Search Vacation Homes in Southwest Wisconsin

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Southwest Wisconsin vacation homes

Terrace/patio

The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (95 reviews)
"Great location. Has everything you need to stay."
United States
todd s.
The price is ￥20,067
￥25,721 total
includes taxes & fees
Jun 17 - Jun 18
The Bungaleau 1 Bedroom House In Cute Rivertown
Property grounds

Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (35 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is ￥14,642
￥18,836 total
includes taxes & fees
Jun 13 - Jun 14
Tamarack Point Homestead
Property grounds

Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (166 reviews)
"Beautiful house"
United States
Mario
The price is ￥22,316
￥26,932 total
includes taxes & fees
Jun 16 - Jun 17
Country home with flowing river
Outdoor dining

Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (51 reviews)
"This place was perfect for our small family. Clean, comfy beds, nice outdoor space. "
United States
Paula S.
The price is ￥21,674
￥48,929 total
includes taxes & fees
Jun 12 - Jun 13
Riverfront Twin Home
Exterior

Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (50 reviews)
"The property was beautiful and very tasteful decor. Kitchen was awsome and the rooms were comfortable and spacious. Definitely will stay here again."
United States
Shane S.
The price is ￥14,293
￥37,081 total
includes taxes & fees
Jun 18 - Jun 19
Hamilton Goebel House 816 E Louisa St Darlington Wi
Smart TV, DVD player

Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (27 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is ￥20,051
￥33,848 total
includes taxes & fees
Jun 15 - Jun 16
Hillsboro Driftless Guesthouse is cozy and ready for you!
Interior

MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (108 reviews)
"Lovely property, great location, quiet and comfortable. "
United States
T. K. D.
The price is ￥31,307
￥43,599 total
includes taxes & fees
Jun 14 - Jun 15
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Property grounds

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Northside
9.8 out of 10, Exceptional, (59 reviews)
"Was such a great place will rent from them again!! "
United States
Heather M.
The price is ￥14,633
￥26,061 total
includes taxes & fees
Jun 14 - Jun 15
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
1 bedroom, iron/ironing board, free WiFi, bed sheets

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (26 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
The price is ￥20,051
￥37,507 total
includes taxes & fees
Jun 26 - Jun 27
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Interior

The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (50 reviews)
"Excellent stay. Clean with beautiful surroundings and a great dog to greet you."
United States
Jason B.
The price is ￥25,688
￥40,651 total
includes taxes & fees
Jun 13 - Jun 14
The Honey Haven
Fridge, microwave, oven, stovetop

Ohio Street Retreat-hot tub, pool, massage chair

Ohio Street Retreat-hot tub, pool, massage chair
Prairie du Chien
10.0 out of 10, Exceptional, (83 reviews)
"Great stay overall."
United States
Keelie D.
The price is ￥22,541
￥36,820 total
includes taxes & fees
Jun 23 - Jun 24
Ohio Street Retreat-hot tub, pool, massage chair
Smart TV, fireplace

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Viola
9.0 out of 10, Wonderful, (14 reviews)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is ￥28,874
￥50,263 total
includes taxes & fees
Jun 16 - Jun 17
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
Property grounds

Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.6 out of 10, Exceptional, (60 reviews)
"Super clean, cozy, and relaxing. We enjoyed fishing and rowing around on the provided boats. We appreciated the garage filled with everything we could have possibly needed. Great price for a great trip. "
United States
Tricia H.
The price is ￥20,853
￥54,154 total
includes taxes & fees
Jun 14 - Jun 15
Lake Cottage 30 minutes from Wisconsin Dells.
Outdoor dining

Charming 3-bedroom house with WiFi, AC in serene Necedah

Charming 3-bedroom house with WiFi, AC in serene Necedah
Necedah
9.8 out of 10, Exceptional, (12 reviews)
"Love our stay! Nice cozy home with anything and everything you would need. "
United States
Susan W.
The price is ￥22,457
￥65,832 total
includes taxes & fees
Jun 22 - Jun 23
Charming 3-bedroom house with WiFi, AC in serene Necedah
Exterior

Place of Peace - the Artist's Refuge

Place of Peace - the Artist's Refuge
La Farge
9.6 out of 10, Exceptional, (18 reviews)
"Easy in and out, the house had everything we needed, and the view was amazing!"
United States
shoua x.
The price is ￥20,934
￥39,856 total
includes taxes & fees
Jun 22 - Jun 23
Place of Peace - the Artist's Refuge
Exterior

Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (13 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is ￥32,110
￥42,176 total
includes taxes & fees
Jun 14 - Jun 15
Colorful getaway in friendly Driftless village
Children's area

River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (32 reviews)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
The price is ￥32,110
￥38,450 total
includes taxes & fees
Jun 13 - Jun 14
River Road Getaway
Exterior

Budget Home. 30 Minutes from the Wisconsin Dells.

Budget Home. 30 Minutes from the Wisconsin Dells.
Adams
9.8 out of 10, Exceptional, (58 reviews)
"Have stayed here before as we play golf in the area every year. Fits our needs well."
United States
Brian B.
The price is ￥14,450
￥49,010 total
includes taxes & fees
Jun 14 - Jun 15
Budget Home. 30 Minutes from the Wisconsin Dells.
Outdoor dining

2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley

2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley
Adams
9.8 out of 10, Exceptional, (21 reviews)
"It was a beautiful house, we enjoyed our stay! Comfortably accommodated 10 people. "
United States
Stephanie G.
The price is ￥16,617
￥53,731 total
includes taxes & fees
Jun 15 - Jun 16
2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley
Exterior

Relax & Reboot in this Charming 2-Bedroom Townhome

Relax & Reboot in this Charming 2-Bedroom Townhome
Ixonia
9.8 out of 10, Exceptional, (6 reviews)
"Clean place. "
United States
John M.
The price is ￥30,799
￥42,647 total
includes taxes & fees
Jun 26 - Jun 27
Relax & Reboot in this Charming 2-Bedroom Townhome
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Wisconsin Hotel Reviews

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"best location right next to the captital, lots going on in Madison. hotel was a great value. T the bellman was very helpful in getting us acclimated"
john 2-night trip
Posted 3 hours ago
The Madison Concourse Hotel and Governor's Club

Find out more about Southwest Wisconsin

Southwest Wisconsin Vacation Homes information

Number of reviews
971
Accommodation
608 Vacation Homes
Lowest Price
￥18,836
Highest Price
￥65,832

Explore a world of travel with Expedia