Southwest Wisconsin Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Southwest Wisconsin

Exterior
Tiny House on the River

Tiny House on the River

Black River Falls
10.0 out of 10, Exceptional, (80)
"The house was beautiful, the fishing was great. It was a wonderful place to relax and reset."
United States
Crystal K.
$203 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Tiny House on the River
Smart TV
RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife

Princeton
10.0 out of 10, Exceptional, (40)
"We loved this quiet getaway! Simply perfect and simple. Great sunsets and rainbows! "
United States
Kevin
$209 nightly
The price is $220
Dec 9 - Dec 10
Total with taxes and fees
RiverFront Cottage>Private Pier>Firepit & Wildlife
Outdoor spa tub
Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Eastman
9.8 out of 10, Exceptional, (7)
"This is the perfect spot for two! The view from the deck is absolutely beautiful. The hot tub was a bonus. We would definitely stay again. "
United States
Colleen
$243 nightly
The price is $256
Dec 7 - Dec 8
Total with taxes and fees
Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Exterior
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
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
$169 nightly
The price is $187
Dec 6 - Dec 7
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Interior entrance
The Dylin by Mint House

The Dylin by Mint House

4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (118)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
$112 nightly
The price is $129
Dec 22 - Dec 23
Total with taxes and fees
The Dylin by Mint House
Fridge, microwave, oven, stovetop
Cozy first floor at the heart of downtown Viroqua

Cozy first floor at the heart of downtown Viroqua

Viroqua
10.0 out of 10, Exceptional, (52)
"Great convenience, quiet, well maintained, cute & cozy! Would definitely stay again! "
United States
Lynette W.
$160 nightly
The price is $178
Dec 6 - Dec 7
Total with taxes and fees
Cozy first floor at the heart of downtown Viroqua
Property grounds
Tamarack Point Homestead

Tamarack Point Homestead

Arcadia
10.0 out of 10, Exceptional, (31)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
United States
Luke H.
$111 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Tamarack Point Homestead
Fridge, microwave, coffee/tea maker, toaster
Quaint cabin overlooking the creek below and wetlands in the valley basin.

Quaint cabin overlooking the creek below and wetlands in the valley basin.

Norwalk
10.0 out of 10, Exceptional, (19)
"Perfect little place for a getaway. Clean, comfortable and nice amenities for a cabin in the woods. Beautiful setting, and still within driving distance of restaurants and other recreational activities."
United States
Nathan U.
$187 nightly
The price is $197
Dec 8 - Dec 9
Total with taxes and fees
Quaint cabin overlooking the creek below and wetlands in the valley basin.
Dining
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Lyndon Station
10.0 out of 10, Exceptional, (60)
"A fantastic little getaway. Well appointed with things to do and close to things to see. Very peaceful setting."
United States
Alexander H.
$265 nightly
The price is $280
Dec 7 - Dec 8
Total with taxes and fees
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
TV
A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney

Mineral Point
9.6 out of 10, Exceptional, (118)
"Comfortable, easy stay for a weekend. "
United States
Kelly
$189 nightly
The price is $209
Dec 7 - Dec 8
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Interior
River Road Retreat

River Road Retreat

Muscoda
9.6 out of 10, Exceptional, (23)
"Loved the place. Very clean & cozy. We go back to stay "
United States
Christy G.
$226 nightly
The price is $238
Dec 6 - Dec 7
Total with taxes and fees
River Road Retreat
Interior
Spacious Condo: Historic Boutique Rental in Downtown Edgerton

Spacious Condo: Historic Boutique Rental in Downtown Edgerton

2.0 star property
Edgerton
10.0 out of 10, Exceptional, (5)
"The feel was exactly what we were looking for! Great and very helpful staff!! Highly recommend and will more than likely stay again!!"
United States
Jeff M.
$246 nightly
The price is $254
Dec 7 - Dec 8
Total with taxes and fees
Spacious Condo: Historic Boutique Rental in Downtown Edgerton
Exterior
Quiet And Beautiful!!

Quiet And Beautiful!!

Warrens
9.2 out of 10, Wonderful, (190)
"Great place to stay plenty of room and very quiet. "
United States
Matthew
$314 nightly
The price is $331
Dec 13 - Dec 14
Total with taxes and fees
Quiet And Beautiful!!
Fridge, microwave, oven, stovetop
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, (48)
"Close to town. "
United States
Juanita W.
$219 nightly
The price is $240
Dec 31 - Jan 1, 2026
Total with taxes and fees
Hamilton Goebel House 816 E Louisa St Darlington Wi
2 bedrooms, iron/ironing board, WiFi, bed sheets
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

Richland Center
10.0 out of 10, Exceptional, (31)
"Wonderful, clean, quiet."
United States
Radka R.
$172 nightly
The price is $181
Dec 6 - Dec 7
Total with taxes and fees
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center
Outdoor dining
Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point

Mineral Point
10.0 out of 10, Exceptional, (101)
"Outstanding property, great location, will stay again."
United States
James S.
$209 nightly
The price is $230
Dec 9 - Dec 10
Total with taxes and fees
Serenity Cottage at Mineral Point
Property grounds
Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”

Edgerton
9.2 out of 10, Wonderful, (47)
"Checkin was super easy, great amenities, and cozy cabin atmosphere."
United States
Nicholas R.
$154 nightly
The price is $162
Dec 7 - Dec 8
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”
Fridge, microwave, oven, stovetop
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Wisconsin Dells
10.0 out of 10, Exceptional, (9)
"Excellent location, quiet, and very clean. Would stay again "
United States
Allen B.
$332 nightly
The price is $367
Dec 7 - Dec 8
Total with taxes and fees
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
TV, fireplace
Riverfront Twin Home

Riverfront Twin Home

La Crosse
10.0 out of 10, Exceptional, (42)
"Great place to stay! Had everything we needed!"
United States
Angie C.
$265 nightly
The price is $305
Dec 7 - Dec 8
Total with taxes and fees
Riverfront Twin Home
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.
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Top Southwest Wisconsin Hotel Reviews

DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

10/10 Excellent
"Excellent, the front desk was amazing."
Sultanand Rashid 1-night trip
Posted 21 hours ago
DoubleTree by Hilton Madison East

Find out more about Southwest Wisconsin

Everything you need to know about Southwest Wisconsin vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Wisconsin vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Wisconsin vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Wisconsin vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Wisconsin. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southwest Wisconsin in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southwest Wisconsin rentals

At Expedia, we put the best Southwest Wisconsin vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southwest Wisconsin rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Wisconsin vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Wisconsin. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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