Driftless Wisconsin Vacation Rentals

Compare 6 vacation rentals.
1 Guest
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

$352 avg / night
(excludes fees and taxes)
5.0 (11)
Wills Lane
4 Bedroom | 1.5 Bath | Sleeps 9

Wills Lane - Darlington, WI

$297 avg / night
(excludes fees and taxes)
4.85 (13)
Balsam House
4 Bedroom | 2 Bath | Sleeps 8

Balsam House - Baraboo, WI

$384 avg / night
(excludes fees and taxes)
4.38 (16)
Happy Landings at Dells Doorstep
2 Bedroom | 1 Bath | Sleeps 6

Happy Landings at Dells Doorstep - Baraboo, WI

$184 avg / night
(excludes fees and taxes)
4.57 (7)
Lake Wisconsin, Sunset Bay
4 Bedroom | 3 Bath | Sleeps 12

Lake Wisconsin, Sunset Bay - Lodi, WI

$476 avg / night
(excludes fees and taxes)

View 1 more homes

Recent Driftless Wisconsin guest reviews

Loved the hot tub, had all amenities we could have wanted & extra back up supplies in case we forgot anything. Loved the hammock & outdoor seating options, and the campfire! We a perfect weekend getaway :)
Elizabeth B. | Jun 2025
Very beautiful home, extremely well thought out and loved it!
john w. | May 2025
Met all our expectations. The only thing I would say, there are no outlets in the bedrooms but a power strip and drop cord took care of that issue. Beautiful setting in the country, and the cows and calves were fun to watch.
Terry B. | Apr 2025
Driftless Wisconsin vacation rental FAQ

Yes. 5 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 the 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 problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Driftless Wisconsin, log in to Trip Manager to explore the 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.
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