.

Ski-in/ski-out condo rentals

Guest favourite
Condo in Wisconsin Dells
4.91 out of 5 average rating, 96 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

DusanRating, 5 stars5 months ago
Amazing place .highly recommend!!
Superhost
Condo in Wisconsin Dells
4.77 out of 5 average rating, 75 reviews

Luxurious Chula Vista Retreat

WendyRating, 5 stars1 week ago
The host Matt was very responsive and easy to communicate with. The place was nice, dated, but nice and very spacious. The listing was very clear about not coming with water Park passes, so no surprises, but the passes are very expensive for what you get for them. Other big water parks in the area are much better and cheaper. That is the resort itself, not a host thing. other things about the resort is the pools have limited hours and they aren't always open. Again, not a unit thing, just a heads up about the resort. For kiddos that like arcades, it's pretty decent. The breakfast buffet was great, but we didn't eat any other meals at the resort. The beds were comfortable and had really nice soft blankets. There is absolutely zero counter space in the master bath, but that's in the pictures, so again no surprise. Overall great stay, great unit, awesome host communication. The resort was just ok.
Superhost
Condo in Wisconsin Dells
4.8 out of 5 average rating, 40 reviews

Dells Paradise - Families & Beach Lovers

RedRating, 5 stars3 weeks ago
We had such a great time during our stay in Wisconsin Dells! The accommodations were absolutely wonderful—clean, comfortable, and perfectly located. The condo was spacious and well-kept, with all the amenities we needed to feel right at home. It was clear that the staff takes pride in maintaining a welcoming and relaxing environment. One of the best parts of our trip was how many coupons and discounts were available to us. We made sure to take full advantage of them! From local attractions to dining and entertainment, we saved quite a bit just by using the deals that were provided. It really made the whole experience feel like an even better value. Overall, we couldn’t have asked for a better place to stay or a better way to experience everything the Dells has to offer. Highly recommend for anyone looking to have a fun, affordable, and comfortable getaway!
Superhost
Condo in Wisconsin Dells

Dells Family Stacation-Lake Access-Hiking-Golf

IgorRating, 5 stars3 weeks ago
Enjoyed our time at the house

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