Ski-in/Ski-out vacation rentals in Madison

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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

An inviting living area features a spacious arrangement of comfortable sofas, accented by decorative pillows. A carpeted floor enhances the cozy atmosphere, while natural wood beams and polished ceiling add character. A view into a well-appointed kitchen can be seen in the background.

Barn in Waukesha

4.99 out of 5 average rating, 71 reviews

Willow Springs Loft @ Wern Valley

Looking for that beautiful once in a lifetime opportunity to sleep in the hay loft? Look no further. No expense has been spared in the space. It is beyond beautiful with every rustic feel you can think of, yet extremely classy. Railings made from cattle stanchions, shower heads that are watering cans and sinks from wash tubs. The evening view of deer and turkeys in the valley from your 30 foot deck is priceless. Ride your ATV to Wern Valley Sportsmen’s Club for a pheasant hunt or clays shooting.

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

4.91 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.

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, 151 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.

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 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

4.95 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.

Guest favorite

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, 6 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, 146 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

Condo in Wisconsin Dells

5 out of 5 average rating, 13 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, 108 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, 94 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, 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.

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)