Ski-in/Ski-out holiday rentals in Madison

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.

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.

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.

-Buffalo Lake House-

Welcome to our Buffalo Lake house, located 25 miles northeast of Wisconsin Dells and 20 miles north of Cascade Mountain ski resort. This spacious four-bedroom retreat comfortably accommodates up to 6 guests, making it ideal for families and friends. Immerse yourself in nature, where adventure and tranquility meet. While Buffalo Lake isn't suitable for swimming, it offers relaxation and activities such as fishing and kayaking. We can't wait to host you and your family for an unforgettable stay!

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.

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.

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 | 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.

Dells Paradise : Jacuzzi, Pool & Hot Tub

Welcome to Dells Paradise, a luxurious vacation rental located in the picturesque Lighthouse Cove on Lake Delton. A property, managed by Dellsvacations Club, offers everything you need for a perfect getaway. Imagine waking up to the sound of waves crashing on the sandy beach, strolling through scenic trails, and taking a refreshing swim in the crystal-clear lake. And that's just the beginning. A spacious one-level condominium, an ideal vacation spot for families and friends.

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!

3bed lake house, private pool near WI Dells

Relax with the whole family at this peaceful pool lakeside home. If you enjoy kayaking, paddle boating, fishing/ice fishing or taking a dip in a pool then this place is for you! This home offers so many activities for the whole family to enjoy. Relax on the wrap around house deck with it’s own fireplace, grill, outdoor dinning or lounge area. Looking for a little more activity, head over to the pool deck, basketball court, or challenge your family to a yard game.

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.