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

4.78 out of 5 average rating, 46 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

The A-Frame cabin is perched on a wooden deck, showcasing its bright yellow exterior and triangular windows. A cozy seating area with a chair and small table invites relaxation in the outdoors, surrounded by greenery and a tranquil atmosphere.

Tiny home in Highland

4.93 out of 5 average rating, 42 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 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 Madison

4.91 out of 5 average rating, 171 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 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, 207 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.

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

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. A brand new 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.

Superhost

Condo in Wisconsin Dells

4.77 out of 5 average rating, 35 reviews

Dells Paradise - Lake Access with Boat Slip

DELLS VACATIONS CLUB SPECIALS: 1. BOOK 4 NIGHTS OR MORE & GET 2 MT. OLYMPUS WATER PARK PASSES 2. TWO FREE SPLASH PASSES, OFFERING OVER 70 BUY 1 GET 1 DISCOUNTS. 3. EXCLUSIVE DISCOUNTS FOR GOLF, ADVENTURES, WATER PARKS, RESTAURANTS & THEATER This Dellsvacations club property is located in Lighthouse Cove on Lake Delton offering everything for a perfect vacation. Enjoy beach, lake, trails, swimming, golf or soaking in the hot tubs. Experience the perfect blend of relaxation and fun.

A cozy lounge area is highlighted by a leather sofa facing a rustic stone fireplace. Wooden beams are visible on the ceiling, and a coffee table rests on the warm-toned wooden floor. Large windows provide views of the indoor space, enhancing the inviting ambiance.

Cabin in Wisconsin Dells

4.73 out of 5 average rating, 89 reviews

Christmas Mountain Village Onsite SKI Tubing GOLF

The best kept secret in the Dells! 4MI - the waterparks, expwy, Walmart. Full kitchen and cooking items too! See photos. Free mini golf, kayaks, canoes. First come first serve. *****NO $25/night tax ***There is $145 cleaning fee charged by the resort at checkin. *** My unit is in the best location on the property! Near Activity Center, Main outdoor pool, basketball, Volleyball, Restaurant, laundry. 4 outdoor pools/ hot tubs at the resort. 1 indoor pool, sauna, workout room.

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

4.91 out of 5 average rating, 96 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.

Superhost

An open-concept living area features a dining table with metal chairs and a comfortable seating arrangement, including a sofa and recliner. A well-equipped kitchen is visible in the background, and soft lighting from multiple sources creates a warm ambiance.

Condo in Wisconsin Dells

4.78 out of 5 average rating, 67 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

A serene outdoor hot tub area is presented, featuring two interconnected tubs surrounded by a stone edge. Smooth, natural rocks are arranged around the tubs, and a fenced area with trees provides a sense of privacy. The sky appears slightly overcast.

Townhouse in Dellona

4.73 out of 5 average rating, 60 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

4.71 out of 5 average rating, 95 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)

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

Welcome to my home - Orchard Prairie Air B&B! This unique space was built by an amateur pilot, "MacGyver-Type," Renaissance Man roughly 30 years ago. It is set on 38 acres of pristine Wisconsin Land and is perfect for nature lovers and "Glampers" looking for the great outdoors with the comforts of home. It is a "rustic-industrial" oasis in the heart of South Central Wisconsin, steps from Devils Lake and miles from Baraboo and the Wisconsin Dells.