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

Holiday Homes in Southwest Wisconsin

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Our top choices for Southwest Wisconsin holiday homes

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, (32 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 AU$304
includes taxes & fees
5 Nov - 6 Nov
Hillsboro Driftless Guesthouse is cozy and ready for you!

2. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (16 reviews)
"Sweet home! Loved all the bright colored decorations! We had a great stay here with our bikes and pups. The porch was lovely to watch a thunderstorm from as well!"
United States
Emily B.
The price is AU$356
includes taxes & fees
5 Nov - 6 Nov
Colorful getaway in friendly Driftless village

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, (99 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is AU$289
includes taxes & fees
8 Nov - 9 Nov
Ohio Street Retreat-hot tub, pool, massage chair

4. Downtown Spring Green Oasis | Hot Tub & Fire Pit

Downtown Spring Green Oasis | Hot Tub & Fire Pit
Spring Green
9.8 out of 10, Exceptional, (28 reviews)
"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."
United States
Elizabeth N.
The price is AU$438
includes taxes & fees
8 Nov - 9 Nov
Downtown Spring Green Oasis | Hot Tub & Fire Pit

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is AU$178
includes taxes & fees
24 Nov - 25 Nov
Tamarack Point Homestead

6. River Road Getaway

River Road Getaway
Muscoda
9.6 out of 10, Exceptional, (42 reviews)
"Had everything we needed."
United States
Tawnia
The price is AU$283
includes taxes & fees
5 Nov - 6 Nov
River Road Getaway

7. Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer
Baraboo
9.8 out of 10, Exceptional, (8 reviews)
"This unit was conveniently located, clean and well appointed. The host was friendly and helpful. Had a great time!"
United States
Gerard B.
The price is AU$434
includes taxes & fees
5 Nov - 6 Nov
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

8. 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, (34 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 AU$351
includes taxes & fees
21 Nov - 22 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

9. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (64 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 AU$357
includes taxes & fees
16 Nov - 17 Nov
The Honey Haven

10. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (126 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is AU$345
includes taxes & fees
1 Dec - 2 Dec
Serenity Cottage at Mineral Point

11. Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake
Baraboo
10.0 out of 10, Exceptional, (11 reviews)
"Excellent house and fun for the whole family! We can’t wait to stay again!"
United States
Cristin S.
The price is AU$927
includes taxes & fees
8 Nov - 9 Nov
Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

12. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (108 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AU$218
includes taxes & fees
5 Nov - 6 Nov
The Bungaleau 1 Bedroom House In Cute Rivertown

13. 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 AU$291
includes taxes & fees
17 Nov - 18 Nov
Remodeled, cozy, pet friendly cabin near lakes

14. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury
Lake Delton
9.6 out of 10, Exceptional, (15 reviews)
"Nice property and close to many of the Dells attractions."
United States
Mark V.
The price is AU$424
includes taxes & fees
5 Nov - 6 Nov
Dells Lake Villa - Lake Front Luxury

15. Elegant Lake Home with Hot Tub

Elegant Lake Home with Hot Tub
Tomah
9.8 out of 10, Exceptional, (38 reviews)
"We loved our stay here! We would definitely book this house again if we come back to the area."
United States
Delila M.
The price is AU$564
includes taxes & fees
11 Nov - 12 Nov
Elegant Lake Home with Hot Tub

16. 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, (54 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 AU$339
includes taxes & fees
5 Nov - 6 Nov
Hamilton Goebel House 816 E Louisa St Darlington Wi

17. 5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green
Lyndon Station
9.8 out of 10, Exceptional, (97 reviews)
"Had a great time with family for week vacation! The property was excellent and the hosts were very helpful and super kind!"
United States
Jaime T.
The price is AU$868
includes taxes & fees
11 Nov - 12 Nov
5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

18. 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 AU$468
includes taxes & fees
5 Nov - 6 Nov
Fawn Lake Cottage for Families Looking for Privacy

19. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome
Baraboo
10.0 out of 10, Exceptional, (50 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 AU$767
includes taxes & fees
2 Dec - 3 Dec
Draper Vacation Home - Families & Friends Welcome

20. HOT TUB and gorgeous lake views-The Lily Pad A Frame-minutes from Dells

HOT TUB and gorgeous lake views-The Lily Pad A Frame-minutes from Dells
Wisconsin Dells
10.0 out of 10, Exceptional, (21 reviews)
"This house was absolutely amazing and beautiful, featuring a truly great location that made exploring the area incredibly convenient. Furthermore, the property was impeccably clean, providing a welcoming, comfortable, and stress-free environment for the entire stay."
United States
Alaina R.
The price is AU$734
includes taxes & fees
29 Nov - 30 Nov
HOT TUB and gorgeous lake views-The Lily Pad A Frame-minutes from 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 Southwest Wisconsin Hotel Reviews

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Number of reviews
905
Accommodation
591 Holiday Homes
Lowest Price
AU$178
Highest Price
AU$927

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