Southwest Wisconsin Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Southwest Wisconsin vacation rentals
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Wild Rose, Outdoor Collection by Marriott BonvoyWild Rose
9.8 out of 10, Exceptional, (44)
"The staff was great and i enjoyed the entire stay."
Wakeem
The price is ￥15,456
￥23,762 total
includes taxes & fees
Jan 7 - Jan 8, 2026
9.8 out of 10, Exceptional, (6)
"This is a great place to stay -- very clean and new and well equipped in the kitchen. Very close to golf --- easy access to get in the place and the owner was very accomodating"
David
The price is ￥51,565
￥58,526 total
includes taxes & fees
Dec 25 - Dec 26
9.4 out of 10, Exceptional, (122)
"Great stay at the Dylin"
Lauri
The price is ￥16,856
￥19,468 total
includes taxes & fees
Dec 29 - Dec 30
10.0 out of 10, Exceptional, (1)
"We had a wonderful time and would defiinitely stay again. "
Julie
The price is ￥32,173
￥35,913 total
includes taxes & fees
Dec 29 - Dec 30
8.0 out of 10, Very Good, (1)
"There was a terrible smell in the house. Smelled smoky, even though there were "No Smoking" signs posted in several places. I bought a neutralizing spray and used it every time we entered and exited. It helped a little. Beds were comfortable. We were cold the first night because I didn't know right away how to adjust the thermostat. Shower was new and nice. We arrived in the dark and there was a couple of "scary" people on the front steps. It felt safer in the daylight. "
terri
The price is ￥13,426
￥32,541 total
includes taxes & fees
Dec 27 - Dec 28
10.0 out of 10, Exceptional, (4)
"It was very roomy and easily accessible. The views were amazing. Would recommend to anyone anytime!!"
Greg
9.2 out of 10, Wonderful, (39)
"Place was clean and comfortable. "
Tristan
The price is ￥19,296
￥20,358 total
includes taxes & fees
Dec 31 - Jan 1, 2026
9.2 out of 10, Wonderful, (1220)
"Enjoyed our stay, perfect location !"
Lisa
The price is ￥24,433
￥27,732 total
includes taxes & fees
Dec 25 - Dec 26
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find vacation rentals that suit your style
Cottages
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Southwest Wisconsin Hotel Reviews
Baymont by Wyndham Madison West/Middleton WI West
10/10 Excellent
Find out more about Southwest Wisconsin
Search for holiday rentals in Southwest Wisconsin on Expedia! You can easily find your home rentals, villas, holiday apartments in Southwest Wisconsin using one of the methods below:
- View our selection of featured holiday rentals in Southwest Wisconsin
- Use the map to find apartments and other holiday homes in the Southwest Wisconsin neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Southwest Wisconsin while they last
Look no further and take a look at our great range of rental properties in Southwest Wisconsin!
Explore a world of travel with Expedia
- Vacation Homes in Southwest Wisconsin
- Condo Rentals in Southwest Wisconsin
- Apartments in Southwest Wisconsin
- Cabin Rentals in Southwest Wisconsin
- Resorts in Southwest Wisconsin
- Cottages in Southwest Wisconsin
- Motels in Southwest Wisconsin
- B&B in Southwest Wisconsin
- Lodges in Southwest Wisconsin
- Farmstay in Southwest Wisconsin
- Chalets in Southwest Wisconsin
- Villas in Southwest Wisconsin
- RV Parks in Southwest Wisconsin
- Guest Houses in Southwest Wisconsin
- Aparthotels in Southwest Wisconsin
- Holiday Park Resorts in Southwest Wisconsin
- Hostels in Southwest Wisconsin
- Castles in Southwest Wisconsin
