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Southern Wisconsin Holiday Rentals

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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 Southern Wisconsin holiday rentals

Exterior

1. 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, (132 reviews)
"This is definitely a hidden gem and we will be back next year for some time away from the business of life."
United States
Melissa
The price is HK$860
HK$1,238 total
includes taxes & fees
8 Sept - 9 Sept
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
Property grounds

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 HK$715
HK$920 total
includes taxes & fees
31 Aug - 1 Sept
Tamarack Point Homestead
Interior

3. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"Absolutely wonderful as always will be back"
United States
Chad E.
The price is HK$1,317
HK$1,588 total
includes taxes & fees
1 Sept - 2 Sept
Your adventure begins the second you arrive!
Property grounds

4. 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 HK$745
HK$1,836 total
includes taxes & fees
31 Aug - 1 Sept
Remodeled, cozy, pet friendly cabin near lakes
Lobby

5. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,075 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$823
HK$934 total
includes taxes & fees
27 Sept - 28 Sept
Grandstay Residential Suites Hotel - Sheboygan
Terrace/patio

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 HK$981
HK$1,257 total
includes taxes & fees
31 Aug - 1 Sept
The Bungaleau 1 Bedroom House In Cute Rivertown
Reception

7. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (177 reviews)
"nice location"
United States
Mary
The price is HK$1,000
HK$1,155 total
includes taxes & fees
7 Sept - 8 Sept
The Dylin
Exterior

8. Country Living at its Finest

Country Living at its Finest
Viroqua
9.8 out of 10, Exceptional, (238 reviews)
"Great cabin -private but close enough to town and near many trout streams."
United States
jennifer g.
The price is HK$1,168
HK$1,737 total
includes taxes & fees
11 Sept - 12 Sept
Country Living at its Finest
Beach nearby

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (232 reviews)
"Great view and location "
United States
Matthew
The price is HK$545
HK$1,554 total
includes taxes & fees
2 Sept - 3 Sept
The Docksider - Couples & Young Families - Lakefront!
Property grounds

10. Piers & Pines at Island Pointe

Piers & Pines at Island Pointe
Wisconsin Dells
10.0 out of 10, Exceptional, (31 reviews)
"Clean, cozy and close to everything!"
United States
Richard R.
The price is HK$841
HK$1,939 total
includes taxes & fees
30 Sept - 1 Oct
Piers & Pines at Island Pointe
Property grounds

11. 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 HK$1,090
HK$1,315 total
includes taxes & fees
31 Aug - 1 Sept
Country home with flowing river
Smart TV

12. RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife
Princeton
10.0 out of 10, Exceptional, (44 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 HK$978
HK$2,082 total
includes taxes & fees
8 Sept - 9 Sept
RiverFront Cottage>Private Pier>Firepit & Wildlife
Property grounds

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, (66 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 HK$768
HK$1,334 total
includes taxes & fees
23 Sept - 24 Sept
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Coffee/tea maker, fridge, microwave, oven

14. 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 HK$1,101
HK$1,798 total
includes taxes & fees
3 Sept - 4 Sept
Ohio Street Retreat-hot tub, pool, massage chair
Children’s area

15. 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, (140 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is HK$1,129
HK$1,365 total
includes taxes & fees
1 Sept - 2 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

16. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (31 reviews)
"We had a great stay"
United States
Robert S.
The price is HK$1,411
HK$1,696 total
includes taxes & fees
31 Aug - 1 Sept
River Road Retreat
Beach nearby

17. Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic

Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic
Lake Delton
10.0 out of 10, Exceptional, (73 reviews)
"Chris was great to work with."
United States
Paul A.
The price is HK$814
HK$1,899 total
includes taxes & fees
14 Sept - 15 Sept
Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic
Smart TV, fireplace

18. 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 HK$1,270
HK$1,906 total
includes taxes & fees
28 Sept - 29 Sept
Serenity Cottage at Mineral Point
Smart TV, fireplace, books, stereo

19. Stylish 1 bedroom cottage along the Mississippi River

Stylish 1 bedroom cottage along the Mississippi River
Stoddard
9.6 out of 10, Exceptional, (32 reviews)
"Perfect for a weekend getaway! Super clean and had everything we needed. "
United States
Dean H.
The price is HK$1,058
HK$1,282 total
includes taxes & fees
1 Sept - 2 Sept
Stylish 1 bedroom cottage along the Mississippi River
Beach

20. Lake Geneva, Fireplace, Pool, Wifi, King Bed

Lake Geneva, Fireplace, Pool, Wifi, King Bed
Lake Geneva
10.0 out of 10, Exceptional, (45 reviews)
"Exactly as described — a clean, comfy condo near the lake! The fireplace was a great feature for a chilly spring visit!"
United States
Pamela P.
The price is HK$1,016
HK$2,355 total
includes taxes & fees
31 Aug - 1 Sept
Lake Geneva, Fireplace, Pool, Wifi, King Bed
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

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

10/10 Excellent
"Todo estuvo muy bien desde la llegada hasta al salir de la propiedad los servicios que solicité todo estaba bien gracias por su amabilidad y gracias a Expedia por hacer todo más fácil . Dios les bendiga."
Denis 1-night trip
Posted 2 hours ago
Mt. Olympus Water & Theme Park Resort

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