Search Vacation Homes in Southwest Wisconsin

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Southwest Wisconsin vacation homes

Property grounds
Tamarack Point Homestead

Vacation Home in Arcadia

Tamarack Point Homestead
10.0 out of 10, Exceptional, (32)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
United States
Luke H.
The price is ￥14,210
￥18,280 total
includes taxes & fees
Dec 15 - Dec 16
Tamarack Point Homestead
Exterior
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Vacation Home in Mount Horeb

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
The price is ￥17,139
￥30,130 total
includes taxes & fees
Dec 28 - Dec 29
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Fridge, microwave, oven, stovetop
Hamilton Goebel House 816 E Louisa St Darlington Wi

Vacation Home in Darlington

Hamilton Goebel House 816 E Louisa St Darlington Wi
9.8 out of 10, Exceptional, (48)
"Close to town. "
United States
Juanita W.
The price is ￥15,425
￥37,365 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Hamilton Goebel House 816 E Louisa St Darlington Wi
Terrace/patio
Ohio Street Retreat-hot tub, massage chair, pool

Vacation Home in Prairie du Chien

Ohio Street Retreat-hot tub, massage chair, pool
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."
United States
Kristine C.
The price is ￥17,669
￥30,081 total
includes taxes & fees
Dec 22 - Dec 23
Ohio Street Retreat-hot tub, massage chair, pool
Property grounds
French Island w/Hot Tub, Kayak, Lake View, EV

Vacation Home in La Crosse

French Island w/Hot Tub, Kayak, Lake View, EV
10.0 out of 10, Exceptional, (19)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is ￥20,255
￥47,235 total
includes taxes & fees
Dec 16 - Dec 17
French Island w/Hot Tub, Kayak, Lake View, EV
TV, fireplace
Cozy and charming cabin! Perfect for getaways and fun activities for all ages

Vacation Home in Baraboo

Cozy and charming cabin! Perfect for getaways and fun activities for all ages
9.0 out of 10, Wonderful, (25)
"Not a bad place for a short stay"
United States
India H.
The price is ￥22,904
￥51,994 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy and charming cabin! Perfect for getaways and fun activities for all ages
Game room
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola

Vacation Home in Viola

Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
9.6 out of 10, Exceptional, (7)
"Beautiful place. We loved the access to the river. "
United States
dwaterman21
The price is ￥28,046
￥48,822 total
includes taxes & fees
Dec 15 - Dec 16
Blakley Hobbit Charming 2-bedroom country house with AC, WiFi in soothing Viola
TV, fireplace
Riverfront Twin Home

Vacation Home in La Crosse

Riverfront Twin Home
10.0 out of 10, Exceptional, (43)
"Great place to stay! Had everything we needed!"
United States
Angie C.
The price is ￥21,034
￥48,023 total
includes taxes & fees
Dec 15 - Dec 16
Riverfront Twin Home
Outdoor dining
Serenity Cottage at Mineral Point

Vacation Home in Mineral Point

Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (103)
"Outstanding property, great location, will stay again."
United States
James S.
The price is ￥24,540
￥35,727 total
includes taxes & fees
Dec 15 - Dec 16
Serenity Cottage at Mineral Point
Interior
The Honey Haven

Vacation Home in Westby

The Honey Haven
10.0 out of 10, Exceptional, (46)
"Everything was great, from check in to check out. Hosts answered questions almost immediately and were very friendly and helpful. "
United States
Mary B.
The price is ￥23,372
￥37,479 total
includes taxes & fees
Dec 15 - Dec 16
The Honey Haven
Smart TV, fireplace, books
Winter Romance • Hot Tub + Cozy Fireplace

Vacation Home in Wautoma

Winter Romance • Hot Tub + Cozy Fireplace
9.8 out of 10, Exceptional, (34)
"This is a Great Lake house spot to stay if you want to get away."
United States
Brian W.
The price is ￥20,612
￥64,030 total
includes taxes & fees
Dec 15 - Dec 16
Winter Romance • Hot Tub + Cozy Fireplace
Private kitchen
Jake's Place

Vacation Home in Powell-Poage-Hamilton

Jake's Place
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is ￥19,476
￥46,051 total
includes taxes & fees
Dec 15 - Dec 16
Jake's Place
Fridge, microwave, oven, stovetop
Hot Tub - King Suite - Game Room - Large Groups

Vacation Home in Sun Prairie

Hot Tub - King Suite - Game Room - Large Groups
10.0 out of 10, Exceptional, (15)
"We had a great visit "
United States
Jennifer D.
The price is ￥31,162
￥99,253 total
includes taxes & fees
Dec 17 - Dec 18
Hot Tub - King Suite - Game Room - Large Groups
Fridge, microwave, oven, stovetop
Fawn Lake Cottage for Families Looking for Privacy

Vacation Home in Wisconsin Dells

Fawn Lake Cottage for Families Looking for Privacy
2.0 star property
9.6 out of 10, Exceptional, (7)
"Everything was smooth and super close to the dells, very nice place!"
United States
Cody M.
The price is ￥16,672
￥48,618 total
includes taxes & fees
Dec 15 - Dec 16
Fawn Lake Cottage for Families Looking for Privacy
Fridge, microwave, oven, stovetop
Hillsboro Driftless Guesthouse is cozy and ready for you!

Vacation Home in Hillsboro

Hillsboro Driftless Guesthouse is cozy and ready for you!
10.0 out of 10, Exceptional, (25)
"Stayed for a weeding at the brewery in town and this place was perfect. Had young kids that loved the big yard and park down the street. "
United States
Matt B.
The price is ￥17,529
￥28,521 total
includes taxes & fees
Dec 15 - Dec 16
Hillsboro Driftless Guesthouse is cozy and ready for you!
Fridge, microwave, oven, stovetop
Great 1 Bedroom unit with easy access to everything

Vacation Home in Lower Northside

Great 1 Bedroom unit with easy access to everything
9.6 out of 10, Exceptional, (53)
"Great location, close to downtown, mall, river etc. very clean. Close to good coffee and restaurants. Great place"
United States
Dan M.
The price is ￥17,918
￥35,839 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Great 1 Bedroom unit with easy access to everything
Property grounds
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Vacation Home in Northside

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
9.8 out of 10, Exceptional, (46)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
The price is ￥13,742
￥23,867 total
includes taxes & fees
Dec 18 - Dec 19
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Property grounds
Arcade/Fireplace/CoffeeBar The Holidays Start Here

Vacation Home in Milton

Arcade/Fireplace/CoffeeBar The Holidays Start Here
10.0 out of 10, Exceptional, (17)
"We had the best VRBO experience at Harbor House. The hosts are absolutely fabulous. The house was perfect, just as presented online. 6 of us adults and a little French bulldog spent a long weekend there so we could cheer on our son (one of the visitors) as he ran the half Ironman in Madison. He LOVED the hot tub afterward. Great visit. Would definitely stay again if in the area."
United States
Karrie S.
Arcade/Fireplace/CoffeeBar The Holidays Start Here
Outdoor dining
River Road Getaway

Vacation Home in Muscoda

River Road Getaway
9.6 out of 10, Exceptional, (29)
"Nice clean place to stay for weekend vacation:) would stay again if in the area"
United States
Anonymous traveler
The price is ￥31,162
￥37,150 total
includes taxes & fees
Dec 15 - Dec 16
River Road Getaway
Terrace/patio
Place of Peace - the Artist's Refuge

Vacation Home in La Farge

Place of Peace - the Artist's Refuge
9.8 out of 10, Exceptional, (17)
"It was great! The place is calm and quiet and surrounded by beautiful nature. Best place to decompress before classes start."
United States
Claudia S.
The price is ￥20,333
￥38,384 total
includes taxes & fees
Dec 20 - Dec 21
Place of Peace - the Artist's Refuge
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

Hampton Inn & Suites Madison / Downtown

Hampton Inn & Suites Madison / Downtown

10/10 Excellent
"Clean room, friendly staff"
Lori 2-night trip
Posted 1 day ago
Hampton Inn & Suites Madison / Downtown

Find out more about Southwest Wisconsin

Southwest Wisconsin Vacation Homes information

Number of reviews
655
Accommodation
532 Vacation Homes
Lowest Price
￥18,280
Highest Price
￥99,253

Explore a world of travel with Expedia