Ski-in/Ski-out holiday rentals in Madison

Top Guest favourite

Guest favourite

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.

Top Guest favourite

Guest favourite

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.

Glacier Canyon Waterpark Dells

The Club Wyndham Glacier Canyon in Wisconsin Dells, the ultimate family vacation resort. Enjoy indoor and outdoor water parks, a lazy river, hot tubs, pools, arcade games, mini golf, golf courses, fitness center, dining, bar, pool bar, barbecue areas, walking trails, and more. Perfect for families, couples, and groups looking for fun, relaxation, and unforgettable memories. Spacious resort comfort after long travel days. Book early, prime vacation dates fill fast for this top Dells destination!

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 favourite

Guest favourite

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 heat, is air conditioned, has a small kitchenette, bathroom with shower, and wireless high-speed 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.

Dells Resort | Free Mini Golf + Kayaks + Pools

🎯 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 🏖

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.

Lakefront Condo - Private Beach | Indoor 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.

Family Staycation-Pool Beach Golf Pickle Ball

Upgrade to the Noah's Ark & Land Of NATURA Waterpark Packages after booking! See below for details. Immaculate 2-Bedroom 2-Bathroom condominium Optimally situated in Lighthouse Cove. This single-level, ground floor property offers comfort and style. Enrich your living experience being merely 40 feet away from a gorgeous outdoor pool, or simply take a quick stroll over to our indoor pool, situated 120 feet away. Beach lovers are less than 500 feet from sun-soaked paradise.

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 restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Mt. Olympus, 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!

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.

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.