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.

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Guest favorite
A vibrant yellow A-frame cabin is nestled among greenery, featuring large windows and a deck. In the foreground, a group of sheep is seen walking along a gravel path, adding a rustic charm to the serene landscape.
Tiny home in Highland
4.91 out of 5 average rating, 45 reviews

Cheese Wedge Cabin Idyllic Farm

Celebrate Wisconsin’s cheese heritage in this award-winning, A-Frame cabin, shaped like a wedge of Swiss cheese! Enjoy a peaceful getaway on this idyllic sheep farm. Live simply, unplug and decompress. Wake to the sound of morning birdsong, sit under the stars by the firepit at night. Fish in the class II trout stream. Walk the trails in the woods. Cabin has no wifi, no water, and solar-powered electricity. Access to wifi service and your own private bathroom and kitchen is a short walk away.

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, 154 reviews

The Bluegill on Little Green Lake

This charming 3 BR house on Little Green Lake is perfect for relaxing, or as a great home base for recreational activities all year round -fishing, golf, and water sports in the summer, snowmobiling, x-country skiing and ice fishing in the winter. Little Green is located in Green Lake County, WI. This lake is 462 acres in size and is 28 feet deep at its deepest point. It is a Class A Muskie lake and anglers can expect to catch a variety of fish including Bluegill, Bass, Northern and Walleye.

Superhost
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

PLEASE BOOK VERY FAR & EARLY AS SPACE IS LIMITED Entire Cabin, cottage, villa, timber or townhome, vary based on availability @ booking. AMENITIES For All Units (Seasonal) Basketball Billiards Canoes/Kayaks Kids Pool Clubhouse Fishing Fitness Room Game Room Mini & Golf Grocery/Convenience Store Indoor Pool Outdoor Heated Pool Paddle Boats Playground Restaurant Snow Skiing Tennis Volleyball AREA ATTRACTIONS Boat Tours of The Dells Indoor/Outdoor Waterparks State Parks (Hiking, Fishing & Boating)

Top 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 Midvale Heights
4.92 out of 5 average rating, 179 reviews

Hospitality+Kitchen+Laundry+Gardens

Tastefully updated private suite on lower level of ranch. - KING bed plus twin bed, large bathroom, full kitchen, laundry W/D, work desk, dining table w/stools, comfortable furniture. Pristine clean. Close to grocery, many restaurants, parks, UW... Great for business needs (week and month long discounts!), moving to Madison, athletic events, visiting family... Tree lined street. Free parking. Owner lives on the property, but suite is private and not shared, as per Permit #ZTRHP1-2020-00004.

Guest favorite
A charming red cabin is nestled among lush greenery, showcasing large windows that invite natural light. A white porch with comfortable seating overlooks the well-maintained yard. A red barn is visible in the background, surrounded by grass and trees.
Farm stay in Plain
4.95 out of 5 average rating, 230 reviews

Grateful Farms Cabin: Hills, Creek, Gorgeous Views

Fully-renovated 1890s cabin located on a 60+ acre farm just north of Spring Green. The cabin has radiant floor heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless internet. The farm has a barn from 1895, a main home built in 1923, apple trees, hiking trails, creek with a swimming hole, and a large hill with marvelous views. Make this your private weekend cabin or a longer-term retreat. Farm powered primarily by a large solar array atop one of the barns.

Superhost
A spacious room features a King bed with a sleek headboard, complemented by vibrant decorative pillows. A pair of cozy armchairs is positioned beside large windows, and wooden beams add character to the ceiling. A neutral color palette enhances the inviting atmosphere.
Apartment in Lake Geneva
5 out of 5 average rating, 8 reviews

The Eastpoint Suite 2| Walk to the Lake & Town

The Eastpoint offers meticulously designed rooms that showcase a stunning mid-century modern aesthetic, blending timeless elegance with modern comforts. Located within walking distance of both the lake and downtown Lake Geneva, our boutique lodging invites you to be among the first to enjoy while we continue to build out a destination that will soon be recognized as Lake Geneva's newest and most exciting hotel experience. Room 2 features a King bed, cozy seating area and spacious bathroom.

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, 152 reviews

The little Green Birdhouse-McFarland/Monona

Adorable tiny house located just 1/2 block to Lake Waubesa with public lake access. It's a 1/2 mile walk to the Yahara bike path, access to the Capital City bike path and into downtown Madison. Spacious, open living room. Open concept kitchen with butcher block countertops. One bedroom with an attached full bath. Laminate hardwood floors throughout. 2 car parking pad. Large backyard with a firepit, brand new fence, and a nice view of the lake. The neighborhood is quiet and welcoming.

Guest favorite
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
4.88 out of 5 average rating, 17 reviews

Dells Family Stacation-Lake Access-Hiking-Golf

NEWLY REMODELED & PARTNER DISCOUNTS FOR THE GUESTS: 1. TWO MT. OLYMPUS WATER PARK PASSES INCLUDED WITH A MINIMUM OF 4 NIGHT STAY. 2. TWO SPLASH PASSES INCLUDED WITH EACH STAY, BUY 1 GET 1 DEAL FOR NATURA WATER PARK PASSES & MORE. EXCLUSIVE DISCOUNTS FOR GOLF, ADVENTURES, WATER PARKS, RESTAURANTS & THEATER Dells Stacation is recently remodeled & located in Lighthouse Cove Condos: 40 feet to the outdoor swimming pool, 120 feet from the indoor pool and less than 500 feet to the beach.

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
4.89 out of 5 average rating, 111 reviews

Lakefront Condo - Private Beach | Boat Slip| Pool

Experience lake life at our luxury, lakefront condo. Wake up to morning coffee on the balcony with breathtaking views of Lake Delton. Our spacious 2 bedroom, 2 bathroom condo features a beautiful master suite with a king bed, en suite bathroom complete with a jetted massage tub and walk in shower with 3 directional shower heads. It is the perfect escape for those who want to feel like they are a world away, but are also minutes from all the fun and excitement of the Dells.

Guest favorite
This vibrant indoor water park features several water slides of varying heights and twists, surrounded by playful structures. Shallow pools for children and lounging areas are visible, while guests engage in water activities. Lush tropical landscaping enhances the fun environment.
Condo in Wisconsin Dells
4.79 out of 5 average rating, 98 reviews

Luxurious Chula Vista Retreat

No resort fees! Experience all the Wisconsin Dells has to offer while staying in this luxurious condo, located inside the action-packed Chula Vista Resort! Enjoy the resort's waterparks, restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Noah's Ark and hiking trails! Then relax in our Jacuzzi tub, cozy up to our two fireplaces, hang out in our spacious living room or cook a family meal in our full-size kitchen!

Superhost
The exterior of the townhouse is shown, featuring warm orange siding and a sloped roof. A wooden ramp leads to the entrance, surrounded by greenery. A seasonal wreath adorns the door, emphasizing a homey feel. Pine trees are visible in the background.
Townhouse in Dellona
4.73 out of 5 average rating, 74 reviews

Private Townhouse at Christmas Mountain

Our 3 Bedroom Townhouse on the grounds of Christmas Mountain offer a peaceful place to spend quality time on vacation with friends and family. There is plenty of room to spend time together and still have space for private time. In The living room we have provided you with a flat screen tv with a firestick attached for your entertainment. Off the living room is a covered porch for your enjoyment day and night. There is fiber internet providing you with high speed wifi.

Superhost
A circular, above-ground swimming pool with clear, inviting water is visible, surrounded by lush greenery. The pool deck features wooden planks, and a set of steps leads into the water, creating easy access. The tranquil lake can be seen in the background.
Home in Montello
4.81 out of 5 average rating, 48 reviews

3bed lake house, private pool near WI Dells

Relax with the whole family at this peaceful pool lakeside home. If you enjoy kayaking, paddle boating, fishing/ice fishing or taking a dip in a pool then this place is for you! This home offers so many activities for the whole family to enjoy. Relax on the wrap around house deck with it’s own fireplace, grill, outdoor dinning or lounge area. Looking for a little more activity, head over to the pool deck, basketball court, or challenge your family to a yard game.

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

Quick stats about vacation rentals that are ski-in ski-out in Madison

  • Nightly prices starting at

    Madison vacation rentals start at G$29,240 GYD per night before taxes and fees

  • Verified guest reviews

    Over 690 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madison rentals

  • 4.8 Average rating

    Madison stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Madison's top spots, include Henry Vilas Zoo, Wisconsin State Capitol, and Olbrich Botanical Gardens

Destinations to explore