A lighthouse and a house with a red roof.

Southern Wisconsin Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southern Wisconsin holiday rentals

A spacious living area with a fireplace, a sofa, and a dining area in the background.

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 S$174
includes taxes & fees
1 Nov - 2 Nov
Grandstay Residential Suites Hotel - Sheboygan
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

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 S$165
includes taxes & fees
1 Nov - 2 Nov
The Dylin
A cabin with a dining area, a bicycle, and a sign reading "Vangelis".

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 S$190
includes taxes & fees
1 Nov - 2 Nov
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

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 S$214
includes taxes & fees
21 Oct - 22 Oct
Timber Ridge Lodge and Waterpark
An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

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 S$270
includes taxes & fees
1 Nov - 2 Nov
Mill Creek Hotel
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

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 S$262
includes taxes & fees
21 Oct - 22 Oct
The Plaza Hotel
A compact kitchen with a built-in stove, a microwave, and a large TV.

7. 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 S$169
includes taxes & fees
4 Oct - 5 Oct
Arrowhead Resort Campground
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

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

10/10 Excellent
"Room was great and staff was very friendly"
Anthony 1-night trip
Posted 2 hours ago
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

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