Southwest Wisconsin Vacation Rentals from CA $182: Short-Term Rentals for 2026

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Our top choices for Southwest Wisconsin vacation rentals

A cabin with a dining area, a bicycle, and a sign reading "Vangelis".

1. Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

Wild Rose

Jennifer

CA $210 total

includes taxes & fees

Nov 19 - Nov 20

A wooden cabin with a porch, two windows, and a star decoration on the wall.

2. River Road Retreat

Muscoda

Robert S.

CA $306 total

includes taxes & fees

Nov 4 - Nov 5

A wooden cabin surrounded by snow-covered trees.

3. Cabin on the Kickapoo

Readstown

Sujhey B.

CA $437 total

includes taxes & fees

Oct 27 - Oct 28

A living room with a television, a coffee table, a sofa, and a dining area in the background.

4. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro

Tammy

CA $309 total

includes taxes & fees

Oct 26 - Oct 27

Two white hammocks hanging on a wooden porch with a view of a garden.

5. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Lyndon Station

Eukesha

CA $449 total

includes taxes & fees

Oct 25 - Oct 26

A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

6. A Comfy Cozy Cottage on Clowney

Mineral Point

Cindy P.

CA $346 total

includes taxes & fees

Oct 25 - Oct 26

A field of lavender with a path leading through it.

7. Tamarack Point Homestead

Arcadia

Anonymous traveller

CA $165 total

includes taxes & fees

Oct 22 - Oct 23

A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

8. The Dylin

Downtown Madison

ANCA

CA $182 total

includes taxes & fees

Nov 19 - Nov 20

A lakeside view with beach chairs and a dock.

9. The Docksider - Couples & Young Families - Lakefront!

Lake Delton

Ryan H.

CA $276 total

includes taxes & fees

Oct 25 - Oct 26

A cozy log cabin interior with a fireplace, a sofa, and a large window offering a view of the outdoors.

10. Tiny House on the River

Black River Falls

Scott and Ann G.

CA $325 total

includes taxes & fees

Oct 22 - Oct 23

A beach with sun loungers and a view of a lake.

11. Top Floor Retreat at Delton Grand

Lake Delton

Matt J.

CA $308 total

includes taxes & fees

Oct 25 - Oct 26

A waterfront hotel with multiple buildings, docked boats, and a surrounding forested area.

12. Dells Lakefront Escape - Couples or Families

Lake Delton

Tymica W.

CA $311 total

includes taxes & fees

Oct 25 - Oct 26

A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

13. Colorful getaway in friendly Driftless village

Wonewoc

Emily B.

CA $369 total

includes taxes & fees

Oct 22 - Oct 23

A lakeside view with a dock, picnic tables, and chairs.

14. Piers & Pines at Island Pointe

Wisconsin Dells

Alisia

CA $317 total

includes taxes & fees

Oct 26 - Oct 27

A waterfront hotel with multiple buildings, a dock, and a swimming pool.

15. Sandy Toes at Lighthouse Cove

Lake Delton

Katherine A.

CA $281 total

includes taxes & fees

Oct 26 - Oct 27

A hot tub on a wooden deck with a view of a lake and trees.

16. Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Eastman

Nick C.

CA $415 total

includes taxes & fees

Nov 15 - Nov 16

A grey door with a window above it and a doorbell on the right side.

17. Cozy first floor at the heart of downtown Viroqua

Viroqua

Pete G.

CA $267 total

includes taxes & fees

Oct 26 - Oct 27

A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

18. Your adventure begins the second you arrive!

Norwalk

Betsy D.

CA $331 total

includes taxes & fees

Oct 22 - Oct 23

A modern kitchen with wooden cabinets, stainless steel appliances, and a welcome sign.

19. Harrison's Hideaway at Tamarack - Great Location!

Wisconsin Dells

Jennifer S.

CA $444 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

20. The Willow at Treetop Villas

Lake Delton

Heinrich J.

CA $780 total

includes taxes & fees

Oct 22 - Oct 23

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Top Southwest Wisconsin Hotel Reviews

Natura Treescape Resort

8/10 Good

"Cool place to travel with kids. The cabins are tiny but clean!"

Great Wolf Lodge Wisconsin Dells

8/10 Good

"Staff was great. Especially Dave in Maintenance! We could barely open the patio sliding door and he helped. Staff was nice. Beds were comfy and water pressure in the shower was good. But common spaces, like the main stairs really needed a good vacuuming. For the price I expected more. Wouldn't likely stay again based on what we paid."

AmericInn by Wyndham Madison West

10/10 Excellent

"This is our 2nd time staying here, and it will be our go-to while our kid is at UW Madison. It's not fancy, but it is clean, pretty updated, affordable, an easy drive to campus, close to a ton of restaurants and shopping, the beds are comfortable, and the breakfast is shockingly good for a basic hotel. Tons of options for breakfast and everything is really good and restocked often. It is also consistently lower priced that other area hotels. We will be back!"

Valued Stay Madison

8/10 Good

"In reality, this is a solid 3 stars. Nothing stood out enough to make it a 4 or 5, but nothing was bad enough to warrant a 1 or 2. I officially clicked 4 stars because anything below 4 is seen as "bad" on a review site. Cleanliness: the toilet, shower, floor, linens, shower, desk, fridge, microwave were all clean. There was a spot of something on the bathroom wall (all the walls seem to have been painted within the last few years), but washing down all the walls seems like expecting a lot. Comfort: the heat/AC worked well, the bed was fairly comfortable, and the linens were soft enough. The pillows were great an numerous. Ambiance: there's nothing exciting to look at out the window. This is a utility hotel. Most nights were quiet but there seemed to be people slamming doors all night one night. I never felt unsafe or uncomfortable. Parking seemed tight, especially if I got in later, but I found a spot each night. I could not smell the garbage dump (mid-October weather probably helped). Breakfast: exactly what I would expect from this type of hotel if not for all the reviews praising it. In fairness, I only went on Thurs/Fri, and there just weren't a lot of appealing options for a light meal. I think there were more options on Saturday/Sunday, but I skipped breakfast those days. Overall: as a single person going to an event at the Alliant Energy Center, this was a great choice. I will almost certainly pick the same hotel next year. With family I'd pick some place nicer."

Find out more about Southwest Wisconsin

Everything you need to know about Southwest Wisconsin vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Wisconsin vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Wisconsin vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Wisconsin vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Wisconsin. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Wisconsin vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Wisconsin vacation rentals we have selected for you start as low as CA $182 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southwest Wisconsin rentals

At Expedia, we put the best Southwest Wisconsin vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southwest Wisconsin rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Wisconsin vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Wisconsin. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Southwest Wisconsin vacation rentals

1. Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

2. River Road Retreat

3. Cabin on the Kickapoo

4. Hillsboro Driftless Guesthouse is cozy and ready for you!

5. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

6. A Comfy Cozy Cottage on Clowney

7. Tamarack Point Homestead

8. The Dylin

9. The Docksider - Couples & Young Families - Lakefront!

10. Tiny House on the River

11. Top Floor Retreat at Delton Grand

12. Dells Lakefront Escape - Couples or Families

13. Colorful getaway in friendly Driftless village

14. Piers & Pines at Island Pointe

15. Sandy Toes at Lighthouse Cove

16. Sunset Studio, Amazing River Views, HOT TUB! New Listing!

17. Cozy first floor at the heart of downtown Viroqua

18. Your adventure begins the second you arrive!

19. Harrison's Hideaway at Tamarack - Great Location!

20. The Willow at Treetop Villas

Find vacation rentals that suit your style

Top Southwest Wisconsin Hotel Reviews

Natura Treescape Resort

Find out more about Southwest Wisconsin

Explore a world of travel with Expedia

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