Ski-in/Ski-out holiday 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

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 favourite

Tiny home in Highland

4.93 out of 5 average rating, 43 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.

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 favourite

Guest suite in Madison

4.91 out of 5 average rating, 175 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 favourite

Farm stay in Plain

4.95 out of 5 average rating, 221 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 favourite

Home in McFarland

4.84 out of 5 average rating, 140 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.

Superhost

Condo in Wisconsin Dells

4.82 out of 5 average rating, 45 reviews

Dells Paradise - Families & Beach Lovers

GIFTS 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 Paradise is located 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.

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 favourite

Condo in Wisconsin Dells

4.88 out of 5 average rating, 103 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

Condo in Wisconsin Dells

4.76 out of 5 average rating, 82 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

Townhouse in Dellona

4.73 out of 5 average rating, 70 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.

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)