Southern Wisconsin Holiday Rentals

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Our top choices for Southern Wisconsin holiday rentals

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,131 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 AU$173
includes taxes & fees
16 Nov - 17 Nov
Grandstay Residential Suites Hotel - Sheboygan

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (216 reviews)
"Good location"
United States
ANCA
The price is AU$177
includes taxes & fees
14 Dec - 15 Dec
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 AU$206
includes taxes & fees
13 Dec - 14 Dec
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, (3,533 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
The price is AU$272
includes taxes & fees
17 Nov - 18 Nov
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 AU$308
includes taxes & fees
15 Nov - 16 Nov
Mill Creek Hotel

6. 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 AU$201
includes taxes & fees
23 Nov - 24 Nov
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 AU$345
includes taxes & fees
17 Nov - 18 Nov
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 AU$235
includes taxes & fees
14 Nov - 15 Nov
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 AU$221
includes taxes & fees
15 Nov - 16 Nov
Crooked Creek - Relaxation Cabin

10. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
The price is AU$301
includes taxes & fees
15 Nov - 16 Nov
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 AU$204
includes taxes & fees
16 Nov - 17 Nov
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 AU$457
includes taxes & fees
14 Nov - 15 Nov
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 AU$252
includes taxes & fees
19 Nov - 20 Nov
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 AU$296
includes taxes & fees
15 Nov - 16 Nov
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 AU$1,101
includes taxes & fees
18 Nov - 19 Nov
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 AU$405
includes taxes & fees
16 Nov - 17 Nov
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 AU$288
includes taxes & fees
15 Nov - 16 Nov
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 AU$321
includes taxes & fees
18 Nov - 19 Nov
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 AU$252
includes taxes & fees
16 Nov - 17 Nov
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 AU$374
includes taxes & fees
30 Nov - 1 Dec
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.

Find holiday rentals that suit your style

Top Southern Wisconsin Hotel Reviews

Find out more about Southern Wisconsin

Everything you need to know about Southern Wisconsin holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Wisconsin holiday rental for you. At Expedia, you can take your pick from private holiday 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 Southern Wisconsin holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Southern Wisconsin holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southern Wisconsin holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Southern Wisconsin holiday rentals we have chosen for you start as low as AU$119 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Southern Wisconsin rentals

At Expedia, we put the best Southern Wisconsin holiday 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 Southern 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 Southern Wisconsin holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern 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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