A lighthouse and a house with a red roof.

Southern Wisconsin Holiday 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 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, (1,095 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is NZ$242
includes taxes & fees
1 Nov - 2 Nov
Grandstay Residential Suites Hotel - Sheboygan

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
The price is NZ$229
includes taxes & fees
1 Nov - 2 Nov
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, (144 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
The price is NZ$264
includes taxes & fees
1 Nov - 2 Nov
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, (3,462 reviews)
"I love this place"
United States
Edgar
The price is NZ$297
includes taxes & fees
21 Oct - 22 Oct
Timber Ridge Lodge and Waterpark

5. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,264 reviews)
"Super friendly staff, perfect hotel for romantic gateway."
United States
Daniel
The price is NZ$375
includes taxes & fees
1 Nov - 2 Nov
Mill Creek Hotel

6. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,253 reviews)
"Parking was reasonable and close by"
United States
Danita
The price is NZ$340
includes taxes & fees
26 Oct - 27 Oct
The Plaza Hotel

7. 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 NZ$380
includes taxes & fees
2 Oct - 3 Oct
River Road Retreat

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (235 reviews)
"The Lake Delton Docksider condo was clean, comfortable, and located close to all Wisconsin Dells attractions. We enjoyed sitting on the balcony and watching the boats pass by. Communication with the property manager was great and we had no issues."
United States
Tom T.
The price is NZ$348
includes taxes & fees
13 Oct - 14 Oct
The Docksider - Couples & Young Families - Lakefront!

9. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (138 reviews)
"The cottage was very quaint and comfortable. Great location for exploring downtown Mineral Point on foot. Had a fun stay."
United States
Rick C.
The price is NZ$434
includes taxes & fees
4 Oct - 5 Oct
A Comfy Cozy Cottage on Clowney

10. Top Floor Retreat at Delton Grand

Top Floor Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (43 reviews)
"Everything was good. Definitely would stay again. "
United States
Matt J.
The price is NZ$382
includes taxes & fees
5 Oct - 6 Oct
Top Floor Retreat at Delton Grand

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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is NZ$307
includes taxes & fees
7 Oct - 8 Oct
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

12. Arrowhead Resort Campground

Arrowhead Resort Campground
2.0 star property
Wisconsin Dells
7.8 out of 10, Good, (47 reviews)
"Clean, well maintained cottage. Comfy beds. Super close to downtown activities."
United States
Alexis
The price is NZ$234
includes taxes & fees
5 Oct - 6 Oct
Arrowhead Resort Campground

13. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (177 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is NZ$298
includes taxes & fees
5 Oct - 6 Oct
Country home with flowing river

14. RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife
Princeton
10.0 out of 10, Exceptional, (46 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$423
includes taxes & fees
5 Oct - 6 Oct
RiverFront Cottage>Private Pier>Firepit & Wildlife

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

Downtown Eastside gem near Fiserv Forum Water St Brady St
Downtown Milwaukee
9.0 out of 10, Wonderful, (64 reviews)
"Nice condo, very convenient."
United States
Mark W.
The price is NZ$588
includes taxes & fees
2 Oct - 3 Oct
Downtown Eastside gem near Fiserv Forum Water St Brady St

16. Sandy Toes at Lighthouse Cove

Sandy Toes at Lighthouse Cove
Lake Delton
9.8 out of 10, Exceptional, (35 reviews)
"Very nice condo, very clean and comfortable. Convenient to all atractions."
United States
Katherine A.
The price is NZ$337
includes taxes & fees
4 Oct - 5 Oct
Sandy Toes at Lighthouse Cove

17. 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, (95 reviews)
"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"
United States
nate k.
The price is NZ$369
includes taxes & fees
1 Nov - 2 Nov
Ohio Street Retreat-hot tub, pool, massage chair

18. 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 NZ$406
includes taxes & fees
5 Oct - 6 Oct
Piers & Pines at Island Pointe

19. Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
Ferryville
9.8 out of 10, Exceptional, (554 reviews)
"Loved the remoteness,singing of the birds and especially the hot tub was wonderful. now I can say I have stayed in a caboose. The countryside was great for taking a drive."
United States
Bruce R.
The price is NZ$427
includes taxes & fees
5 Oct - 6 Oct
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

20. 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, (111 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
The price is NZ$484
includes taxes & fees
4 Oct - 5 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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 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.

Explore a world of travel with Expedia