A lighthouse and a house with a red roof.

Southern Wisconsin Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southern Wisconsin vacation rentals

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

Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
2.0 star property
Wild Rose
9.8 out of 10, Exceptional, (160 reviews)
"Absolutely amazing little getaway"
United States
Alyssa
The price is CA $131
CA $198 total
includes taxes & fees
Dec 8 - Dec 9
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (212 reviews)
"Good location"
United States
ANCA
The price is CA $156
CA $180 total
includes taxes & fees
Nov 19 - Nov 20
The Dylin

3. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,127 reviews)
"Quiet place near the lake."
United States
Vivian
The price is CA $170
CA $192 total
includes taxes & fees
Nov 10 - Nov 11
Grandstay Residential Suites Hotel - Sheboygan

4. Top Floor Retreat at Delton Grand

Top Floor Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (45 reviews)
"Our stay at Delton Grand top floor was perfect. The view of lake Delton was amazing. The facilities were excellent and we would definitely book again."
United States
Kenneth
The price is CA $129
CA $317 total
includes taxes & fees
Nov 11 - Nov 12
Top Floor Retreat at Delton Grand

5. Luxury Beachfront Retreat at Delton Grand

Luxury Beachfront Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (24 reviews)
"Perfect Lakeview!"
United States
Jacob
The price is CA $111
CA $296 total
includes taxes & fees
Nov 18 - Nov 19
Luxury Beachfront Retreat at Delton Grand

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

Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Eastman
9.4 out of 10, Exceptional, (22 reviews)
"Loved it will be back!"
United States
Nick C.
The price is CA $191
CA $396 total
includes taxes & fees
Nov 15 - Nov 16
Sunset Studio, Amazing River Views, HOT TUB! New Listing!

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (235 reviews)
"Amazing property right on the water, great location, fully recommend!"
United States
Ryan H.
The price is CA $107
CA $273 total
includes taxes & fees
Nov 15 - Nov 16
The Docksider - Couples & Young Families - Lakefront!

8. Sandy Toes at Lighthouse Cove

Sandy Toes at Lighthouse Cove
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"This unit is great right off Lake Delton very peaceful and comfortable."
United States
David B.
The price is CA $100
CA $266 total
includes taxes & fees
Nov 10 - Nov 11
Sandy Toes at Lighthouse Cove

9. Comfy Views Condo - Delton Grand 423

Comfy Views Condo - Delton Grand 423
Lake Delton
9.8 out of 10, Exceptional, (35 reviews)
"Christopher the host was out of this world great, he answered all my sometimes borderline silly questions very quickly, the place is beautiful and super clean, and a perfect location! Thanks so much for letting us stay in your awesome condo."
United States
Jon
The price is CA $116
CA $301 total
includes taxes & fees
Nov 10 - Nov 11
Comfy Views Condo - Delton Grand 423

10. Piers & Pines at Island Pointe

Piers & Pines at Island Pointe
Wisconsin Dells
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay. Perfect little cabin and hosts were very helpful."
United States
Alisia
The price is CA $127
CA $301 total
includes taxes & fees
Nov 10 - Nov 11
Piers & Pines at Island Pointe

11. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is CA $120
CA $174 total
includes taxes & fees
Dec 1 - Dec 2
A Room with a View

12. Dells Lakefront Escape - Couples or Families

Dells Lakefront Escape - Couples or Families
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"Good location, easy check in! The indoor pool was closed during our stay but we were notified in plenty of time and it was no big deal!"
United States
Tymica W.
The price is CA $116
CA $286 total
includes taxes & fees
Nov 10 - Nov 11
Dells Lakefront Escape - Couples or Families

13. Ohio Street Retreat-hot tub, pool, massage chair

Ohio Street Retreat-hot tub, pool, massage chair
Prairie du Chien
10.0 out of 10, Exceptional, (100 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is CA $168
CA $285 total
includes taxes & fees
Nov 15 - Nov 16
Ohio Street Retreat-hot tub, pool, massage chair

14. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (40 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is CA $92
CA $123 total
includes taxes & fees
Nov 11 - Nov 12
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

15. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is CA $148
CA $174 total
includes taxes & fees
Nov 24 - Nov 25
Tamarack Point Homestead

16. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,264 reviews)
"This place was very comfortable an cozy an the food in the cafe was amazing definitely worth the money an ill be staying there again"
United States
Savannah
The price is CA $203
CA $240 total
includes taxes & fees
Nov 22 - Nov 23
The Plaza Hotel

17. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,527 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
The price is CA $137
CA $208 total
includes taxes & fees
Dec 9 - Dec 10
Timber Ridge Lodge and Waterpark

18. Lake Geneva, Fireplace, Pool, Wifi, King Bed

Lake Geneva, Fireplace, Pool, Wifi, King Bed
Lake Geneva
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful area with great shops and food."
United States
SUZY R.
The price is CA $130
CA $356 total
includes taxes & fees
Nov 10 - Nov 11
Lake Geneva, Fireplace, Pool, Wifi, King Bed

19. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (182 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is CA $196
CA $225 total
includes taxes & fees
Nov 10 - Nov 11
Country home with flowing river

20. Beachtop Condo at Delton Grand - Waterfront

Beachtop Condo at Delton Grand - Waterfront
Lake Delton
10.0 out of 10, Exceptional, (42 reviews)
"Excellent communication and a wonderful place to stay. My family had a great time, and we would certainly consider returning in the future."
United States
Rishi
The price is CA $154
CA $465 total
includes taxes & fees
Nov 10 - Nov 11
Beachtop Condo at Delton Grand - Waterfront
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 Southern Wisconsin Hotel Reviews

Find out more about Southern Wisconsin

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Southern Wisconsin. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia