Southern Wisconsin Holiday Rentals

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Holiday Rentals in Southern Wisconsin

Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (2310)
"Great place to go with the little ones … "
The price is NZ$278
per night
24 Jun - 25 Jun
Timber Ridge Lodge and Waterpark
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (810)
"The two bedroom suite was affordable and wonderful for traveling with multiple family members."
The price is NZ$313
per night
23 Jun - 24 Jun
Grandstay Residential Suites Hotel - Sheboygan
The Plaza Hotel
3.0 star property
8.6 out of 10, Excellent, (986)
"The place was very clean, friendly staff and well kept up. It has a lot fo its original historic charm which I really liked."
The price is NZ$337
per night
2 Jun - 3 Jun
The Plaza Hotel
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*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
9.8 out of 10, Exceptional, (114)
"Cozy property with nice trail nearby. Walking distance to main street Dells."
The price is NZ$472
per night
2 Jun - 3 Jun
*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
Mill Creek Hotel
2.5 star property
9.2 out of 10, Wonderful, (1092)
"Would definitely go again "
The price is NZ$369
per night
2 Jun - 3 Jun
Mill Creek Hotel
Caribbean Club Resort
3.0 star property
8.0 out of 10, Very good, (315)
"Great resort , very clean and comfortable!"
Caribbean Club Resort
Bluegreen Vacations Odyssey Dells Resort
3.5 star property
9.2 out of 10, Wonderful, (76)
"The only thing I did not like was the pull-out couch-very uncomfortable and the ice machine was loud. "
Bluegreen Vacations Odyssey Dells Resort
Tamarack Wisconsin Dells a Ramada by Wyndham
3.0 star property
9.2 out of 10, Wonderful, (896)
"It was amazing just like being at home quiet east to find very well kept up"
Tamarack Wisconsin Dells a Ramada by Wyndham
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
9.8 out of 10, Exceptional, (181)
"This is the second time we stayed at The Retreat. LOTS of space inside and out for our family to gather. Kids age 3-10 could not get enough of the heated pool and the adults especially enjoyed the hot tub. We added an 'exrra' and had a small family reunion one of the afternoons and the place was perfect for this. Game room such a bonus when it rained. We didn't need to leave the property but some checked out 7 Mile Fair. Communication with the owner was timely. I'm sure the family will vote to...
The price is NZ$1,531
per night
30 Jun - 1 Jul
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
Amazing Five Bedroom Milwaukee Vacation Home!!
10.0 out of 10, Exceptional, (30)
"Huge pool and pool room, arcade, pool table, ping pong, what’s not to like…?"
Amazing Five Bedroom Milwaukee Vacation Home!!
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
9.8 out of 10, Exceptional, (30)
"Overall, the property was very nice, and was the perfect size to accommodate all of us that were staying. I loved the location as it was back in the woods, quite, semi-private, and offered plenty of land to enjoy a bonfire, and recreational activities with my friends and family. The booking and check-in process was very easy and the host was extremely responsive to emails/questions. The only issues we had were ants in the upstairs bathroom and the yard had not been mowed in quite some time, but...
The price is NZ$305
per night
5 Jun - 6 Jun
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
Kasa Westown Milwaukee
4.0 star property
9.0 out of 10, Wonderful, (45)
"Great location close to downtown "
The price is NZ$314
per night
1 Jul - 2 Jul
Kasa Westown Milwaukee
condo with hot tub, full kitchen, & fireplace
8.4 out of 10, Very good, (39)
"Very nice property. We had a fantastic stay."
condo with hot tub, full kitchen, & fireplace
Across the street from the beach. In the heart of Lake Geneva!
9.8 out of 10, Exceptional, (70)
"Cute little place with awesome views of the lake!!! All the amenities needed, very nicely decorated, and comfy beds! Personal parking spot a great plus! Some maintenance required though and a funny smell that was not pleasant to come back to. We had to buy a candle to drown out the smell and one family member with autoimmune health struggles had difficultly with this."
The price is NZ$1,376
per night
2 Jun - 3 Jun
Across the street from the beach. In the heart of Lake Geneva!
Sunset Cove 303 · Steph's Waterfront Retreat
10.0 out of 10, Exceptional, (30)
"Property was exactly as advertised! Beautiful view of the water front."
The price is NZ$393
per night
17 Jun - 18 Jun
Sunset Cove 303 · Steph's Waterfront Retreat
Wisconsin Dells Wilderness Resort with Water park! Available July 29-August 4th.
Wisconsin Dells Wilderness Resort with Water park! Available July 29-August 4th.
Glamping Loft Lake Geneva
9.8 out of 10, Exceptional, (19)
"This was such a great location and venue for my daughters Bachlorette Party! We could walk everywhere and the girls had a blast in their tents!"
The price is NZ$1,962
per night
2 Jun - 3 Jun
Glamping Loft Lake Geneva
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, (215)
"What a relaxing getaway for us who are busy raising three kids- 21,17 and 14. It’s been well over a decade since we did anything as husband and wife, without the kids. We grew up in Port Washington and savored being on Lake Michigan on two beautiful Spring Days. We took lots of walks and ate take out on the patio. With such views who needs a restaurant?? A total gem of a place, we will be back again. Thank you Mark!!"
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Wisconsin Dells Condo w/ Pool & Resort Amenities!
The price is NZ$609
per night
2 Jun - 3 Jun
Wisconsin Dells Condo w/ Pool & Resort Amenities!
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
9.0 out of 10, Wonderful, (83)
"We stayed two nights. The location is wonderful--right across from Lake Geneva. We would stay there again."
The price is NZ$537
per night
16 Jun - 17 Jun
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
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See all available properties in Southern Wisconsin
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.

Other types of properties in Southern Wisconsin you may be interested in

The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1644)
"Rooms are clean and updated. Wonderful view of the Capitol building. We walked to the Saturday am Farmers market. "
The price is NZ$342
per night
13 Jun - 14 Jun
The Madison Concourse Hotel and Governor's Club
Mt. Olympus Water & Theme Park Resort
3.0 star property
6.2 out of 10, (1851)
"The hotel internet did not work the whole time we were there. "They were fixing it every time I called". The water park and theme park were great though. Just need to update their hotels. "
The price is NZ$46
per night
2 Jun - 3 Jun
Mt. Olympus Water & Theme Park Resort
Saint Kate - The Arts Hotel
4.0 star property
9.8 out of 10, Exceptional, (1693)
"Everything was top tier!"
The price is NZ$337
per night
2 Jun - 3 Jun
Saint Kate - The Arts Hotel
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.

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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