
Ski-in/out vacation rentals in Madison
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Madison
Guests agree: these ski-in/out homes are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Madison ski-in/out rentals
Ski-in/out house rentals
Guest favourite

Home in McFarland
4.85 out of 5 average rating, 126 reviewsThe 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.

Private room in Albion
4.46 out of 5 average rating, 70 reviewsBeachkonong gr8 sunrise n shine
ChrisRating, 5 stars21 months ago
Michael was very kind and easy to communicate with.

Home in Galena
4.8 out of 5 average rating, 5 reviewsLakeview, newly renovated home
MichaelRating, 5 stars20 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!
Family-friendly, ski-in/out home rentals

Guest suite in Edgerton
4.71 out of 5 average rating, 95 reviewsEnd 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 reviewsOrchard 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 reviewsCountry 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 reviewsHospitality+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 reviewsGrateful 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 reviewsBeachkonong 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 reviewsChristmas Mountain Village Onsite SKI Tubing GOLF
DianaRating, 5 stars8 months ago
We loved loved our stay. Will definitely come back.
Ski-in/out condo rentals
Guest favourite

Condo in Wisconsin Dells
4.91 out of 5 average rating, 96 reviewsLakefront Condo - Private Beach | Boat Slip| Pool
DusanRating, 5 stars4 months ago
Amazing place .highly recommend!!
Superhost

Condo in Wisconsin Dells
4.77 out of 5 average rating, 69 reviewsLuxurious Chula Vista Retreat
TaylorRating, 5 stars3 weeks ago
The condo was perfect for the 2 families who went to the Dells. They had games for the family and the kids had a blast!
Superhost

Condo in Wisconsin Dells
4.77 out of 5 average rating, 35 reviewsDells Paradise - Lake Access with Boat Slip
MattRating, 5 stars1 month ago
awesome! would definitely recommend and stay again!
Superhost

Condo in Wisconsin Dells
New place to stayDells Family Stacation-Lake Access-Hiking-Golf
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- Wilderness Territory
- Chula Vista Resort Water Parks
- Wild Rock Golf Club
- Kalahari Resorts Wisconsin Dells
- Devil's Lake State Park
- Noah's Ark Waterpark
- Devil's Head Resort
- Lake Kegonsa State Park
- Mirror Lake State Park
- Mt. Olympus Parks, Outdoor Theme Park
- Henry Vilas Zoo
- Yellowstone Lake State Park
- Mt. Olympus Parks, Parthenon Indoor Theme Park
- Cabin 857-1- Christmas Mountain Village
- Lost World Water Park
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- Cascade Mountain
- Wisconsin State Capitol
- Tom Foolerys Adventure Park
- Extreme World
- Alligator Alley
- Tyrol Basin
- Klondike Kavern Water Park
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