Ski-in/Ski-out vacation rentals in Madison

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

Top-rated ski-in/ski-out rentals in Madison

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

An inviting living area features a spacious arrangement of comfortable sofas, accented by decorative pillows. A carpeted floor enhances the cozy atmosphere, while natural wood beams and polished ceiling add character. A view into a well-appointed kitchen can be seen in the background.

Barn in Waukesha

5 out of 5 average rating, 62 reviews

Willow Springs Loft @ Wern Valley

DavidRating, 5 stars5 months ago

The hosts are very friendly and responsive. It truly is a working farm with animals and knowledgeable and helpful hosts. Our kids had a great time with the animals and the host. The stay/house itself is very cool and well decorated. Lots of great little touches and decor. We’re very glad we chose to stay at and experience this home.

Superhost

A spacious living room is shown, featuring a large brown leather sectional sofa positioned towards a flat-screen TV. Wood flooring is present, complemented by natural light from a nearby window and soft lighting from a floor lamp. An accent chair and side tables add to the inviting layout.

Townhouse in Madison

4.78 out of 5 average rating, 46 reviews

Updated 3 bedroom in the UW Arboretum!

ErnestRating, 5 stars13 months ago

Came to Madison on a 4 month work trip with 4 coworkers. The accommodations were just right for my group and Doug also contacted us various times to during our stay to make sure everything was as we needed it. I would not hesitate to contact Doug in future if I'm back in Madison.

Guest favorite

A fully-renovated cabin, painted red, is surrounded by a blanket of freshly fallen snow. The sloped roof is covered in snow, and the porch features a white railing. Leafless trees frame the cabin, creating a serene winter landscape.

Farm stay in Plain

4.94 out of 5 average rating, 208 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

LisaRating, 5 stars1 day 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

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

4.85 out of 5 average rating, 126 reviews

The little Green Birdhouse-McFarland/Monona

ShelbyRating, 5 stars3 weeks ago

My wife and I had a great stay at the Little Green Cottage. The neighborhood is just fantastic. A beautiful lake and Nora keeps a nice yard. The neighborhood is lively with activity during the day and very calm and quiet evening and night.

Vacation rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

Guest favorite

Home in McFarland

4.85 out of 5 average rating, 126 reviews

The little Green Birdhouse-McFarland/Monona

ShelbyRating, 5 stars3 weeks ago

My wife and I had a great stay at the Little Green Cottage. The neighborhood is just fantastic. A beautiful lake and Nora keeps a nice yard. The neighborhood is lively with activity during the day and very calm and quiet evening and night.

Guest favorite

A large cabin is situated on a hillside, featuring expansive windows and a balcony. A stone staircase, flanked by lush greenery, leads up to the entrance. The warm glow from the windows suggests a welcoming interior.

Home in Merrimac

5 out of 5 average rating, 13 reviews

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

BlakeRating, 5 stars9 months ago

Awesome place, very well maintained. Beautiful views.

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

4.46 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.

Show all

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 stars17 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, 272 reviews

Orchard Prairie B&B

TomRating, 5 stars6 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 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, 366 reviews

Country cabin, birders paradise.

AmandaRating, 5 stars2 weeks ago

We loved this little cabin in the woods. It was a charming experience with excellent hosts. Gwen and Ed are dedicated members of their community. They kindly told us in advance about the charity egg hunt and invited us to attend. The home was spotless and solar powered, all excellent choices. We would return in the future. Do not hesitate to book this home -- it is close to Madison, but yet so far away.

Top guest favorite

Guest suite in Madison

4.91 out of 5 average rating, 171 reviews

Hospitality+Kitchen+Laundry+Gardens

RachelRating, 5 stars3 months ago

Mary’s place was exactly as described. Comfortable bed, spacious area, fully stocked kitchen/bathroom, and very clean. Mary is a very kind and accommodating host. 100% recommend!

Guest favorite

Farm stay in Plain

4.94 out of 5 average rating, 208 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

LisaRating, 5 stars1 day 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