All set to visit America’s Dairyland? Wisconsin is home to dairy farming and supplies more than 15 percent of the total milk production in the country. As a result, it is also the top cheese producer in the US, usurping 90 percent of the state’s milk supply in making cheese. No wonder Wisconites are lovingly called Cheeseheads. However, milk and cheese are not all that you will find here. Wisconsin is also home to marvelous streams, rivers, and lakes, making watersports popular in the area. Also, the state experiences long winters and snow aplenty, making it a paradise for skiers. Beginners can root for the upscale resorts near major cities to polish their skills whereas seasoned skiers can head farther south for adventure. No matter what your skill-set is, you would need a great stay to rest your tired body after a day of skiing. So go ahead and find out the best ski-in ski-out accommodations in Wisconsin, USA.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on October 24, 2025.
1. Grand cabin for 15
Have a grand vacation by staying in this amazing ski-in ski-out cabin located close to Devil’s Head Ski Resort. It is also a short drive from many points of interest around the city. Beautifully furnished, the cabin is thoughtfully designed to exude an inviting ambiance. There are three floors featuring excellent amenities. It includes five bedrooms, two full bathrooms, a half bath, air conditioning, free internet, television, and lounging areas. Since this is within a peaceful landscape, guests are encouraged to take a stroll around the area.
Baraboo, Wisconsin, United States
165.25 km (102.7 mi) from Rib Mountain State Park
Top guest reviews
Host:
the owners take great pride in their home and it showswe thoroughly enjoyed our stay and the owner was a pleasure to deal withthe owners were also extremely conscientious is making sure we had firewood access codes you name itLocation:
a great property in a great location being close to the dells and devil's lakeperfect location lots to dowe loved this cabin for our cousin getaway weekend it was in the perfect locationolyna’s cabin is fantastic place we hope to return to each yearCleanliness:
there were plenty of blankets for the chilly nights and the home was extremely cleanbig clean awesome house thoroughly enjoyed our stay at the cabin in spite of the wet weekendRead more reviewsAmenities & Room:
beautiful property with plenty of room for our groupit was warm cozy and well equipped for friends and family to chill togetherextremely comfortable and well maintained
2. Lakefront home with boats provided
In this accommodation, guests can make use of great amenities including a paddleboat, six kayaks, two canoes, a pool table, an electronic dartboard, two grills, and so much more. It comfortably houses up to 12 guests. The home is spacious and has four bedrooms and two bathrooms. The sunsets are perfect for some barbecue and wine at the outdoor lounge. Stroll around the woods to discover more amazing spots. The property offers access to cross-country ski on Lower Gresham Lake and water channels that helps join the other lakes.
Arbor Vitae, Wisconsin, United States
124.6 km (77.5 mi) from Rib Mountain State Park
Top guest reviews
Host:
owners are very responsive to any questions and needsLocation:
beautiful location on a small private lakevery nice property in an excellent location with plenty of privacyCleanliness:
everything was clean and beautifulit was very cleanthe house was very clean and we would love to come back again next yearall the amenities one could want; very clean and comfortableRead more reviewsAmenities & Room:
the beds were a little overly soft but otherwise everything was fantastic
3. Lakeside cottage with pontoon boat
This property is situated just right beside Pickerel Lake, watersports are accessible. Cross country ski area can be accessed across the lake and it also offers private access to trails in the wooded areas. Just by the water’s edge, there is a fire pit and some seats, perfect for recreation. The tranquility here is notable since the nearby road is less traveled and the property has its own secluded bay. Up to nine guests can comfortably stay here since there are three spacious bedrooms and a bathroom, among many other amenities.
Pickerel, Wisconsin, United States
80.77 km (50.2 mi) from Rib Mountain State Park
4. Grand home in a quiet neighborhood
Expect a tranquil stay in this grand home for eight guests. Located close to Granite Peak Ski Resort which is a part of Rib Mountain State Park, one can access major skiing trails that boast a height of 700 feet (213 meters). The retreat is spacious and it includes formal dining rooms and living rooms, a kitchen with full appliances, an entertainment area, laundry facilities, two garages, three bedrooms, two bathrooms, a half bath, and air conditioning. Take note that guests can stay for three nights at the minimum.
Wausau, Wisconsin, United States
1.24 km (0.8 mi) from Rib Mountain State Park
Top guest reviews
Host:
karen was an awesome host as wellkaren is very caring and helpful hostkaren (owner) was very helpful welcoming and responsivekaren was very helpful and responsive to our questions and needseach time the place was comfortable and accommodatingLocation:
had a wonderful close to skiing get awayclose to local stores and restaurants and was able to sleep eight of us comfortablylocation cannot be beaten for skiing at wausauit was a great location for us being less than a mile to granite peakCleanliness:
house was clean and spaciousthe house is amazing and impeccably cleanthe house was very spacious and super cleanit was clean cozy and super convenient to granite peakthe house was clean and had all we needed to have a great timeRead more reviewsAmenities & Room:
comfortable beds full kitchen washer dryersuper comfortable for 4-6 people and space to spread outthe main lounging area has comfortable couches the tv and kitchen area is open and usablethere is only one shower but that never was a problem for our entire groupthe house was in excellent condition was spacious and yet still warm and cozy
5. Beautiful home in the woods
This home is within walking distance of beautiful sceneries such as Serenity Bay. Many outdoor activities such as fishing, boating, and skiing can be easily accessed here. Spend a lovely afternoon on the deck while making some delicious barbecue with the gas grill. Inside, there is a fireplace, large dining area, fully equipped kitchen, sauna, and five bedrooms. This is an ideal retreat for family and friends since up to 16 guests can stay here.
111.37 km (69.2 mi) from Rib Mountain State ParkAccommodates: 16
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
jason was very easy to get a hold of and a great hostjason was easy to work with and very responsive to any questionsthe property owner jason was awesome very accommodating and always answered his e mails right away everythingjason was responsive and the house had so much to offerLocation:
so cute and the location was perfectperfect location for ice fishingbeautiful house in a perfect location for hitting the trailsthe property is in a very good location with access to boating fishing golfing biking and walking trailswe were able to walk right out on the ice and enjoy the dayRead more reviewsCleanliness:
house was very clean and well stockedhad plenty of room and very cleanthe house was clean and spacious for our group of 16very clean nice getaway we’re there for a week and did not want to leavewas there with 8 people snowmobiling and everyone complimented on how roomy and clean the house was
6. Secluded retreat by the woods
Surround yourself with nature and stay in a retreat in the woods. To get here, keep driving until you reach almost the dead end on the road near the forest reserve. This beautiful accommodation is heavily surrounded by tall trees and has a great view of the lake. Many amazing water activities such as boating, swimming, are accessible here. American Birkebeiner Trail is 17 mi (27 km) away from the property but that doesn’t take the acommodation’s credibility away.
208.83 km (129.8 mi) from Rib Mountain State ParkAccommodates: 7
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
our host was excellentcraig (owner) was very helpful and prompt answering questions and providing informationthe owners are unobtrusive but you still feel like you’re on their propertyit was an overall great experience and craig was nothing but a great hostcraig was helpful and friendly we would visit againCleanliness:
the cottage was clean and modern with many conveniencesRead more reviewsAmenities & Room:
really enjoyed our stay here the queen bed has a very good mattresscabin very comfortable with a well equipped kitchen plus the barbecue outside
7. Peaceful home with a private dock
This inviting home is located by Brule River, which is famous for its natural beauty and cross-country skiing trails. However, guests have to bring their skiing equipment. They can make use of the fully equipped kitchen, internet, television, three bedrooms, and two full bathrooms to stay comfortably. Nature lovers and fishermen would surely adore this retreat because of its location and amenities.
229.88 km (142.9 mi) from Rib Mountain State ParkAccommodates: 6
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 14 days before check-in.
Top guest reviews
Host:
the owner is very easy to work withthe owner has been a good steward of caring for this propertythe caretaker was very nice and available when neededLocation:
beautiful location lovely well-kept property responsive ownersRead more reviewsCleanliness:
clean comfortable beautiful spacious housethe bathrooms were newly renovated and cleanit was very rustic but clean and modernized at the same time
8. Lakehouse with pontoon
One of the best ways to have fun in Wisconsin is skiing. This lakehouse is just beside Trego Lake. In winters, this lake offers loop routes for skiers, beginners to professionals. Up to 10 guests can comfortably stay in this lakehouse. Other amenities included are four bedrooms, three bathrooms, internet, air conditioning, a fully equipped kitchen, and lounging spaces both inside and outside.
Trego, Wisconsin, United States
201.44 km (125.2 mi) from Rib Mountain State Park
Top guest reviews
Host:
property manager was very responsive to our questions and followed-up to make sure we had everything we neededthe owners were also very welcoming and willing to help if we needed anythingcj the property manager was helpful professional pleasant and responsive to any questions or needsneighbors were very nice and accommodating as wellwe met the neighbors who were very friendly (and quiet)Location:
clean place great location looking forward to going back this summerCleanliness:
this property was amazing clean & beautifully decoratedclean beautifully maintained spacious and you could even hear the call of loons right out the doorRead more reviewsAmenities & Room:
we had 10 people (6 adults and 4 kids) stay here and it was very nice and comfortable
9. Beautiful chalet on flat terrain
Get easy access to cross-country skiing trails from this gorgeous private accommodation. Those looking forward to trying out outdoor activities in Wisconsin will find this home ideal. From here, take a walk to explore the gardens, forests, or the gorgeous Granite Peak, the best spot for skiing in the Midwest. Have a restful time at this property that has four bedrooms, two bathrooms, a half bath, a kitchen with appliances, and lounging areas. Expect a tranquil stay in this spectacular property.
Wausau, Wisconsin, United States
12.61 km (7.9 mi) from Rib Mountain State Park
Top guest reviews
Host:
doris is extremely responsive and helpfulthe hosts were great with their communication prior to our stayLocation:
reasonably close to grocery stores and other shopping as well as recreational opportunitiesCleanliness:
beautiful clean and roomywe found the house beautiful very clean comfortable & spaciousthe house is very nice clean and exactly as describedthe house was very clean and beds were super comfortablethis house is very spacious clean with a great layoutRead more reviewsAmenities & Room:
we enjoyed the fireplace while playing cards at the kitchen tableso much room to spread out and enjoyed sitting out in the yard and playing
An engaging winter vacation
Skiing and many other winter sports keep residents and visitors engaged. One can participate in these fun activities for an exciting and memorable stay. Take time to explore even more places around to discover hidden spots. Also, witnessing the festivities around Wisconsin such as Northwoods Blizzard Blast would be ideal.
For more places to stay, check out some treehouse hotels and vacation rentals in Wisconsin.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data