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Holiday Homes in Southern Wisconsin

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Check prices for these dates

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

Our top choices for Southern Wisconsin holiday homes

A field of lavender with a path leading through it.

1. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is NZ$209
includes taxes & fees
15 Oct - 16 Oct
Tamarack Point Homestead
A serene park with a pond, lush green grass, and a house in the background.

2. 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 NZ$299
includes taxes & fees
1 Nov - 2 Nov
Country home with flowing river
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

3. 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 NZ$370
includes taxes & fees
8 Nov - 9 Nov
Ohio Street Retreat-hot tub, pool, massage chair
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

4. The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
9.8 out of 10, Exceptional, (33 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is NZ$439
includes taxes & fees
18 Oct - 19 Oct
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

5. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (50 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is NZ$348
includes taxes & fees
27 Oct - 28 Oct
Gleason's Chouse
Living area

6. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (123 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is NZ$407
includes taxes & fees
19 Oct - 20 Oct
Serenity Cottage at Mineral Point
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

7. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (47 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is NZ$593
includes taxes & fees
18 Oct - 19 Oct
Updated home with lake views, across the street from Lake WI, near free ferry
Property grounds

8. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes
Necedah
10.0 out of 10, Exceptional, (39 reviews)
"This is a cute little place out in the country. Communication with the hostess was good."
United States
Dawn
The price is NZ$410
includes taxes & fees
15 Oct - 16 Oct
Remodeled, cozy, pet friendly cabin near lakes
A cabin with a deck, a covered porch, and a paved driveway.

9. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (71 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is NZ$485
includes taxes & fees
20 Oct - 21 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
A wooden deck with a bench, a white door, and hanging flower baskets.

10. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is NZ$287
includes taxes & fees
25 Oct - 26 Oct
The Bungaleau 1 Bedroom House In Cute Rivertown
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.

11. 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, (112 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$482
includes taxes & fees
18 Oct - 19 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

12. 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 NZ$301
includes taxes & fees
10 Nov - 11 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A house with a front porch, steps, and a small garden area.

13. Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.4 out of 10, Exceptional, (96 reviews)
"Comfy, cozy, and clean place to stay!!"
United States
Erin
The price is NZ$166
includes taxes & fees
11 Nov - 12 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A living room with a television, a coffee table, a sofa, and a dining area in the background.

14. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (31 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
The price is NZ$385
includes taxes & fees
26 Oct - 27 Oct
Hillsboro Driftless Guesthouse is cozy and ready for you!
A modern kitchen with white cabinetry, a wooden table, a wicker basket, and a hanging light fixture.

15. Carefully curated and walkable to all Princeton has to offer.

Carefully curated and walkable to all Princeton has to offer.
Princeton
10.0 out of 10, Exceptional, (8 reviews)
"Very clean and affordable. "
United States
Josh S.
The price is NZ$639
includes taxes & fees
9 Nov - 10 Nov
Carefully curated and walkable to all Princeton has to offer.
A single-story house with a front porch, a garage, and a small shed in a grassy yard surrounded by trees.

16. Fawn Lake Cottage for Families Looking for Privacy

Fawn Lake Cottage for Families Looking for Privacy
Wisconsin Dells
9.8 out of 10, Exceptional, (12 reviews)
"Great home and host beautiful home "
United States
Michael C.
The price is NZ$602
includes taxes & fees
15 Oct - 16 Oct
Fawn Lake Cottage for Families Looking for Privacy
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

17. Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Northside
9.8 out of 10, Exceptional, (69 reviews)
"I"
United States
Charlie
The price is NZ$314
includes taxes & fees
22 Oct - 23 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

18. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (64 reviews)
"Perfect place for a quick weekend getaway"
United States
Jack H.
The price is NZ$539
includes taxes & fees
25 Oct - 26 Oct
Riverfront Twin Home
A multi-story hotel with a pool area and a beach.

19. Dells Paradise At Lighthouse Cove Condominiums

Dells Paradise At Lighthouse Cove Condominiums
Lake Delton
9.6 out of 10, Exceptional, (20 reviews)
"My friends and I enjoyed our stay here. "
United States
Haily A.
The price is NZ$572
includes taxes & fees
21 Oct - 22 Oct
Dells Paradise At Lighthouse Cove Condominiums
A serene lakeside setting with a wooden dock extending into the water, surrounded by lush greenery and trees.

20. Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.8 out of 10, Exceptional, (64 reviews)
"The whole process from rental to leaving was simple. Loved the two docks available to fish from (front and rear of the cottage). Husband loved that there was kayaks , canoe l, and row boat available to get out on the lake. Home was very inviting and home like. Would definitely stay again!"
United States
Rebecca L.
The price is NZ$538
includes taxes & fees
18 Oct - 19 Oct
Lake Cottage 30 minutes from Wisconsin Dells.
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

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

10/10 Excellent
"The hotel was very good, the doorman and customer service at the desk were excellent. The hotel was very clean and we enjoyed our stay. I think the $36 for overnight parking was high, but other than that the stay was excellent. Everything we wanted to do (Pabst theatre, Usinger's sausage, riverwalk) was within walking distance,"
Joshua 1-night trip
Posted 6 hours ago
Hyatt Regency Milwaukee

Find out more about Southern Wisconsin

Southern Wisconsin Holiday Homes information

Number of reviews
1,206
Accommodation
684 Holiday Homes
Lowest Price
NZ$166
Highest Price
NZ$639

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