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

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Our top choices for Southwest Wisconsin vacation 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 ¥21,395
¥33,607 total
includes taxes & fees
Nov 10 - Nov 11
Hillsboro Driftless Guesthouse is cozy and ready for you!

2. 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, (100 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is ¥18,827
¥32,198 total
includes taxes & fees
Nov 8 - Nov 9
Ohio Street Retreat-hot tub, pool, massage chair

3. 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 ¥28,526
¥32,770 total
includes taxes & fees
Nov 8 - Nov 9
River Road Getaway

4. Colorful getaway in friendly Driftless village

Colorful getaway in friendly Driftless village
Wonewoc
10.0 out of 10, Exceptional, (16 reviews)
"This is a cozy house with an excellent location, as we were biking and this is walking distance from the bike trail. We were a party of four and werenicely satisfied. We were very happy with communications!"
United States
Denise L.
The price is ¥31,498
¥39,379 total
includes taxes & fees
Dec 8 - Dec 9
Colorful getaway in friendly Driftless village

5. 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 ¥43,233
¥49,623 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Spring Green Oasis | Hot Tub & Fire Pit

6. 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 ¥24,105
¥49,126 total
includes taxes & fees
Nov 8 - Nov 9
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer

7. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is ¥16,640
¥19,562 total
includes taxes & fees
Nov 24 - Nov 25
Tamarack Point Homestead

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 ¥20,602
¥38,493 total
includes taxes & fees
Nov 21 - Nov 22
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

9. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is ¥20,175
¥36,137 total
includes taxes & fees
Nov 9 - Nov 10
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.

10. 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 ¥23,320
¥102,737 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Luxe Retreat| High-End Design w/outdoor fire pit WI Dells, Cascade MT, Devils Lake

11. 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 ¥26,625
¥39,627 total
includes taxes & fees
Dec 5 - Dec 6
The Honey Haven

12. 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 ¥28,526
¥38,176 total
includes taxes & fees
Dec 1 - Dec 2
Serenity Cottage at Mineral Point

13. 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 ¥17,544
¥49,164 total
includes taxes & fees
Nov 8 - Nov 9
Dells Lake Villa - Lake Front Luxury

14. 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 ¥12,346
¥32,086 total
includes taxes & fees
Nov 17 - Nov 18
Remodeled, cozy, pet friendly cabin near lakes

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.
Elegant Lake Home with Hot Tub

16. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (182 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is ¥21,891
¥25,090 total
includes taxes & fees
Nov 16 - Nov 17
Country home with flowing river

17. 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 ¥16,260
¥38,281 total
includes taxes & fees
Nov 9 - Nov 10
Hamilton Goebel House 816 E Louisa St Darlington Wi

18. 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 ¥49,755
¥93,456 total
includes taxes & fees
Nov 15 - Nov 16
5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green

19. 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 ¥18,384
¥50,655 total
includes taxes & fees
Nov 18 - Nov 19
Fawn Lake Cottage for Families Looking for Privacy

20. 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 ¥38,790
¥86,836 total
includes taxes & fees
Nov 30 - Dec 1
Draper Vacation Home - Families & Friends Welcome
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 Vacation Homes information

Number of reviews
777
Accommodation
498 Vacation Homes
Lowest Price
¥19,562
Highest Price
¥102,737

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