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Southern Wisconsin Vacation Rentals

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Our top choices for Southern Wisconsin vacation rentals

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,133 reviews)
"Was a very nice stay, hotel room was nice and staff was very helpful and friendly. Will definitely be coming back"
United States
Maxim
The price is CA $149
CA $169 total
includes taxes & fees
Nov 15 - Nov 16
Grandstay Residential Suites Hotel - Sheboygan

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (217 reviews)
"Good location"
United States
ANCA
The price is CA $150
CA $173 total
includes taxes & fees
Dec 14 - Dec 15
The Dylin

3. 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, (162 reviews)
"Great place to spend outdoors, staff are friendly and always there if anything is needed."
United States
Brenda
The price is CA $133
CA $200 total
includes taxes & fees
Dec 13 - Dec 14
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

4. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,535 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
The price is CA $193
CA $271 total
includes taxes & fees
Nov 18 - Nov 19
Timber Ridge Lodge and Waterpark

5. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,276 reviews)
"clean, comfortable and great location"
United States
Marshall
The price is CA $265
CA $301 total
includes taxes & fees
Nov 15 - Nov 16
Mill Creek Hotel

6. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,266 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 $189
CA $223 total
includes taxes & fees
Dec 15 - Dec 16
The Plaza Hotel

7. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (142 reviews)
"This is such a charming and unique old place, and right next to downtown. What a perfect location in one of the most charming and welcoming towns you'll ever visit!"
United States
Cindy P.
The price is CA $238
CA $321 total
includes taxes & fees
Nov 15 - Nov 16
A Comfy Cozy Cottage on Clowney

8. 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 $198
CA $217 total
includes taxes & fees
Nov 28 - Nov 29
Country home with flowing river

9. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (14 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is CA $126
CA $213 total
includes taxes & fees
Nov 15 - Nov 16
Crooked Creek - Relaxation Cabin

10. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"Nice little place with a good location near the river."
United States
matthew g.
The price is CA $257
CA $295 total
includes taxes & fees
Nov 24 - Nov 25
River Road Retreat

11. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
The price is CA $180
CA $197 total
includes taxes & fees
Nov 16 - Nov 17
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

12. Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
8.8 out of 10, Excellent, (68 reviews)
"Very nice condo, clean and spacious. Loved spending time on the balcony watching the busy street. Host was very responsive and nice. Lots of near by shops and fun things. Very secure building, overall nice stay."
United States
Jenna N.
The price is CA $321
CA $452 total
includes taxes & fees
Nov 16 - Nov 17
Downtown Eastside gem near Fiserv Forum Water St Brady St

13. Stylish 1 bedroom cottage along the Mississippi River

Stylish 1 bedroom cottage along the Mississippi River
Stoddard
9.6 out of 10, Exceptional, (39 reviews)
"Very nice and clean property. Private location."
United States
Kevin
The price is CA $212
CA $243 total
includes taxes & fees
Nov 19 - Nov 20
Stylish 1 bedroom cottage along the Mississippi River

14. 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 $169
CA $287 total
includes taxes & fees
Nov 15 - Nov 16
Ohio Street Retreat-hot tub, pool, massage chair

15. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
The price is CA $180
CA $1,097 total
includes taxes & fees
Nov 18 - Nov 19
Modern Lake Geneva Condo With Views

16. 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 $201
CA $411 total
includes taxes & fees
Nov 15 - Nov 16
Sunset Studio, Amazing River Views, HOT TUB! New Listing!

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (236 reviews)
"Amazing property right on the water, great location, fully recommend!"
United States
Ryan H.
The price is CA $108
CA $276 total
includes taxes & fees
Nov 15 - Nov 16
The Docksider - Couples & Young Families - Lakefront!

18. 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 $106
CA $288 total
includes taxes & fees
Nov 15 - Nov 16
Luxury Beachfront Retreat at Delton Grand

19. Top location, no cleaning fee, everthings close B

Top location, no cleaning fee, everthings close B
Lake Geneva
10.0 out of 10, Exceptional, (81 reviews)
"Great location and cozy place!"
United States
Justin G.
The price is CA $198
CA $244 total
includes taxes & fees
Nov 16 - Nov 17
Top location, no cleaning fee, everthings close B

20. Piers & Pines at Island Pointe

Piers & Pines at Island Pointe
Wisconsin Dells
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful stay. Perfect little cabin and hosts were very helpful."
United States
Alisia
The price is CA $177
CA $364 total
includes taxes & fees
Nov 30 - Dec 1
Piers & Pines at Island Pointe
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.
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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.

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