Vacation rentals in Cascade Mountain

*NEW OWNR SPECL Private Getaway w/ Sauna + Hot Tub

Atop the hills of the Town of Caledonia surrounded by woods, a true escape for some R&R. Some of the best skiing in the area, both Cascade Mountain & Devil's Head within minutes! Expansive floor-to-ceiling windows w/sunset views. Outdoor spaces surrounded by nature, indoor hot tub & sauna, plus rec area for enjoying games by the LL wet bar. Covered patio & firepit to warm up. Close to WI Dells, Baraboo, Portage, a perfect retreat for a peaceful getaway for the whole family or a romantic getaway!

Family · Location · Comfort

Peaceful, Handcrafted Retreat on WI River

Find rest, quiet, & connection to nature in our contemporary approach to a rustic retreat, set on 2 acres w/ 250 feet of WI River waterfront. Cathedral-like ceilings invite sunny mornings & community around a massive slab table. The custom kitchen island, coffee-bar, hand-poured concrete sinks, amish shiplap, kid's nook, cozy loft, timber-built bunk bed, hardwood floors, & more were designed to create a comfortable, unique, & welcoming experience that leaves guests refreshed & excited to return.

Family · Location · Layout

Crown Lodge, Baraboo Bluffs

Nestled deep in the Baraboo Bluffs on a dead-end country road. A true cabin-in-the-woods feel without sacrificing space or amenities. Perfect for family getaways, outdoor enthusiasts, or anyone craving a peaceful recharge. Whether you’re sipping coffee or drinks on the deck while watching wildlife, hiking the bluffs, skiing nearby or visiting the Dells, there’s no shortage of things to do, or not do! Minutes from Devil’s Lake, Devil’s Head Resort, Ice Age Trails & 25 minutes to Wisconsin Dells

Family · Location · Check-in

Secluded WI River Getaway w/ Hot Tub near Golfing

Get away from daily routines & refresh by the Wisconsin River at your private & peaceful retreat located near Devil's Lake, Cascade Ski & Devil's Head Ski/Golf Resorts & WI Dells. Perfect for families w/ 9 beds, 8 person Hot Tub, 6 Kayaks (May-Oct), Ping Pong, Foosball, Darts & Outdoor Games. The modern spacious design is filled w/ natural light, luxury comforts & new furnishings w/ Chef’s Kitchen, Weber Grill, Fireplace & Solo Stove. Ask us about nearby River Islands or day trips to ski/hike.

Location · Value · Getting around

Fall Woods Retreat Near WI Dells & Devil’s Lake

Fall brings hiking trails, wildlife sightings, and evenings under the stars. This peaceful 2.5-acre retreat near Wisconsin Dells and Devil’s Lake is perfect for families, nature lovers, and creative escapes. Enjoy a Pac-Man arcade, electric fireplace, indoor/outdoor games, yoga mats, and a dedicated workspace. Baby-friendly amenities included. With 3 bedrooms (sleeps 6), high-speed Wi-Fi, and a private deck with BBQ grill and fire table, it’s the perfect home base for your next getaway.

Location · Family · View

Modern Riverview Cabin Near Devil’s Lake

Reconnect w/ nature in this beautiful modern cabin set on 2 acres overlooking the WI River. Located near Devil's Lake, WI Dells, Devil's Head and Cascade ski resorts, it is the perfect place to unwind. Bedrooms have a king bed, queen bed and four bunk beds - each w/ ensuite bathrooms. Given the bedroom w/bunk beds, we approve 6 adults or up to 8 if 2 are children. Enjoy camp fires around a Solo Stove and grilling on the charcoal Solo Stove Grill. This cabin is new w/new furnishings.

Value · Location · Hiking

Grandma's House: Summer Vacation Time!

Welcome to Grandma's House, a single level home nestled in the beautiful hills of Caledonia, between Portage and Baraboo. Three bedrooms, sleeps 8, full kitchen, dining room, living room and an attached 2-car garage. Just 4 miles from I90/94, Grandma's House enjoys easy access to Portage, Baraboo and Wisconsin Dells. Renovations include, new vanity mirror in bathroom, new queen hide-a-bed with memory foam mattress (no bar at the back), and new queen bed with pillow- top mattress.

Value · Family · Comfort

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

Family · Value · Outdoor spaces

Green Door Getaway

Take a moment. Make yourself a cup of coffee in the bright kitchen. Find a cozy corner to read a good book. Grab the yoga mat and get your workout in while you stay. Spread out at the desk and finish your project. Connect with family and friends in the spacious living and dining areas. Enjoy a hike at a nearby State Park. Take in the thrills in the Dells. Ski down Christmas Mountain, Devil's Head or Cascade. Maggie's Green Door Getaway is ready for you to enjoy!

Location · Family · Wifi

Sweet Farmhouse Retreat - Sun-Drenched Porch!

Historic farmhouse on a working livestock farm! Enjoy river valley views, peaceful sunporches, and likely sightings of our Belted Galloway cows & sheep. Top Nearby: ~Devil’s Lake (13mi) & Wisconsin Dells (23min) ~Skiing: Cascade (9mi) & Devil’s Head (7mi) ~Wollersheim Winery & Lake Wisconsin Relax by the firepit under the stars. 3 cozy bedrooms (Queen on main; Double/2 Twins up). Historic charm meets modern comfort. Minutes from everything, yet worlds away!

Value · Location · Access

Peacocks and Luxury on 100+ acres, Hot Tub, Sauna

This is a true country estate. Luxurious home with spa amenities in the middle of over 100 acres. Orchards, berries, acres of paths through stunning wildflower prairie plus a stable containing peacocks roosting in the rafters. They are 100% free range and may come visit on the deck. They even get on the roof, one bent our spire by sitting on it! Now place this private gem less than 15 minutes from Devil’s Lake and 5 min from Devil’s Head ski resort!

Family · Location · Accuracy

Park Cabin 63

The newest addition to our resort, the Park cabins offer guests a fresh stay at Sky High Camping Resort. This cabin sleeps 6 in two bedrooms with one full and two twin beds as well as a pull out couch in the living area. The Park cabin has a kitchen complete with a full fridge, a cooktop, microwave, toaster, and coffee pot as well as dishes and utensils available for your use. Additionally, this cabin has a bathroom with toilet, sink, and shower.

Value · Location · Skiing