A lighthouse and a house with a red roof.

Southern Wisconsin Holiday Rentals

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Our top choices for Southern Wisconsin holiday 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, (123 reviews)
"We loved everything about this property! Definitely will be going back!"
United States
Ashley
The price is NZ$269
includes taxes & fees
15 Sept - 16 Sept
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

2. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,071 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is NZ$240
includes taxes & fees
1 Sept - 2 Sept
Grandstay Residential Suites Hotel - Sheboygan

3. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (48 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is NZ$322
includes taxes & fees
18 Aug - 19 Aug
Gleason's Chouse

4. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (173 reviews)
"Staying at this house was like staying at my grandmother’s house when I was a child. It was a wonderful experience, and the grounds were phenomenal."
United States
Jeff
The price is NZ$285
includes taxes & fees
18 Aug - 19 Aug
Country home with flowing river

5. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,377 reviews)
"It was a perfect little getaway for the family"
United States
Summer
The price is NZ$391
includes taxes & fees
1 Sept - 2 Sept
Timber Ridge Lodge and Waterpark

6. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
The price is NZ$383
includes taxes & fees
18 Aug - 19 Aug
Your adventure begins the second you arrive!

7. Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"Worked well for our 2-day stay. "
United States
John V.
The price is NZ$325
includes taxes & fees
24 Aug - 25 Aug
Crooked Creek - Serenity Cabin

8. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (101 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is NZ$272
includes taxes & fees
20 Aug - 21 Aug
The Bungaleau 1 Bedroom House In Cute Rivertown

9. Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
7.0 out of 10, Good, (4 reviews)
"Me and my brother had an incredible time here. It was exactly what we were looking for. From the staff, to the property and the room itself. The natures walls close by. It was great and will be returning with more of the family again."
United States
Jessica
The price is NZ$306
includes taxes & fees
18 Aug - 19 Aug
Tiki Beach Campground

10. RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife
Princeton
10.0 out of 10, Exceptional, (44 reviews)
"Cute property nicely located overlooking a beautiful marsh and river! Definitely recommend. Great value. Perfect for a couple. Recommended to host that window coverings be placed over picture window and patio door as well for privacy and security on riverside."
United States
Victoria J.
The price is NZ$467
includes taxes & fees
27 Aug - 28 Aug
RiverFront Cottage>Private Pier>Firepit & Wildlife

11. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (42 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is NZ$199
includes taxes & fees
23 Aug - 24 Aug
Tamarack Point Homestead

12. Yukon Trails RV & Camping Resort

Yukon Trails RV & Camping Resort
2.0 star property
Lyndon Station
8.8 out of 10, Excellent, (5 reviews)
"My family and I love this place. This was our second time at Yukon Trails. We will be back for sure. "
United States
Alessandra
The price is NZ$378
includes taxes & fees
19 Aug - 20 Aug
Yukon Trails RV & Camping Resort

13. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (235 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
The price is NZ$365
includes taxes & fees
11 Sept - 12 Sept
Country Living at its Finest

14. River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (30 reviews)
"Will for sure stay again "
United States
Nicole
The price is NZ$405
includes taxes & fees
18 Aug - 19 Aug
River Road Retreat

15. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (133 reviews)
"An beautiful home with an interesting history right by the lovely downtown. We thoroughly enjoyed our stay, as we felt welcome and comfortable."
United States
Tashia N.
The price is NZ$415
includes taxes & fees
18 Aug - 19 Aug
A Comfy Cozy Cottage on Clowney

16. 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, (91 reviews)
"Great stay overall."
United States
Keelie D.
The price is NZ$382
includes taxes & fees
19 Aug - 20 Aug
Ohio Street Retreat-hot tub, pool, massage chair

17. Blue Lakeview Home

Blue Lakeview Home
Edgerton
The price is NZ$451
includes taxes & fees
24 Aug - 25 Aug
Blue Lakeview Home

18. Charming cottage on Lake Winnebago

Charming cottage on Lake Winnebago
Neenah
10.0 out of 10, Exceptional, (57 reviews)
"Amazing stay and accommodation!!"
United States
Samuel W.
The price is NZ$872
includes taxes & fees
23 Aug - 24 Aug
Charming cottage on Lake Winnebago

19. MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (110 reviews)
"Best location and fabulous hospitality!"
United States
Anne B.
The price is NZ$463
includes taxes & fees
23 Aug - 24 Aug
MJ's Penthouse ,a piece of paradise on Monroe's historic square

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

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (29 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is NZ$358
includes taxes & fees
18 Aug - 19 Aug
Hillsboro Driftless Guesthouse is cozy and ready for you!
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southern Wisconsin holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southern Wisconsin. 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 Southern Wisconsin. 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 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 holiday 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 Southern Wisconsin short-term rentals, that won’t be hard to do.

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