Holiday rentals in Cascade Mountain

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Top-rated holiday rentals in Cascade Mountain

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Guest favourite
Aerial view of a house nestled among dense green trees, showcasing a red roof that contrasts with the surrounding foliage. The property is partially visible, with a patio area indicated by an outdoor table and chairs situated near the home.
Home in Portage
4.94 out of 5 average rating, 89 reviews

*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!

Top guest favourite
The contemporary kitchen features a large central island with a rustic wood countertop and ample seating. Expansive windows offer scenic views of the surrounding nature, while modern appliances and cabinetry provide functionality. The open layout promotes a spacious feel, complemented by polished concrete flooring.
Cottage in Portage
5 out of 5 average rating, 17 reviews

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.

Top guest favourite
The dome structure glimmers in the moonlight, surrounded by tall trees that create a serene ambiance. A warm glow from a nearby fire pit reflects off the dome's surface, enhancing its unique design. The wooden platform adds a cozy touch to the natural setting.
Dome in Wisconsin Dells
4.97 out of 5 average rating, 182 reviews

Dells Domes - Riverview Escape - Glamping Dome 4

Staying in a dome amidst nature is a unique experience. The circular structure offers an amazing view of the surroundings, with peaceful sounds of rustling leaves, chirping birds, and a flowing river below. The cozy dome has a queen size bed, night stands, a seating area, mini fridge, and a k-cup coffee maker & heater/ac. At night, the starry sky and nature's sounds lull you to sleep. Waking up, you feel refreshed, and the peaceful surroundings and breathtaking views leave a lasting impression.

Guest favourite
Flat in Portage
4.9 out of 5 average rating, 180 reviews

Comfy Nook, 20 Minutes From Wisconsin Dells

This apartment has two bedrooms and one bath. Located in downtown Portage, just 20 minutes from Wisconsin Dells easy access to the interstate. Cascade mountain just a few minutes away. There is a driveway for off-street parking for two cars. There is a private outside stairwell entrance and keypad door lock for access. This apartment is older construction and is on the 2nd floor. The floors are squeaky and noise will carry to the lower unit. Quiet time at 10:00pm. Just a short walk to downtown.

Top guest favourite
Home in Baraboo
5 out of 5 average rating, 49 reviews

Tree House Lodge, Baraboo Bluffs

Not just a place to stay but an experience! One of a kind, stunningly beautiful, peaceful retreat on a dead end road in the Baraboo Bluffs. Feel one with nature with more windows than walls. Listen to the owls talk to one another and see deer and turkey pass through daily. Numerous critters to see and hear whether sitting inside or out. Just minutes from Devils Lake, Devils Head, Durwards Glen, ice age trails, winery's and only 25 min from the Dells but you probably won't want to go anywhere!

Top guest favourite
The open living area features high ceilings and large windows that allow natural light to fill the space. A green sectional sofa and matching ottoman are arranged around a coffee table. A wooden dining table is visible in the background, along with a modern kitchen.
Cabin in Portage
4.95 out of 5 average rating, 127 reviews

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.

Guest favourite
A spacious outdoor deck is furnished with a table, six chairs, and a fire table, all set beneath a large umbrella. Lush green trees surround the area, providing a private, serene atmosphere for relaxation and gatherings.
Home in Portage
4.93 out of 5 average rating, 40 reviews

Summer Woods Retreat Near WI Dells & Devil’s Lake

Summer 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.

Top guest favourite
An open-concept living space is captured, featuring a modern kitchen, a dining table, and a stone fireplace. The cozy seating area invites togetherness. An inviting hot tub sits on a covered deck, surrounded by trees. A sauna made of warm wood offers an additional relaxation option.
Cabin in Baraboo
4.98 out of 5 average rating, 112 reviews

Sauna | Hot Tub | EV+ | Luxury | Cozy | Private

Nestled in the country, this luxurious home offers a serene escape from the hustle of city life. Enjoy two spacious bedrooms and two meticulously designed bathrooms featuring indulgent amenities, such as a deep soaking tub. A cozy living area with a stone fireplace invites relaxation, while a gourmet kitchen beckons culinary adventures. Outside, soak in the hot tub, grill up some dinner, share stories around the fire, or watch the sunset from the sauna, all amidst nature's embrace.

Top guest favourite
A spacious living area is highlighted by large glass doors that open to the outdoors, allowing natural light to fill the room. A plush green sofa complements mid-century chairs and a round coffee table. A patterned rug adds warmth beneath, while a modern ceiling fan circulates air.
Cottage in Portage
5 out of 5 average rating, 86 reviews

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.

Guest favourite
Cabin in Merrimac
4.92 out of 5 average rating, 273 reviews

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!

Top guest favourite
Home in Portage
5 out of 5 average rating, 62 reviews

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!

Top guest favourite
Home in Merrimac
5 out of 5 average rating, 69 reviews

Summertime in the driftless region

Cozy home in the heart of the Baraboo Bluff area, just minutes away from the iconic Devil's Lake State Park, Parfrey's Glen, Lake Wisconsin, and other popular attractions like Devil's Head, Cascade Mountain, and the Wisconsin Dells. The area offers tranquility and seasonal adventure including hiking, golf, boating, swimming, and skiing. As well as great restaurants, and charming boutiques. The area offers fun for all ages no matter the weather.

Popular amenities for Cascade Mountain holiday rentals