A lighthouse and a house with a red roof.

Southern Wisconsin Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Southern Wisconsin vacation 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, (1,108 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥18,963
￥21,523 total
includes taxes & fees
Nov 1 - Nov 2
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, (196 reviews)
"Good location"
United States
ANCA
The price is ￥15,251
￥17,614 total
includes taxes & fees
Nov 18 - Nov 19
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, (147 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
The price is ￥14,696
￥22,173 total
includes taxes & fees
Nov 16 - Nov 17
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

4. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,258 reviews)
"Parking was reasonable and close by"
United States
Danita
The price is ￥20,687
￥24,391 total
includes taxes & fees
Nov 2 - Nov 3
The Plaza Hotel
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

5. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,486 reviews)
"Nice experience definitely recommend it"
United States
Kimberly
The price is ￥19,074
￥27,436 total
includes taxes & fees
Nov 4 - Nov 5
Timber Ridge Lodge and Waterpark
A beachside area with a sandy shore, a small dock, and several beach huts.

6. Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
8.0 out of 10, Very good, (7 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 ￥27,022
￥28,508 total
includes taxes & fees
Oct 19 - Oct 20
Tiki Beach Campground
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

7. 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, (149 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥22,123
￥26,674 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A beach with sun loungers and a view of a lake.

8. 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 ￥14,203
￥37,403 total
includes taxes & fees
Nov 9 - Nov 10
Top Floor Retreat at Delton Grand
A lakeside view with beach chairs and a dock.

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (235 reviews)
"Amazing property right on the water, great location, fully recommend!"
United States
Ryan H.
The price is ￥10,990
￥31,319 total
includes taxes & fees
Oct 20 - Oct 21
The Docksider - Couples & Young Families - Lakefront!
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

10. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (139 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 ￥26,310
￥39,201 total
includes taxes & fees
Oct 19 - Oct 20
A Comfy Cozy Cottage on Clowney
A serene park with a pond, lush green grass, and a house in the background.

11. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (178 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is ￥21,965
￥26,508 total
includes taxes & fees
Nov 1 - Nov 2
Country home with flowing river
A two-story building with a balcony, labeled "Ole Bistro Inn" and "Vacation Rental."

12. Top location, no cleaning fee, everthings close B

Top location, no cleaning fee, everthings close B
Lake Geneva
10.0 out of 10, Exceptional, (79 reviews)
"Great location and cozy place!"
United States
Justin G.
The price is ￥21,965
￥28,518 total
includes taxes & fees
Nov 2 - Nov 3
Top location, no cleaning fee, everthings close B
A living room with a sofa, two armchairs, a coffee table, and a large window with a view of trees.

13. 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 ￥16,426
￥37,835 total
includes taxes & fees
Oct 19 - Oct 20
RiverFront Cottage>Private Pier>Firepit & Wildlife
A waterfront hotel with multiple buildings, a dock, and a swimming pool.

14. Sandy Toes at Lighthouse Cove

Sandy Toes at Lighthouse Cove
Lake Delton
9.8 out of 10, Exceptional, (36 reviews)
"Very nice condo, very clean and comfortable. Convenient to all atractions."
United States
Katherine A.
The price is ￥10,652
￥30,939 total
includes taxes & fees
Oct 20 - Oct 21
Sandy Toes at Lighthouse Cove
A modern urban street with multi-story buildings, a traffic light, and a crosswalk.

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, (66 reviews)
"Nice condo, very convenient."
United States
Mark W.
The price is ￥35,555
￥50,676 total
includes taxes & fees
Oct 25 - Oct 26
Downtown Eastside gem near Fiserv Forum Water St Brady St
A wooden cabin with a porch, two windows, and a star decoration on the wall.

16. 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 ￥28,444
￥34,343 total
includes taxes & fees
Oct 22 - Oct 23
River Road Retreat
A lakeside view with a dock, picnic tables, and chairs.

17. 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 ￥13,982
￥35,210 total
includes taxes & fees
Oct 19 - Oct 20
Piers & Pines at Island Pointe
A field of lavender with a path leading through it.

18. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (47 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is ￥14,411
￥18,538 total
includes taxes & fees
Oct 19 - Oct 20
Tamarack Point Homestead
A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

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, (113 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 ￥30,814
￥43,432 total
includes taxes & fees
Oct 19 - Oct 20
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

20. 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)
"Nice stay, will stay again."
United States
Thomas D.
The price is ￥18,773
￥33,867 total
includes taxes & fees
Nov 1 - Nov 2
Ohio Street Retreat-hot tub, pool, massage chair
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

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"Pretty fast check in breakfast very good staff is very nice people"
Nelson 1-night trip
Posted 6 hours ago
Drury Plaza Hotel Milwaukee Downtown

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