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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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

4.8 out of 5 average rating, 49 reviews

Updated 3 bedroom in the UW Arboretum!

Setting like no other. Quiet Country Vibe yet in the Center of the City. Spacious & Updated w/wood floors, big windows, set across the street from trail thru wooded UW Arboretum! Big living room w/luxury furniture & work space is great for gathering. Or retreat to 2 big bedrooms on upper level. Plus big bedroom on ground level & a 4th sleeping area. All memory foam beds. Fully stocked kitchen. NEW: Windows, Siding, Roof & Flooring. Elevated deck off dining views lush yard w/fire pit & gas grill.

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.

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)

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, 178 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, 227 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.

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

🎯 WHAT'S INCLUDED: ✅ FREE Mini Golf ⛳& Canoes, Kayaks - 1st come, 1st serve ✅ Activity Center - see photos 🏊‍♂️ ✅ NEW Basketball Court 🏀 • Tennis 🎾 • Indoor Foosball & Pool 🎱 ✅ Fireplace, Sleeper Sofa, Patio ✅ TVs in Living Room & Bedrooms 📺 ✅ Fully Stocked Kitchen 🍽 ✅ FREE Laundry Onsite 🧺 (not in unit) 🚫 NO $25/NIGHT RESORT FEE like other places! 🧹 One-Time Cleaning Fee: $145 (paid to resort) 🌲 Only 20 mins from Devil’s Lake State Park (Baraboo) – 2 Beaches 🏖

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, 145 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.

Top 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

5 out of 5 average rating, 10 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.

Superhost

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, 107 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

4.78 out of 5 average rating, 92 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

4.74 out of 5 average rating, 73 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.

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

4.69 out of 5 average rating, 97 reviews

End of the road Lake House/ Super Quiet.

Best sunrises west of the Atlantic. Close to Madison (30mins), Milwaukee (85mins) and Chicago (120mins) Rustic cabin feel, Vaulted ceilings, Single over Full Bunk bed, queen, full and leather couch and room for air mattresses. Perfect for 1 to 8 guests. Super large shared backyard leads to the lake with a sandy beach. (unique property comprised of a 2br/1ba cottage and a house 2br/2ba joined together by a Great Room built to seamlessly connect the two)