Search Southwest Wisconsin Cottage Rentals from CA $204

    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
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
In one month
Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Browse Select Southwest Wisconsin Cottages

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, (83)
"What a wonderful spot for a weekend away. "
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, (63)
"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, (62)
"Tom and Verona were great hosts. They answered all of the questions I had and made the check-in process seamless. The cabin was beautiful, clean and cozy, and sat right on the river."
The price is CA $204
CA $337 total
includes taxes & fees
Jul 8 - Jul 9
Tiny House on the River
Cottage on the river
Terrace/patio

Cottage on the river

9.4 out of 10, Exceptional, (53)
"Great place, as advertised. Perfect for a weekend getaway for 2!"
Cottage on the river
Vintage Cottage on Lake Delton
Exterior

Vintage Cottage on Lake Delton

9.4 out of 10, Exceptional, (60)
"Everything was as described...very nice acommodations...enjoyed our visit very much! Would highly recommend !"
Vintage Cottage on Lake Delton
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, (243)
"This was our second time in this house and both times our stay has been excellent. The house has a wonderful open layout with huge windows and cozy fireplace. We hope to stay again in the future."
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
"We were very impressed with this property. All the amenities that were necessary for a comfortable stay were provided by the host. Also, excellent communication with the host as well. We would love to stay another time!"
The price is CA $313
CA $610 total
includes taxes & fees
Jul 14 - Jul 15
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
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, (147)
"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!
Bear's Den- Cottages On Serenity Lake- Beautiful Cottage On Small, Private Lake!
Exterior

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!
Christmas Mountain Village™ - 2 Bedroom Cottage
A heated pool

Christmas Mountain Village™ - 2 Bedroom Cottage

8.0 out of 10, Very good, (2)
"This property was fine to stay at but the host never told us that there was a chance of having to move houses during our stay. He was completely unhelpful in telling me where that was stated in the listing. We also had 2 different houses at this stay and neither where what were in the listing. "
Christmas Mountain Village™ - 2 Bedroom Cottage
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
Madison & ~UW~-Madison Area Lakefront Home
On the beach

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (191)
"We had a wonderful weekend here with family. A beautiful place to stay with gorgeous views of the lake. The house was super clean and felt like home. We cannot wait to go back again! Jennifer was amazing!"
Madison & ~UW~-Madison Area Lakefront Home
Eischen Cottage 2 on Lake Delton
Dining

Eischen Cottage 2 on Lake Delton

9.4 out of 10, Exceptional, (16)
"This was the perfect setup for my wife and I and our 4 children. The fact we got to live the cabin life within a few minutes of all the main Dells attractions was wonderful. We really enjoyed using the kayak, rowboat and fire pit that were on site. We caught lots of fish right off the dock including sunfish, perch, small and large mouth bass. The kids played in the sandy beach and we loved playing board games and eating meals on the big wrap around deck. We would rent this cabin again."
Eischen Cottage 2 on Lake Delton
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, (38)
"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!
Bird House on Wisconsin River
Exterior

Bird House on Wisconsin River

9.6 out of 10, Exceptional, (55)
"A very lovely cabin with a beautiful beachfront view of the Wisconsin River."
Bird House on Wisconsin River
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
Nord Haus on Dell Creek Channel
Exterior

Nord Haus on Dell Creek Channel

9.6 out of 10, Exceptional, (39)
"This place was great for our quick weekend getaway. The location is perfect if you like to be near all of the main attractions."
Nord Haus on Dell Creek Channel
Charming 3-bedroom plus loft cottage on Lake Arrowhead and near Sand Valley!
Living area

Charming 3-bedroom plus loft cottage on Lake Arrowhead and near Sand Valley!

10.0 out of 10, Exceptional, (1)
"Great place for family retreat. Could not have any better lake access. Awesome waterway to enjoy. Would stay again. Bryan"
Charming 3-bedroom plus loft cottage on Lake Arrowhead and near Sand Valley!
Chic Wisconsin Retreat w/ Deck, Grill & Fire Pit!
Fridge, microwave, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (24)
"Our stay was wonderful in this cute little cottage in the woods. This home is beautifully decorated and comes equipped with everything you’ll need. The owners are very organized and have thought of everything. I wish all rentals were this special. Highly recommend!"
Chic Wisconsin Retreat w/ Deck, Grill & Fire Pit!
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
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 CA $204 and CA $313 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 121 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.