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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (1,111 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥18,994
￥21,559 total
includes taxes & fees
Nov 15 - Nov 16
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, (199 reviews)
"Good location"
United States
ANCA
The price is ￥17,040
￥19,681 total
includes taxes & fees
Nov 1 - Nov 2
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, (149 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
The price is ￥17,411
￥25,047 total
includes taxes & fees
Nov 19 - Nov 20
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, (3,489 reviews)
"Nice experience definitely recommend it"
United States
Kimberly
The price is ￥19,346
￥27,757 total
includes taxes & fees
Oct 29 - Oct 30
Timber Ridge Lodge and Waterpark
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

5. 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 ￥20,949
￥24,700 total
includes taxes & fees
Nov 2 - Nov 3
The Plaza Hotel
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

6. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (140 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 ￥26,354
￥39,266 total
includes taxes & fees
Oct 23 - Oct 24
A Comfy Cozy Cottage on Clowney
A beachside area with a sandy shore, a small dock, and several beach huts.

7. 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 ￥27,066
￥28,555 total
includes taxes & fees
Oct 24 - Oct 25
Tiki Beach Campground
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

8. 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 ￥22,159
￥26,717 total
includes taxes & fees
Nov 11 - Nov 12
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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 ￥11,008
￥31,371 total
includes taxes & fees
Oct 25 - Oct 26
The Docksider - Couples & Young Families - Lakefront!
Fire Pit

10. Top Floor Retreat at Delton Grand

Top Floor Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (44 reviews)
"Everything was good. Definitely would stay again. "
United States
Matt J.
The price is ￥14,586
￥37,942 total
includes taxes & fees
Oct 27 - Oct 28
Top Floor Retreat at Delton Grand
A waterfront hotel with multiple buildings, a dock, and a swimming pool.

11. 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 ￥11,533
￥32,165 total
includes taxes & fees
Oct 25 - Oct 26
Sandy Toes at Lighthouse Cove
A living room with a sofa, two armchairs, a coffee table, and a large window with a view of trees.

12. 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 ￥16,453
￥38,065 total
includes taxes & fees
Oct 25 - Oct 26
RiverFront Cottage>Private Pier>Firepit & Wildlife
A wooden cabin with a porch, two windows, and a star decoration on the wall.

13. 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 ￥28,490
￥34,399 total
includes taxes & fees
Oct 23 - Oct 24
River Road Retreat
A serene park with a pond, lush green grass, and a house in the background.

14. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (179 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is ￥22,001
￥26,552 total
includes taxes & fees
Nov 2 - Nov 3
Country home with flowing river
A waterfront hotel with multiple buildings, docked boats, and a surrounding forested area.

15. Dells Lakefront Escape - Couples or Families

Dells Lakefront Escape - Couples or Families
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"Good location, easy check in! The indoor pool was closed during our stay but we were notified in plenty of time and it was no big deal!"
United States
Tymica W.
The price is ￥14,226
￥35,513 total
includes taxes & fees
Oct 25 - Oct 26
Dells Lakefront Escape - Couples or Families
A lakeside view with a dock, picnic tables, and chairs.

16. 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 ￥14,513
￥36,014 total
includes taxes & fees
Oct 26 - Oct 27
Piers & Pines at Island Pointe
A two-story building with a balcony, labeled "Ole Bistro Inn" and "Vacation Rental."

17. 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 ￥22,001
￥28,565 total
includes taxes & fees
Nov 2 - Nov 3
Top location, no cleaning fee, everthings close B
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

18. 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 ￥18,831
￥33,972 total
includes taxes & fees
Nov 8 - Nov 9
Ohio Street Retreat-hot tub, pool, massage chair
A bathroom with a shower, toilet, and a towel rack.

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, (114 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 ￥30,865
￥42,983 total
includes taxes & fees
Oct 25 - Oct 26
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A beach with sun loungers and a view of a lake.

20. Beachtop Condo at Delton Grand - Waterfront

Beachtop Condo at Delton Grand - Waterfront
Lake Delton
10.0 out of 10, Exceptional, (41 reviews)
"Excellent communication and a wonderful place to stay. My family had a great time, and we would certainly consider returning in the future."
United States
Rishi
The price is ￥13,568
￥49,494 total
includes taxes & fees
Oct 22 - Oct 23
Beachtop Condo at Delton Grand - Waterfront
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

The Cove Of Lake Geneva

The Cove Of Lake Geneva

10/10 Excellent
"Just the right amount of space for the family. Nice to walk downtown."
Lisa 1-night trip
Posted 1 hour ago
The Cove Of Lake Geneva

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