Search Cottages in Southwest Wisconsin

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Cottages in Southwest Wisconsin

Tiny House on the River

10.0 out of 10, Exceptional, (71)
"Lovely cottage. Owners very responsive. We enjoyed our stay."
The price is SAR 563
SAR 941 total
includes taxes & fees
4 Sep - 5 Sep
Tiny House on the River

RiverFront Cottage>Private Pier>Firepit & Wildlife

10.0 out of 10, Exceptional, (33)
"Beautiful place, definitely gives a cozy vibes. Good location. We had a wonderful stay, we will definitely book here again in the future. "
RiverFront Cottage>Private Pier>Firepit & Wildlife

Studio Cottage at Lake Road Campground, near the beautiful Mississippi River.

8.0 out of 10, Very Good, (5)
"We loved the cleanliness, location, quietness, and friendliness of the property manager. It was a great value for the money. We will stay again and we highly recommend!"
The price is SAR 450
SAR 595 total
includes taxes & fees
7 Sep - 8 Sep
Studio Cottage at Lake Road Campground, near the beautiful Mississippi River.

Walleye Waters Cottage

10.0 out of 10, Exceptional, (6)
"Cute cabin! Perfect for our needs. It was clean, quiet location, and very comfortable. The manager was ver responsive and super helpful. I will definitely stay again if in the area."
The price is SAR 405
SAR 904 total
includes taxes & fees
3 Sep - 4 Sep
Walleye Waters Cottage

A Comfy Cozy Cottage on Clowney

9.6 out of 10, Exceptional, (110)
"Comfortable, easy stay for a weekend. "
The price is SAR 507
SAR 784 total
includes taxes & fees
3 Sep - 4 Sep
A Comfy Cozy Cottage on Clowney

Final Summer Bash -Pier, SUP, Kayaks, Games & Fire

9.6 out of 10, Exceptional, (5)
"Becky has gone above and beyond,all you need is clothes and your food.The sunsets are breathtaking and all the amenities.And I am a big coffee drinker so to see how Becky had all that at the house was a big plus for me."
Final Summer Bash -Pier, SUP, Kayaks, Games & Fire

Opal Little Lodge - Luxury Stay with a Panoramic Tree Top View

10.0 out of 10, Exceptional, (6)
"Was a great weekend getaway with my new fiancé, good communication with the manager and cabin was perfect for the two of us!"
The price is SAR 779
SAR 1,107 total
includes taxes & fees
1 Oct - 2 Oct
Opal Little Lodge - Luxury Stay with a Panoramic Tree Top View

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

9.4 out of 10, Exceptional, (31)
"We really enjoyed our stay!"
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

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

10.0 out of 10, Exceptional, (7)
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

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...
Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

Charming A-Frame Cottage, HOT TUB, Fire Pit, Near GOLF & Lakes, 35min to Dells!

10.0 out of 10, Exceptional, (2)
"Kathy’s house is just perfect - beautifully decorated, super cozy, and full of charm. Every detail feels intentional, from the comfy furniture to the stylish touches throughout. A peaceful, picture-perfect retreat you won’t want to leave!"
The price is SAR 843
SAR 1,594 total
includes taxes & fees
7 Sep - 8 Sep
Charming A-Frame Cottage, HOT TUB, Fire Pit, Near GOLF & Lakes, 35min to Dells!

Secluded luxury accommodations with woodland pond view and private hiking trails

10.0 out of 10, Exceptional, (26)
"Our stay was perfect. We enjoyed how secluded and clean the place was. It had everything we needed and more. The bathroom is something to get used to but overall the stay and everything was perfect!"
The price is SAR 779
SAR 1,107 total
includes taxes & fees
3 Sep - 4 Sep
Secluded luxury accommodations with woodland pond view and private hiking trails

Dog Friendly Sand Valley Lake Camelot

10.0 out of 10, Exceptional, (5)
"Christie was great to work with and she promised us a 5-star experience and delivered. The location of the property is in a nice, wooded area near a lake and close to shopping, golf and restaurants. The house is new and very well appointed. The beds are very comfortable, and linens/towels are top notch. The bathrooms are definitely 5-star as my wife loved the mirrors that light up. The extras we appreciated were a Keurig coffee maker (with decaf coffee), an outdoor grill and gas firepit. ...
The price is SAR 799
SAR 1,937 total
includes taxes & fees
8 Sep - 9 Sep
Dog Friendly Sand Valley Lake Camelot

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

9.8 out of 10, Exceptional, (34)
"Great place for family to reconnect with each other ❤️"
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Mississippi River Front Property with amazing views!

9.0 out of 10, Wonderful, (10)
"The property was exactly what we were looking for during our fall weekend gateway. We enjoyed the exceptional view of the Mississippi in the morning. And the hot tub at night. Great and easy communication with the property manager. We would come back again in a heart beat. "
Mississippi River Front Property with amazing views!

Studio cottage at Lake Road Campground, near the Majestic Mississippi River.

9.6 out of 10, Exceptional, (4)
"We did hiking at the state park, went for a drive north along river. Stopped at 2 wineries. Nice area."
The price is SAR 450
SAR 595 total
includes taxes & fees
15 Sep - 16 Sep
Studio cottage at Lake Road Campground, near the Majestic Mississippi River.

Big River Escape Parkside Bungalow

3.0 star property
The price is SAR 642
SAR 717 total
includes taxes & fees
7 Sep - 8 Sep
Big River Escape Parkside Bungalow

Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.

8.8 out of 10, Excellent, (3)
"Had everything we needed & then some! So cozy & charming, perfect for my weekend trip!"
The price is SAR 365
SAR 832 total
includes taxes & fees
8 Sep - 9 Sep
Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.

Cozy cottage on the Fox River, in town location

10.0 out of 10, Exceptional, (3)
"It was exactly what we were looking for. Had everything we needed. "
The price is SAR 630
SAR 981 total
includes taxes & fees
3 Sep - 4 Sep
Cozy cottage on the Fox River, in town location

Relax. Recharge. Reconnect.

2.0 star property
10.0 out of 10, Exceptional, (7)
"We were in town for a volleyball tournament and could not have been happier with our stay here! We felt very safe and welcome and the home owner was very responsive and accommodating. Property is clean and really has that homey feel with lots of natural light and comfortable beds. The shower head is amazing and felt like a massage! This is also in a cute little town with a bar/restaurant just blocks away that has excellent food. We will definitely stay here any time we are in the area. Very...
The price is SAR 1,218
SAR 1,477 total
includes taxes & fees
12 Sep - 13 Sep
Relax. Recharge. Reconnect.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Wisconsin Hotel Reviews

Frequently asked questions

How much do cottages in Southwest Wisconsin cost?
Cottages in Southwest Wisconsin range between SAR 563 and SAR 563 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 127 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.