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

Southwest Wisconsin Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southwest Wisconsin vacation rentals

A wooden cabin with a porch, two windows, and a star decoration on the wall.

1. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
The price is ￥28,327
￥34,202 total
includes taxes & fees
Oct 1 - Oct 2
River Road Retreat
A cabin with a dining area, a bicycle, and a sign reading "Vangelis".

2. 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, (144 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
The price is ￥17,311
￥24,904 total
includes taxes & fees
Oct 29 - Oct 30
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
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)
"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 ￥31,474
￥41,673 total
includes taxes & fees
Oct 1 - Oct 2
Colorful getaway in friendly Driftless village
A living room with a television, a coffee table, a sofa, and a dining area in the background.

4. 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)
"Nice place just outside city limits. Good spot to check out the area."
United States
Dan G.
The price is ￥20,254
￥33,821 total
includes taxes & fees
Oct 7 - Oct 8
Hillsboro Driftless Guesthouse is cozy and ready for you!
A wooden deck leading to a white door with a sign reading "SIENNA SUNSET CHASER A PETITE RETREAT."

5. Yukon Trails RV & Camping Resort

Yukon Trails RV & Camping Resort
2.0 star property
Lyndon Station
9.0 out of 10, Wonderful, (6 reviews)
"My family and I love this place. This was our second time at Yukon Trails. We will be back for sure. "
United States
Alessandra
The price is ￥33,205
￥35,032 total
includes taxes & fees
Oct 4 - Oct 5
Yukon Trails RV & Camping Resort
Two white hammocks hanging on a wooden porch with a view of a garden.

6. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (85 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is ￥23,763
￥52,466 total
includes taxes & fees
Oct 25 - Oct 26
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

7. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"A great place to get away and relax."
United States
Betsy D.
The price is ￥27,697
￥33,372 total
includes taxes & fees
Oct 6 - Oct 7
Your adventure begins the second you arrive!
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

8. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (138 reviews)
"The cottage was very quaint and comfortable. Great location for exploring downtown Mineral Point on foot. Had a fun stay."
United States
Rick C.
The price is ￥26,202
￥39,040 total
includes taxes & fees
Oct 4 - Oct 5
A Comfy Cozy Cottage on Clowney
A wooden cabin surrounded by snow-covered trees.

9. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (53 reviews)
"Fun little place. Perfect for me and the wife. Close to Kickapoo area hiking. Hot tub was a nice touch to the neat little stay."
United States
Joel M.
The price is ￥25,966
￥51,737 total
includes taxes & fees
Oct 27 - Oct 28
Cabin on the Kickapoo
Living area

10. 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 ￥24,219
￥36,676 total
includes taxes & fees
Oct 5 - Oct 6
Serenity Cottage at Mineral Point
A rural landscape with a wooden fence, a field of crops, and distant buildings including a silo and a house.

11. Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Sparta
10.0 out of 10, Exceptional, (159 reviews)
"Loved the view and the peaceful setting! Very comfortable apartment, everything we needed and more. Perfect stay!"
United States
Nancy
The price is ￥23,936
￥28,906 total
includes taxes & fees
Oct 1 - Oct 2
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
A log cabin with a large porch, multiple windows, and a stone pathway leading to the entrance.

12. Rustic Hideaway Sleeps 4 HOT TUB

Rustic Hideaway Sleeps 4 HOT TUB
De Soto
10.0 out of 10, Exceptional, (53 reviews)
"A beautiful, well-kept cabin with plenty of amenities and meticulous surroundings... perfect for a quiet retreat. The owner was prompt in communicating when we had a couple of questions - very kind and friendly. Would definitely stay here again!!"
United States
Susan
The price is ￥33,284
￥63,804 total
includes taxes & fees
Oct 7 - Oct 8
Rustic Hideaway Sleeps 4 HOT TUB
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

13. 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, (94 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 ￥22,095
￥37,841 total
includes taxes & fees
Oct 5 - Oct 6
Ohio Street Retreat-hot tub, pool, massage chair
A wooden deck with a bench, a white door, and hanging flower baskets.

14. 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 ￥19,687
￥25,234 total
includes taxes & fees
Oct 4 - Oct 5
The Bungaleau 1 Bedroom House In Cute Rivertown
A compact kitchen with a built-in stove, a microwave, and a large TV.

15. Arrowhead Resort Campground

Arrowhead Resort Campground
2.0 star property
Wisconsin Dells
7.8 out of 10, Good, (47 reviews)
"Clean, well maintained cottage. Comfy beds. Super close to downtown activities."
United States
Alexis
The price is ￥19,671
￥20,754 total
includes taxes & fees
Oct 4 - Oct 5
Arrowhead Resort Campground
A dining area with a wooden table and chairs, a window with a view of trees, and a wall-mounted artwork of a chef.

16. Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
Lyndon Station
9.8 out of 10, Exceptional, (42 reviews)
"Very clean property and nice stay. "
United States
Arthur A.
The price is ￥30,451
￥60,184 total
includes taxes & fees
Oct 1 - Oct 2
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
A lakeside view with beach chairs and a dock.

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (235 reviews)
"The Lake Delton Docksider condo was clean, comfortable, and located close to all Wisconsin Dells attractions. We enjoyed sitting on the balcony and watching the boats pass by. Communication with the property manager was great and we had no issues."
United States
Tom T.
The price is ￥10,945
￥31,191 total
includes taxes & fees
Oct 4 - Oct 5
The Docksider - Couples & Young Families - Lakefront!
A bedroom with a bunk bed, a single bed, a ceiling fan, and a window with blinds.

18. Peyton's Place at Tamarack - Great Location!

Peyton's Place at Tamarack - Great Location!
Wisconsin Dells
10.0 out of 10, Exceptional, (30 reviews)
"The amenities are good, beds are comfortable and we would love to revisit again"
United States
Joyce W.
The price is ￥15,159
￥49,529 total
includes taxes & fees
Oct 1 - Oct 2
Peyton's Place at Tamarack - Great Location!
A wooden cabin with a porch, a picnic table, and a mailbox.

19. Quiet And Beautiful!!

Quiet And Beautiful!!
Warrens
9.2 out of 10, Wonderful, (204 reviews)
"Great place to stay comfortable and easy to access"
United States
Matthew
The price is ￥27,540
￥52,134 total
includes taxes & fees
Oct 1 - Oct 2
Quiet And Beautiful!!
A cozy log cabin interior with a fireplace, a sofa, and a large window offering a view of the outdoors.

20. Tiny House on the River

Tiny House on the River
Black River Falls
10.0 out of 10, Exceptional, (110 reviews)
"We loved staying at Tiny! We had everything we needed for a fun weekend away. There great communication from the hosts and they even left booklets about things to do in the area. Would definitely recommend!"
United States
Taylor V.
The price is ￥22,032
￥37,868 total
includes taxes & fees
Oct 7 - Oct 8
Tiny House on the River
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

Best Western Baraboo Inn

Best Western Baraboo Inn

8/10 Good
"Clean, good location for me."
Nathan 1-night trip
Posted 14 hours ago
Best Western Baraboo Inn

Find out more about Southwest Wisconsin

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