Search Cottages in Southwest Wisconsin

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Check prices for these dates

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

Cottages in Southwest Wisconsin

Exterior
Tiny House on the River

Cottage in 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.
The price is AED 446
AED 783 total
includes taxes & fees
10 Dec - 11 Dec
Tiny House on the River
Smart TV
RiverFront Cottage>Private Pier>Firepit & Wildlife

Cottage in 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 AED 344
AED 835 total
includes taxes & fees
11 Dec - 12 Dec
RiverFront Cottage>Private Pier>Firepit & Wildlife
Property grounds
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Cottage in Milton

2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute! Near winery and a supper club! "
United States
Juanita W.
The price is AED 364
AED 728 total
includes taxes & fees
12 Dec - 13 Dec
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
Exterior
A Comfy Cozy Cottage on Clowney

Cottage in Mineral Point

9.6 out of 10, Exceptional, (118)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is AED 496
AED 767 total
includes taxes & fees
20 Dec - 21 Dec
A Comfy Cozy Cottage on Clowney
Exterior
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cottage in Bagley

9.4 out of 10, Exceptional, (40)
"Great cozy place near the river!"
United States
Clint P.
The price is AED 529
AED 1,170 total
includes taxes & fees
11 Dec - 12 Dec
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Terrace/patio
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Cottage in 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 AED 514
AED 1,347 total
includes taxes & fees
10 Dec - 11 Dec
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
Exterior
Walleye Waters Cottage

Cottage in 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 AED 397
AED 877 total
includes taxes & fees
10 Dec - 11 Dec
Walleye Waters Cottage
Property grounds
Final Summer Bash -Pier, SUP, Kayaks, Games & Fire

Cottage in Wautoma

9.8 out of 10, Exceptional, (7)
"We enjoyed our stay. Everything was very well stocked. Plenty of supplies, and nice little surprises that were a nice extra touch. "
United States
Natalie A.
The price is AED 364
AED 1,268 total
includes taxes & fees
10 Dec - 11 Dec
Final Summer Bash -Pier, SUP, Kayaks, Games & Fire
Exterior
Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

Cottage in Merrimac

8.0 out of 10, Very Good, (1)
"Owner accidently gave us the wrong door code, but mistakes happen and we problem solved.Inside was even nicer & updated from photos shown overall and the space was perfect for what we needed.I do not believe the description was fully complete. It said Bluff Views which I didn't see which was fine, but I was NOT expecting this tiny house to be in a parking lot adjacent of a bar/venue. The one photo of the ouside is clearly photoshopped into blue sky, but it is really a blue bar.Our stay was...
United States
Sheri M.
The price is AED 533
AED 917 total
includes taxes & fees
10 Dec - 11 Dec
Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries
Exterior
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Cottage in Lyndon Station

9.8 out of 10, Exceptional, (36)
"Very clean property and nice stay. "
United States
Arthur A.
The price is AED 679
AED 1,376 total
includes taxes & fees
1 Jan - 2 January 2026
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
Terrace/patio
Dog Friendly Sand Valley Lake Camelot

Cottage in Nekoosa

10.0 out of 10, Exceptional, (5)
"Great spot to stay with friends close to sand valley. Plenty of space for our group and a very nice set up. "
United States
Justin L.
The price is AED 782
AED 1,896 total
includes taxes & fees
10 Dec - 11 Dec
Dog Friendly Sand Valley Lake Camelot
Exterior
Mississippi River Front Property with amazing views!

Cottage in Harpers Ferry

9.0 out of 10, Wonderful, (12)
"Great location, limited amenities "
United States
Joel T.
The price is AED 1,285
AED 2,094 total
includes taxes & fees
10 Dec - 11 Dec
Mississippi River Front Property with amazing views!
Outdoor dining
Cozy lakefront cabin on Fox Lake with great fishing, bar, and hot tub!

Cottage in Fox Lake

2.0 star property
The price is AED 1,175
AED 2,302 total
includes taxes & fees
11 Dec - 12 Dec
Cozy lakefront cabin on Fox Lake with great fishing, bar, and hot tub!
House (2 Bedrooms) | Interior
Walk to Main St Fond du Lac: Retreat w/ Yard

Cottage in Fond du Lac

3.0 star property
8.0 out of 10, Very Good, (1)
"There was a terrible smell in the house. Smelled smoky, even though there were "No Smoking" signs posted in several places. I bought a neutralizing spray and used it every time we entered and exited. It helped a little. Beds were comfortable. We were cold the first night because I didn't know right away how to adjust the thermostat. Shower was new and nice. We arrived in the dark and there was a couple of "scary" people on the front steps. It felt safer in the daylight. "
United States
terri
The price is AED 316
AED 766 total
includes taxes & fees
10 Dec - 11 Dec
Walk to Main St Fond du Lac: Retreat w/ Yard
Family Cottage, Park View | Terrace/patio
Big River Escape Parkside Bungalow

Cottage in Winona

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a wonderful time and would defiinitely stay again. "
United States
Julie
The price is AED 799
AED 892 total
includes taxes & fees
14 Dec - 15 Dec
Big River Escape Parkside Bungalow
Exterior
Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Cottage in Chain O' Lakes

9.0 out of 10, Wonderful, (22)
"Overall a nice stay. Had what we needed, and was an enjoyable time for our family. "
United States
Andrew W.
The price is AED 479
AED 1,336 total
includes taxes & fees
10 Dec - 11 Dec
Relaxing Taylor Lake Retreat directly on the Chain of Lakes
Property grounds
Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.

Cottage in Cherry Valley

9.8 out of 10, Exceptional, (13)
"Had everything we needed & then some! So cozy & charming, perfect for my weekend trip!"
United States
Mia E.
The price is AED 331
AED 782 total
includes taxes & fees
10 Dec - 11 Dec
Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.
Outdoor dining
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access

Cottage in The Galena Territory

10.0 out of 10, Exceptional, (13)
"Cute little house, great location! "
United States
Sandra G.
The price is AED 414
AED 1,108 total
includes taxes & fees
10 Dec - 11 Dec
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
Exterior
Blue Beach Cottage - 5 Minute Walk to Private Beach!

Cottage in 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 AED 1,000
AED 2,227 total
includes taxes & fees
10 Dec - 11 Dec
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
"Excellent all around every time "
Christa 2-night trip
Posted 11 hours ago
The Madison Concourse Hotel and Governor's Club

Frequently asked questions

How much do cottages in Southwest Wisconsin cost?
Cottages in Southwest Wisconsin range between AED 728 and AED 2,227 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 vacay 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.

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