Search Cottages in Southwest Wisconsin

    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
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 112 Cottages in Southwest Wisconsin with updated reviews, rates, and availability.

Little House in the Big Woods on the Prairie
Property grounds

Little House in the Big Woods on the Prairie

10.0 out of 10, Exceptional, (79)
"My wife and I enjoyed the stay at the cabin! It was very clean and the location was perfect! Great place to spend a long weekend! "
Little House in the Big Woods on the Prairie
The Harwood House
Fridge, microwave, oven, stovetop

The Harwood House

10.0 out of 10, Exceptional, (61)
"A clean and well kept place to unwind in, with all of the attractions that the driftless area offers."
The Harwood House
Tiny House on the River
Exterior

Tiny House on the River

10.0 out of 10, Exceptional, (58)
"We had an awesome time! Perfect little weekend getaway that we needed! My girlfriend and I were very impressed with the home and how it was equipped for our stay! Definitely recommend, these folks are great people! "
The price is SAR 563
SAR 941 total
includes taxes & fees
9 Jun - 10 Jun
Tiny House on the River
Charming Cottage - park and walk to town for its FUN!
Beach nearby

Charming Cottage - park and walk to town for its FUN!

10.0 out of 10, Exceptional, (144)
"Beautiful big home close to town. All the comforts of home and very convenient to town."
Charming Cottage - park and walk to town for its FUN!
Christmas Mountain Village™ - 2 Bedroom Cottage
A heated pool

Christmas Mountain Village™ - 2 Bedroom Cottage

10.0 out of 10, Exceptional, (1)
"The cabin was nice and clean. Nice location and quiet. Nice place for a family stay."
Christmas Mountain Village™ - 2 Bedroom Cottage
Bear's Den- Cottages On Serenity Lake- Beautiful Cottage On Small, Private Lake!
Outdoor dining

Bear's Den- Cottages On Serenity Lake- Beautiful Cottage On Small, Private Lake!

9.6 out of 10, Exceptional, (114)
"We thoroughly enjoyed the nature and trails, then relaxed in the hot tub and in front of the fireplace. We will be happy to return!"
Bear's Den- Cottages On Serenity Lake- Beautiful Cottage On Small, Private Lake!
Cottage on the river
Terrace/patio

Cottage on the river

9.4 out of 10, Exceptional, (51)
"Great place, as advertised. Perfect for a weekend getaway for 2!"
Cottage on the river
Madison & ~UW~-Madison Area Lakefront Home
On the beach

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (189)
"This house was ideal. Jennifer decorated it for Christmas and it was just perfect! The size, space, decorations and location were just want we wanted. I would highly recommend this spot. "
Madison & ~UW~-Madison Area Lakefront Home
Christmas Mountain Village™ - Wisconsin Dells - 2 Bedroom Cottage
A heated pool

Christmas Mountain Village™ - Wisconsin Dells - 2 Bedroom Cottage

10.0 out of 10, Exceptional, (3)
"Relaxing comfortable vacation"
Christmas Mountain Village™ - Wisconsin Dells - 2 Bedroom Cottage
Pheasant Cottage- Cottages On Serenity Lake- has best view of Serenity Lake!
Fridge, microwave, stovetop, coffee/tea maker

Pheasant Cottage- Cottages On Serenity Lake- has best view of Serenity Lake!

9.8 out of 10, Exceptional, (37)
"Very comfortable cabins Good distance from townNice driveRelaxing hot tubBrian, the just was very attentive to our needs "
Pheasant Cottage- Cottages On Serenity Lake- has best view of Serenity Lake!
Sunny Lane Cottage - Walk to Castle Rock Lake!
Terrace/patio

Sunny Lane Cottage - Walk to Castle Rock Lake!

10.0 out of 10, Exceptional, (40)
"Joni’s rental was clean and supported our needs perfectly. "
Sunny Lane Cottage - Walk to Castle Rock Lake!
Cozy Cabin with a Hot Tub!
Fridge, microwave, oven, stovetop

Cozy Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (22)
"Great place to stay. Plenty of space for our girls weekend. Clean and comfortable. Can't wait to stay again for our next trip "
Cozy Cabin with a Hot Tub!
Eischen Cottage 2 on Lake Delton
Dining

Eischen Cottage 2 on Lake Delton

9.4 out of 10, Exceptional, (16)
"Nice place but get a mini split and end the old window ac plus put in some wifi"
Eischen Cottage 2 on Lake Delton
Down- Home Christmas Mountain Village, 2 Bedroom Cottage
A heated pool

Down- Home Christmas Mountain Village, 2 Bedroom Cottage

8.4 out of 10, Very Good, (13)
"This was our first visit to Christmas Mountain and we all agree it will be a yearly trip. Perfect cottage and friendly staff. "
Down- Home Christmas Mountain Village, 2 Bedroom Cottage
Charming Riverview Cottage Home in Black River Falls
Exterior

Charming Riverview Cottage Home in Black River Falls

10.0 out of 10, Exceptional, (2)
"Breathing taking views of the River, we hiked the trails, seen eagles, woodpeckers, and other birds. The home is beautiful, cozy and has everything stocked with many extra added details that a family would ever want or need for their stay. The cozy fireplace in the living room and the piano was a favorite spot my family enjoyed so much. We all had a wonderful time! "
Charming Riverview Cottage Home in Black River Falls
Charming 2 bedroom 1 bath cottage in Wisconsin Dells
Fridge, microwave, oven, stovetop

Charming 2 bedroom 1 bath cottage in Wisconsin Dells

Charming 2 bedroom 1 bath cottage in Wisconsin Dells
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake
Property grounds

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

10.0 out of 10, Exceptional, (241)
"Daron's contemporary cabin in the woods was amazing. We were very close to Devil's Head Ski Resort and enjoyed a beautiful day of downhill skiing along with Cross Country skiing at Mirror Lake State Park. Everything was perfect!"
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake
Riverfront Home w/ Private Dock in Wisconsin Dells
Interior

Riverfront Home w/ Private Dock in Wisconsin Dells

3.0 star property
Riverfront Home w/ Private Dock in Wisconsin Dells
Chic Wisconsin Retreat w/ Deck, Grill & Fire Pit!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Chic Wisconsin Retreat w/ Deck, Grill & Fire Pit!

3.0 star property
Chic Wisconsin Retreat w/ Deck, Grill & Fire Pit!
Dog Friendly Sand Valley Lake Camelot
Smart TV, fireplace

Dog Friendly Sand Valley Lake Camelot

10.0 out of 10, Exceptional, (2)
"Very comfortable and clean. Great location too."
The price is SAR 750
SAR 1,775 total
includes taxes & fees
2 Jun - 3 Jun
Dog Friendly Sand Valley Lake Camelot
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
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in Southwest Wisconsin cost?
Cottages in Southwest Wisconsin range between SAR 563 and SAR 750 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 112 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.