Search Cottages in Southwest Wisconsin

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Southwest Wisconsin cottages

Exterior
Tiny House on the River

Tiny House on the River

Tiny House on the River
Black River Falls
10.0 out of 10, Exceptional, (81)
"The house was beautiful, the fishing was great. It was a wonderful place to relax and reset."
United States
Crystal K.
The price is HK$1,049
HK$1,775 total
includes taxes & fees
5 Jan - 6 Jan 2026
Tiny House on the River
Property grounds
Lakefront Couples Retreat | Hot Tub & Fireplace

Lakefront Couples Retreat | Hot Tub & Fireplace

Lakefront Couples Retreat | Hot Tub & Fireplace
Wild Rose
10.0 out of 10, Exceptional, (14)
"Great place! "
United States
Heather B.
The price is HK$910
HK$2,707 total
includes taxes & fees
6 Jan - 7 Jan 2026
Lakefront Couples Retreat | Hot Tub & Fireplace
Smart TV
RiverFront Cottage>Private Pier>Firepit & Wildlife

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
The price is HK$624
HK$1,643 total
includes taxes & fees
3 Jan - 4 Jan 2026
RiverFront Cottage>Private Pier>Firepit & Wildlife
Exterior
Lake Camelot | Lakefront | 10 Min to Sand Valley | Snowshoes | Discounted Rates

Lake Camelot | Lakefront | 10 Min to Sand Valley | Snowshoes | Discounted Rates

Lake Camelot | Lakefront | 10 Min to Sand Valley | Snowshoes | Discounted Rates
Nekoosa
9.6 out of 10, Exceptional, (7)
"The cottage was very nice and comfortable. "
United States
Jennifer J.
The price is HK$1,290
HK$3,442 total
includes taxes & fees
14 Jan - 15 Jan 2026
Lake Camelot | Lakefront | 10 Min to Sand Valley | Snowshoes | Discounted Rates
Exterior
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Bagley
9.4 out of 10, Exceptional, (40)
"Great cozy place near the river!"
United States
Clint P.
The price is HK$1,119
HK$2,477 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Exterior
A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (119)
"Great location two blocks off main street. Really neat old house with everything you need, we would definitely stay again!!"
United States
Jeff B.
The price is HK$1,294
HK$1,929 total
includes taxes & fees
3 Jan - 4 Jan 2026
A Comfy Cozy Cottage on Clowney
Terrace/patio
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

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.
The price is HK$1,088
HK$2,835 total
includes taxes & fees
11 Jan - 12 Jan 2026
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
Exterior
Walleye Waters Cottage

Walleye Waters Cottage

Walleye Waters Cottage
Briggsville
10.0 out of 10, Exceptional, (6)
"Everything was clean and the stress was very cute. Only a short drive to the dells"
United States
Sarah C.
The price is HK$847
HK$1,881 total
includes taxes & fees
7 Jan - 8 Jan 2026
Walleye Waters Cottage
Exterior
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
Lyndon Station
9.8 out of 10, Exceptional, (37)
"Very clean property and nice stay. "
United States
Arthur A.
The price is HK$1,294
HK$2,735 total
includes taxes & fees
1 Jan - 2 Jan 2026
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
Exterior
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake
Baraboo
10.0 out of 10, Exceptional, (253)
"The property is very private and lovely. Check in was very simple and host even let us in a little early."
United States
Carla L.
The price is HK$1,827
HK$2,436 total
includes taxes & fees
3 Jan - 4 Jan 2026
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake
Exterior
Mississippi River Front Property with amazing views!

Mississippi River Front Property with amazing views!

Mississippi River Front Property with amazing views!
Harpers Ferry
9.0 out of 10, Wonderful, (12)
"Great location, limited amenities "
United States
Joel T.
Mississippi River Front Property with amazing views!
Interior
Walk to Main St Fond du Lac: Retreat w/ Yard

Walk to Main St Fond du Lac: Retreat w/ Yard

Walk to Main St Fond du Lac: Retreat w/ Yard
3.0 star property
Fond du Lac
9.0 out of 10, Wonderful, (2)
"The rooms were clean and arranged as advertised. The house was secure. We would stay here again!"
United States
Kevin
Walk to Main St Fond du Lac: Retreat w/ Yard
Terrace/patio
Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow
3.0 star property
Winona
10.0 out of 10, Exceptional, (1)
"We had a wonderful time and would defiinitely stay again. "
United States
Julie
The price is HK$1,602
HK$1,788 total
includes taxes & fees
5 Jan - 6 Jan 2026
Big River Escape Parkside Bungalow
Exterior
Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Relaxing Taylor Lake Retreat directly on the Chain of Lakes
Chain O' Lakes
9.0 out of 10, Wonderful, (22)
"The cottage is beautiful - cared for and furnished like a second home. The location is amazing, a large yard overlooking a serene lake. Although it feels like you're in the middle of the woods, it's an easy walk to food, drink and music."
United States
Susan A.
The price is HK$1,015
HK$2,828 total
includes taxes & fees
3 Jan - 4 Jan 2026
Relaxing Taylor Lake Retreat directly on the Chain of Lakes
Exterior
Blue Beach Cottage - 5 Minute Walk to Private Beach!

Blue Beach Cottage - 5 Minute Walk to Private Beach!

Blue Beach Cottage - 5 Minute Walk to Private Beach!
Delavan
9.6 out of 10, Exceptional, (16)
"Highly recommend! The place was very clean and the host was responsive and helpful. "
United States
Marianne Y.
The price is HK$2,116
HK$4,679 total
includes taxes & fees
3 Jan - 4 Jan 2026
Blue Beach Cottage - 5 Minute Walk to Private Beach!
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Nice hotel. Great location."
Millard 3-night trip
Posted 1 day ago
The Madison Concourse Hotel and Governor's Club

Find out more about Southwest Wisconsin

Southwest Wisconsin Cottages information

Number of reviews
654
Accommodation
76 Cottages
Lowest Price
HK$1,643
Highest Price
HK$4,679

Frequently asked questions

How much do cottages in Southwest Wisconsin cost?
Cottages in Southwest Wisconsin range between HK$1,643 and HK$4,679 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southwest Wisconsin?
Southwest Wisconsin has 76 cottages to choose from. Select your travel dates, enter your destination and plan your next escape today.
Why book your cottage in Southwest Wisconsin with Expedia?
Expedia has some terrific cottages in Southwest Wisconsin, so start packing your bags for a memorable holiday close to nature. If you're sticking to a budget, select how much you're willing to spend and the star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right digs whatever your trip looks like.
How can I find cheap cottages in Southwest Wisconsin?
With Expedia's helpful filter tool, booking cheap cottages in Southwest Wisconsin has never been easier. To discover properties that'll make your bank balance smile, refine your search results by star rating, budget and amenities.
What is there to do in Southwest Wisconsin near my cottage?
Whether you enjoy shopping, dining, history or culture, Southwest Wisconsin offers something for everyone! The well-known city of Wisconsin Dells boasts loads of things to do, including Rick Wilcox Magic Theatre, Noah's Ark Waterpark and Timbavati Wildlife Park. If you're escaping to La Crosse, Pettibone Park, Swarthout Museum and Grandad Bluff Park should be on your to-do list.

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