What are the top rated Cottage Rentals in Southern Wisconsin?

There are a lot of options in Southern Wisconsin. If you plan on staying in the Southern Wisconsin area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Southern Wisconsin: <a href="/property/seagull-beach-guest-house-unique-lake-michigan-cottagenon-private-beach/HA-1214864182" class="class="static-page-link"">Seagull Beach Guest House, Unique Lake Michigan Cottagenon private beach</a> <a href="/property/clarance-gonstead-guest-cottage-prairie-style-stone-tide-water-cypress/HA-321139397" class="class="static-page-link"">Clarance Gonstead Guest Cottage, Prairie Style, Stone &amp; Tide Water Cypress</a> <a href="/property/lake-michigan-sand-beach-wooded-privacy/HA-32139493" class="class="static-page-link"">Lake Michigan Sand Beach &amp; Wooded Privacy</a> <a href="/property/winter-dates-available-at-beachdaze/HA-3212016502" class="class="static-page-link"">Winter dates available at Beachdaze!</a> <a href="/property/romantic-bed-and-breakfast-cottage/HA-1213734652" class="class="static-page-link"">Romantic Bed And Breakfast Cottage.</a> <a href="/property/unique-a-renovated-old-railroad-depot-turned-into-a-cozy-cottage/HA-1214547231" class="class="static-page-link"">Unique! A renovated old railroad depot turned into a cozy cottage.</a> <a href="/property/lakeside-cottage-with-pier-great-for-family-swimming-fishing-close-to-dell-s/HA-1214131803" class="class="static-page-link"">Lakeside Cottage With Pier, Great For Family, Swimming, Fishing, Close To Dell&#39;s</a> <a href="/property/wonderful-sunsets/HA-3212334412" class="class="static-page-link"">Wonderful Sunsets</a> <a href="/property/family-friendly-lake-home-sleeps-14-sandy-beach-lake-toys-fire-pit-sunrises/HA-3214292778" class="class="static-page-link"">Family Friendly Lake Home Sleeps 14, Sandy Beach, Lake Toys, Fire Pit, Sunrises!</a> <a href="/property/private-beach-outdoor-dining-firepit/HA-321907412" class="class="static-page-link"">Private Beach, Outdoor Dining, Firepit</a>

How much does it cost to rent a cottage in Southern Wisconsin?

The average cost for a cottage rental in Southern Wisconsin is $306 per night. Madisonvacationrental has a wide list of great cottages near Southern Wisconsin that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Southern Wisconsin that allow pets?

Yes, here are the top cottage rentals in Southern Wisconsin that allow you to bring your pet: Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops Airy Cottage with Dock and Views on Buffalo Lake! Large Home w/Indoor Basketball Court + Game Room! Island View Hideaway- Hot Tub, Nearby Skiing, Peaceful, Scenic, Birds, Nature! <a href="/all/usa/wisconsin/southern-wisconsin" class="class="static-page-link"">See all pet-friendly vacation rentals in Southern Wisconsin on Madisonvacationrental</a>

Do you have any rental cottages in Southern Wisconsin that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Southern Wisconsin to find one that works for you.

Are there quality cottages in Southern Wisconsin that have indoor swimming pools?

As of 2026, the data from Madisonvacationrental shows that there are Over 508 private swimming pools or cottages with indoor pools in the Southern Wisconsin area along with other great amenities.

Southern Wisconsin Cottage Rentals By Owner

Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

From US $139

10.0 (241 Reviews)

Cottage

Coulee Region beauty-"coulee" to describe valleys that dissect verdant ridgetops

Air Conditioner
Parking
TV

Southern Wisconsin Cottage Rentals & Holiday Homes

Find the best cottages in Southern Wisconsin - We found 508 exact matches

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