Ski-in/Ski-out vacation 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

Ski-in/ski-out house rentals

Guest favorite
The living room features laminate hardwood floors and bright windows that allow natural light to fill the space. A gray sofa is positioned next to a coffee table, with a cozy chair nearby. A round mirror and artwork add personal touches to the minimalist decor.
Home in McFarland
4.84 out of 5 average rating, 130 reviews

The little Green Birdhouse-McFarland/Monona

JoaquinRating, 5 stars1 month ago
Great location, quiet and private. We really appreciated how dog friendly the house was! Would recommend.
Guest favorite
A spacious living area features a cozy seating arrangement, including a leather chair and a sectional sofa. Large windows provide scenic views of the lake beyond, while a stone fireplace adds warmth to the wooden interior. A decorative table sits at the center on a patterned rug.
Home in Merrimac
5 out of 5 average rating, 13 reviews

Cody’s Cabin - Lake front property, Ski & Fish

BlakeRating, 5 stars10 months ago
Awesome place, very well maintained. Beautiful views.
Top guest favorite
A tranquil lake scene is captured at sunset, with vibrant colors reflected on the water's surface. Docked boats with covers are visible near a wooden pier, and the lush green grass in the foreground leads to the water's edge.
Home in Markesan
4.97 out of 5 average rating, 143 reviews

The Bluegill on Little Green Lake

SusanRating, 5 stars2 weeks ago
We loved the view of Little Green Lake from the dining area, and from the living room, and from right by water's edge on the small deck. Just so peaceful and beautiful! Enjoyed a few sunsets as well. Kitchen was well equipped, had everything you might need. House was located on a quiet road, so we were able to take several walks. Overall, we enjoyed our stay very much.
The exterior of the house showcases a spacious design with multiple windows and entrances. A large patio is visible at the back, surrounded by natural greenery and open grass areas. Several white chairs are positioned on the patio, inviting relaxation.
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!
The bedroom features a spacious bed adorned with an assortment of decorative pillows and a soft throw blanket. Nightstands on either side are accompanied by lamps, providing gentle lighting. A small potted plant adds a touch of greenery to the inviting space.
Home in Galena
4.8 out of 5 average rating, 5 reviews

Lakeview, newly renovated home

MichaelRating, 5 stars22 months ago
The location was great with a lake view. Very clean and well kept property. Instructions were very clear. The kitchen had everything we needed to prepare meals. Each bedroom was well furnished with comfortable beds. We would stay here again and recommend it to others. Thanks Rasa for making our stay part of a wonderful family trip by having a great rental property for us to use!
Two rustic cabins are nestled among tall trees, showcasing a warm wooden exterior. The cabin in the foreground has a visible balcony with a rustic railing, while a second cabin is seen in the background, illuminated by soft interior lighting.
Home in Wisconsin Dells

Quiet majestic Wisconsin Dells

A two-story house is depicted, featuring a dark exterior with a covered porch and a garage. Snow is visible on the ground, with some grassy areas peeking through. Trees are seen in the background, and a fire hydrant is positioned on the street in the foreground.
Private room in Hollandale

Eagle house

Family-friendly, ski-in/ski-out home rentals

A welcoming living area features vaulted wooden ceilings and ample natural light. Two comfortable leather couches surround a coffee table, and a dining table is positioned against the wall. Large windows reveal views of the outdoor deck and surrounding nature.
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
Two light-colored Adirondack chairs are positioned on a grassy area, offering a view of the lush surrounding landscape. Wildflowers and tall grasses are visible in the background, providing a natural setting. A cluster of trees stands nearby under a clear blue sky.
Apartment in Baraboo
4.87 out of 5 average rating, 276 reviews

Orchard Prairie B&B

DavidRating, 5 stars3 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 favorite
A wooden outdoor sauna is shown, featuring a rounded shape and a glass door. The structure is set among leafless trees, with a wooden deck leading up to the entrance. Natural wood tones provide a harmonious appearance in the peaceful surroundings.
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 favorite
A spacious sleeping area is showcased with a king bed dressed in soft linens and an earthy-toned coverlet. Decorative bedside lamps are positioned on each side, complementing the overall decor. Warm lighting from recessed fixtures gently illuminates the area.
Guest suite in Madison
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 favorite
A restored red cabin is set amidst a lush green lawn, surrounded by trees. Large windows provide natural light to the inviting interior. The sloping hills of the farm are visible in the background, creating a serene rural atmosphere.
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!
The exterior of the house showcases a spacious design with multiple windows and entrances. A large patio is visible at the back, surrounded by natural greenery and open grass areas. Several white chairs are positioned on the patio, inviting relaxation.
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!
A large outdoor swimming pool is surrounded by lounge chairs arranged neatly on the deck. Umbrellas provide shade for some seating areas. Lush greenery and trees are visible in the background, creating a serene environment.
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 favorite
A sandy beach area stretches along the tranquil shore of Lake Delton. White lounge chairs are arranged in neat rows, facing the calm water. Gentle waves lap at the edge of the shore, bordered by lush greenery and a stone embankment.
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
An aerial view of Chula Vista Resort showcases various water attractions, including colorful water slides and multiple outdoor pools. The surrounding area features lush greenery and lounge chairs for relaxation, while the resort buildings stand in the background against a clear blue sky.
Condo in Wisconsin Dells
4.77 out of 5 average rating, 75 reviews

Luxurious Chula Vista Retreat

WendyRating, 5 stars2 weeks 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
A spacious family room showcases a large gray sofa and a brown recliner, complemented by a coffee table on a decorative area rug. A flat-screen TV is mounted above an electric fireplace. Double doors provide access to the patio, allowing for natural light to fill the space.
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
The family room features leather seating that accommodates multiple guests and a warm electric fireplace. A large smart TV is mounted on the wall, with a wooden dresser and decorative art displayed nearby. Double doors lead to the patio, with natural light illuminating the space.
Condo in Wisconsin Dells

Dells Family Stacation-Lake Access-Hiking-Golf

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

Destinations to explore