A lake surrounded by lush green hills and a rocky cliff.

Holiday Homes in Southwest Wisconsin

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southwest Wisconsin holiday homes

A living room with a television, a coffee table, a sofa, and a dining area in the background.

1. 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, (29 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
The price is €189
includes taxes & fees
31 Aug - 1 Sept
Hillsboro Driftless Guesthouse is cozy and ready for you!
A field of lavender with a path leading through it.

2. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (42 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is €105
includes taxes & fees
31 Aug - 1 Sept
Tamarack Point Homestead
A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

3. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (15 reviews)
"It’s a cozy place with all cooking utensils you will ever need! Very comfy beds as well. "
United States
Randy R.
The price is €227
includes taxes & fees
31 Aug - 1 Sept
Colorful getaway in friendly Driftless village
A modern living room with a staircase, a dark door, a grey armchair, and a coffee table with decorative items.

4. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (58 reviews)
"This was my second time staying at the Honey Haven and I would love to stay again. The host does a wonderful job keeping the property in great shape and the area that the property is in is so special."
United States
Eric R.
The price is €222
includes taxes & fees
2 Sept - 3 Sept
The Honey Haven

5. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes
Necedah
10.0 out of 10, Exceptional, (37 reviews)
"This property was perfect. It was very clean and they had a lot of supplies available. The owner was very kind and very responsive. I would definitely recommend this place!"
United States
Rebekah
The price is €206
includes taxes & fees
31 Aug - 1 Sept
Remodeled, cozy, pet friendly cabin near lakes
A wooden deck with a bench, a white door, and hanging flower baskets.

6. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (101 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is €142
includes taxes & fees
30 Aug - 31 Aug
The Bungaleau 1 Bedroom House In Cute Rivertown
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

7. 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, (91 reviews)
"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"
United States
nate k.
The price is €193
includes taxes & fees
30 Aug - 31 Aug
Ohio Street Retreat-hot tub, pool, massage chair

8. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (122 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is €206
includes taxes & fees
28 Sept - 29 Sept
Serenity Cottage at Mineral Point
A bedroom with a bed, a ceiling fan, a nightstand, and a window with curtains.

9. Fawn Lake Cottage for Families Looking for Privacy

Fawn Lake Cottage for Families Looking for Privacy
Wisconsin Dells
9.8 out of 10, Exceptional, (11 reviews)
"Great home and host beautiful home "
United States
Michael C.
The price is €296
includes taxes & fees
30 Aug - 31 Aug
Fawn Lake Cottage for Families Looking for Privacy
A wooden deck with two wicker chairs and a small table, overlooking a grassy yard with trees and a white picket fence.

10. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome
Baraboo
10.0 out of 10, Exceptional, (47 reviews)
"It was a great place to rent for a weekend with the family. We were able to bring our dog too so that was amazing. The house was clean and it had everything you needed for toiletries, kitchen, board games, grill etc."
United States
Michele T.
The price is €396
includes taxes & fees
1 Sept - 2 Sept
Draper Vacation Home - Families & Friends Welcome
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

11. Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (51 reviews)
"Three couples stayed at this property. Very comfy beds. We all enjoyed our stay and already have plans to stay again in the fall. It is also close to the trails."
United States
Danette M.
The price is €196
includes taxes & fees
31 Aug - 1 Sept
Hamilton Goebel House 816 E Louisa St Darlington Wi
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

12. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (59 reviews)
"Great property! Enjoyed the property and outdoor space was amazing! While there is not conventional central air, the space stayed cool."
United States
Melissa
The price is €266
includes taxes & fees
30 Aug - 31 Aug
Riverfront Twin Home
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

13. 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, (65 reviews)
"This place has so much personality and charm! We loved our stay, so many fun little details to enjoy. Very easily accessible to the downtown area, which made our experience very smooth. We'd love to stay there again the next time we're in La Crosse."
United States
Colin W.
The price is €143
includes taxes & fees
31 Aug - 1 Sept
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A two-story house with a balcony, surrounded by a forest.

14. Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
9.8 out of 10, Exceptional, (10 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is €284
includes taxes & fees
22 Sept - 23 Sept
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
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.

15. 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, (110 reviews)
"Best location and fabulous hospitality!"
United States
Anne B.
The price is €229
includes taxes & fees
30 Aug - 31 Aug
MJ's Penthouse ,a piece of paradise on Monroe's historic square

16. 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 €299
includes taxes & fees
8 Sept - 9 Sept
Dells Paradise At Lighthouse Cove Condominiums
A serene park with a pond, lush green grass, and a house in the background.

17. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (174 reviews)
"Staying at this house was like staying at my grandmother’s house when I was a child. It was a wonderful experience, and the grounds were phenomenal."
United States
Jeff
The price is €148
includes taxes & fees
30 Aug - 31 Aug
Country home with flowing river
A serene lakeside setting with a wooden dock extending into the water, surrounded by lush greenery and trees.

18. Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.8 out of 10, Exceptional, (61 reviews)
"Very nice place to stay we had everything that we needed. Very clean and great owners"
United States
Margie O.
The price is €280
includes taxes & fees
10 Sept - 11 Sept
Lake Cottage 30 minutes from Wisconsin Dells.
A wooden deck with a table and chairs, surrounded by a wooden fence, overlooking a grassy area with trees.

19. Charming 3-bedroom house with WiFi, AC in serene Necedah

Charming 3-bedroom house with WiFi, AC in serene Necedah
Necedah
9.8 out of 10, Exceptional, (18 reviews)
"We loved everything about this place."
United States
Jessabelle
The price is €336
includes taxes & fees
30 Aug - 31 Aug
Charming 3-bedroom house with WiFi, AC in serene Necedah
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 Southwest Wisconsin Hotel Reviews

Sleep Inn & Suites Wisconsin Dells - Lake Delton

Sleep Inn & Suites Wisconsin Dells - Lake Delton

10/10 Excellent
"Wasn't able to use pool, but looked quite nice. Workout rm would be wonderful."
Theresa 2-night trip
Posted less than an hour ago
Sleep Inn & Suites Wisconsin Dells - Lake Delton

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Number of reviews
1,028
Accommodation
602 Holiday Homes
Lowest Price
€105
Highest Price
€396

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