Search Vacation Homes in Southwest Wisconsin
Bundle & SaveGet more, spend less whenever you see Bundle & Save deals
OneKeyCashEarn OneKeyCash on all your eligible bookings
Upfront pricingWe are not like the others - we include taxes and fees
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Southwest Wisconsin vacation homes
Tamarack Point Homestead
Tamarack Point HomesteadArcadia
10.0 out of 10, Exceptional, (32)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
Luke H.
$111 nightly
The price is $117
Dec 22 - Dec 23
Total with taxes and fees
Beautiful House! 15min away from Wisconsin Dells, Skiing Resorts and Devils lake
Beautiful House! 15min away from Wisconsin Dells, Skiing Resorts and Devils lakeBaraboo
9.4 out of 10, Exceptional, (3)
"A nice place in Baraboo WI for a weekend getaway close to ski areas "
Cecilia L.
$286 nightly
The price is $325
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
Hamilton Goebel House 816 E Louisa St Darlington WiDarlington
9.8 out of 10, Exceptional, (48)
"Close to town. "
Juanita W.
$208 nightly
The price is $228
Dec 31 - Jan 1, 2026
Total with taxes and fees
Serenity Cottage at Mineral Point
Serenity Cottage at Mineral PointMineral Point
10.0 out of 10, Exceptional, (103)
"Outstanding property, great location, will stay again."
James S.
$191 nightly
The price is $211
Dec 29 - Dec 30
Total with taxes and fees
Jake's Place
Jake's PlacePowell-Poage-Hamilton
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
Cori C.
$285 nightly
The price is $328
Jan 4 - Jan 5, 2026
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing ComfortMount Horeb
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
Holly
$175 nightly
The price is $193
Dec 28 - Dec 29
Total with taxes and fees
Ohio Street Retreat-hot tub, massage chair, pool
Ohio Street Retreat-hot tub, massage chair, poolPrairie du Chien
10.0 out of 10, Exceptional, (71)
"We had a wonderful weekend enjoying all the parks the area has to offer. The pool and massage chair were a nice added perk to the property, especially after hiking in the parks."
Kristine C.
$197 nightly
The price is $207
Jan 11 - Jan 12, 2026
Total with taxes and fees
The Honey Haven
The Honey HavenWestby
10.0 out of 10, Exceptional, (46)
"Wonderful! Beautiful, serene place, clean environment, perfect!"
Karen S.
$229 nightly
The price is $242
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
Cabins
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Southwest Wisconsin Hotel Reviews
The Madison Concourse Hotel and Governor's Club
10/10 Excellent
Find out more about Southwest Wisconsin
Southwest Wisconsin Vacation Homes information
Number of reviews | 725 |
|---|---|
Accommodation | 532 Vacation Homes |
Lowest Price | $117 |
Highest Price | $427 |
Explore a world of travel with Expedia
- Cabin Rentals in Richland Center
- Motels in Richland Center
- Apartments in Richland Center
- RV Parks in Richland Center
- Condo Rentals in Richland Center
- Richland Center Hotels
- Hotels near A.D. German Warehouse
- Historic Hotels in Richland Center
- Hotels with an Indoor Pool in Richland Center
- Pet-friendly Hotels in Richland Center
- Hotels with a Gym in Richland Center
- 4 Star Hotels in Richland Center
- Hotels with Bars in Richland Center
- Americinn Hotels in Richland Center
- 5 Star Hotels in Richland Center
- Cheap Hotels in Richland Center
- Family Hotels in Richland Center
- Hotels with a Pool in Richland Center
- Hotels with Hot Tubs in Richland Center
- Hill Point Hotels
- Yuba Hotels
- Cabin Rentals in Gotham
- Apartments in Gotham
- Motels in Gotham
- Gotham Hotels
- Ironton Hotels
- Motels in West Lima
- Cabin Rentals in West Lima
- Hotels near 400 State Trail
- Cabin Rentals in Avoca
- Vacation Homes in Avoca
- Cottages in Avoca
- Apartments in Avoca
- West Lima Hotels
- Avoca Hotels
- 5 Star Hotels in Avoca
- Cabin Rentals in La Valle
- RV Parks in La Valle
- B&B in La Valle
- Cottages in La Valle
- Motels in La Valle
- Hotels near Eagle Cave
- Cabin Rentals in Muscoda
- Motels in Muscoda
- Cabin Rentals in Plain
- La Valle Hotels
- 4 Star Hotels in La Valle
- Muscoda Hotels
- Lone Rock Hotels
- 3 Star Hotels in Plain
- Plain Hotels
- 5 Star Hotels in Plain
- Cabin Rentals in Hillsboro
- Vacation Homes in Hillsboro
- B&B in Hillsboro
- Ranches in Hillsboro
- Flights to Richland Center
- Flights from New York to Richland Center
- Flights from Chicago to Richland Center
- Flights from Houston to Richland Center
- Flights from Phoenix to Richland Center
- Flights from Hill Point
- Flights to Gotham
- Flights from Gotham
- Flights to La Valle
- Flights to Muscoda
- Flights to Plain
- Car rentals near Hub City
- Car rentals near Richland Center
- Enterprise Rental Cars in Richland Center
- Avis Rental Cars in Richland Center
- Van Car Rentals in Richland Center
- Budget Rental Cars in Richland Center
- Dollar Rent A Car Rental Cars in Richland Center
- Car rentals near Lime Ridge
- Car rentals near Cazenovia
- Car rentals near Boaz
- Car rentals near Gotham
- Car rentals near Basswood
- Car rentals near Ironton
- Car rentals near Loganville
- Car rentals near Avoca
- Car rentals near La Valle
- Car rentals near Muscoda
- Car rentals near Lone Rock
- Car rentals near Plain