Driftless Wisconsin Vacation Rentals

Compare 8 vacation rentals.
USA > Wisconsin > Driftless Wisconsin

Make Driftless Wisconsin your next getaway

Discover the hidden gem of Driftless Wisconsin, where rolling hills, meandering rivers, and charming small towns await your exploration. This unique region, untouched by glaciers during the last Ice Age, offers a landscape unlike any other in the state, with stunning bluffs, deep valleys, and limestone caves to captivate visitors.

Explore Driftless Wisconsin house rentals, cottages, and more

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House rentals

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Cottages

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Popular amenities for Driftless Wisconsin vacation rentals

Popular
Dog-friendly Hot tub Internet
Crystal Moon Retreat
3 Bedroom | 3 Bath | Sleeps 6

Crystal Moon Retreat - Eastman, WI

$339 avg / night
5.0 (7)
Balsam House
4 Bedroom | 2 Bath | Sleeps 8

Balsam House - Baraboo, WI

$357 avg / night
4.33 (15)
Wills Lane
4 Bedroom | 1.5 Bath | Sleeps 9

Wills Lane - Darlington, WI

$264 avg / night
4.78 (9)
Baraboo Grove
4 Bedroom | 3 Bath | Sleeps 10

Baraboo Grove - Baraboo, WI

$297 avg / night
4.17 (6)
Happy Landings @ Dells Doorstep
2 Bedroom | 1 Bath | Sleeps 6

Happy Landings @ Dells Doorstep - Baraboo, WI

$191 avg / night
4.57 (7)

View 3 more homes

Recent Driftless Wisconsin guest reviews

We spent our winter family vacation at Balsam House this year. There were 4 adults, a toddler, an infant and my daughters dog. The home was cute and comfy and had enough space for all of us to relax and spend time together. We were able to walk to the downtown area which was picture perfect with great coffee shops and restaurants. There was also a small zoo nearby that my 2 year old grandson really enjoyed. We ate mostly take-out but we also were able to cook a dinner at the house using the cookware and utensils provided. Activities included skiing at Chestnut Mountain and visiting a children’s museum for an afternoon of fun. All the adults enjoyed the hot tub at some point. The home is at the top of a hill and the back yard felt private while offering a nice view across the town. I appreciated the EV charger to top off my car before heading home. We would definitely stay here again.
Adele P. | Jan 2025
This house was very clean and had everything we needed. The hot tube was great.
Steve T. | Dec 2024
The house was perfect. It was well stocked with everything we needed for our 1 week stay. It was clear that the owners put a lot of thought into what their guests might want and need. The kitchen was stocked with pots and pans, seasonings, coffee making supplies (filters, sugar, ect), and even a crock pot. The beds were very comfortable. The property was very pretty and clean. I would highly recommend this rental to anyone looking for a country get away.
Traci L. | Nov 2024
Driftless Wisconsin vacation rental FAQ

Yes. 7 of our Driftless Wisconsin vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Driftless Wisconsin vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Driftless Wisconsin team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Driftless Wisconsin, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
Vacasa Guest Value Prop Icon check-in
Seamless check-in
Vacasa Guest Value Prop Icons cleaning
Professional cleaning

Where is Driftless Wisconsin?

Nestled in the southwestern part of Wisconsin, Driftless Wisconsin encompasses towns such as Viroqua, Spring Green, and Mineral Point. Surrounded by the Mississippi River to the west and the Wisconsin River to the south, this area is a haven for outdoor enthusiasts, artists, and those seeking a peaceful retreat. With its proximity to Madison and La Crosse, Driftless Wisconsin offers a perfect balance of seclusion and accessibility.

Things to do on a Driftless Wisconsin vacation

Driftless Wisconsin beckons travelers with a plethora of activities year-round. Explore the region's renowned vineyards and wineries, take a scenic drive along the Great River Road, or hike through picturesque state parks like Wyalusing and Governor Dodge. Visit Taliesin, Frank Lloyd Wright's architectural masterpiece, or indulge in the local arts scene with galleries and studios scattered throughout the area. Whether you're into birdwatching, fishing, antiquing, or simply relaxing in nature, Driftless Wisconsin has something for everyone.

Immerse yourself in the beauty and tranquility of Driftless Wisconsin with a stay in one of our charming vacation rentals. Whether you're seeking a romantic getaway, a family adventure, or a solo retreat, Driftless Wisconsin promises an unforgettable experience amidst its scenic splendor.