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

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Southwest Wisconsin vacation homes

Smart TV, DVD player

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)
"Nice place just outside city limits. Good spot to check out the area."
United States
Dan G.
The price is AED 473
AED 789 total
includes taxes & fees
23 Sep - 24 Sep
Hillsboro Driftless Guesthouse is cozy and ready for you!
Exterior

2. 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 AED 735
AED 961 total
includes taxes & fees
23 Sep - 24 Sep
Colorful getaway in friendly Driftless village
Interior

3. The Honey Haven

The Honey Haven
Westby
10.0 out of 10, Exceptional, (61 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 AED 588
AED 926 total
includes taxes & fees
23 Sep - 24 Sep
The Honey Haven
Smart TV, fireplace

4. 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 AED 565
AED 856 total
includes taxes & fees
28 Sep - 29 Sep
Serenity Cottage at Mineral Point
Property grounds

5. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveler
The price is AED 335
AED 431 total
includes taxes & fees
23 Sep - 24 Sep
Tamarack Point Homestead
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, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is AED 459
AED 589 total
includes taxes & fees
23 Sep - 24 Sep
The Bungaleau 1 Bedroom House In Cute Rivertown
Coffee/tea maker, fridge, microwave, oven

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, (93 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 AED 516
AED 883 total
includes taxes & fees
27 Sep - 28 Sep
Ohio Street Retreat-hot tub, pool, massage chair
Exterior

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

Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Ontario
10.0 out of 10, Exceptional, (11 reviews)
"Really nice quiet place. Perfect for our hunting trip. "
United States
Kolin C.
The price is AED 639
AED 1,325 total
includes taxes & fees
29 Sep - 30 Sep
Cozy, quiet Cabin near Kickapoo River & Wildcat Mountain. Perfect for fisherman.
Outdoor dining

9. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (62 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 AED 496
AED 1,119 total
includes taxes & fees
23 Sep - 24 Sep
Riverfront Twin Home
Living area

10. 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, (7 reviews)
"Up for 9 day hunt and visiting family and friends. Jay was very friendly and answered all requests. Location was very good for what we needed for our visit. Inside was well kept."
United States
Roger S.
The price is AED 493
AED 1,064 total
includes taxes & fees
23 Sep - 24 Sep
Large 2-bedroom lower unit with fast WI-FI & in unit washer/dryer
Interior

11. 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, (111 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
The price is AED 716
AED 1,010 total
includes taxes & fees
23 Sep - 24 Sep
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Exterior

12. 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, (93 reviews)
"Very clean, private, enjoyable place with gracious hosts!"
United States
Caleb H.
5-Acre Luxury Chalet Near Wisconsin Dells Indoor/Outdoor Spa Suite Putting Green
Game room

13. 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 AED 393
AED 1,247 total
includes taxes & fees
23 Sep - 24 Sep
Fawn Lake Cottage for Families Looking for Privacy
Property grounds

14. 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 AED 441
AED 1,197 total
includes taxes & fees
24 Sep - 25 Sep
Lake Cottage 30 minutes from Wisconsin Dells.
Outdoor dining

15. 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, (20 reviews)
"We loved everything about this place."
United States
Jessabelle
The price is AED 514
AED 1,438 total
includes taxes & fees
23 Sep - 24 Sep
Charming 3-bedroom house with WiFi, AC in serene Necedah
TV, table tennis

16. Draper Vacation Home - Families & Friends Welcome

Draper Vacation Home - Families & Friends Welcome
Baraboo
10.0 out of 10, Exceptional, (49 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 AED 680
AED 1,835 total
includes taxes & fees
30 Sep - 1 Oct
Draper Vacation Home - Families & Friends Welcome
Property grounds

17. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes
Necedah
10.0 out of 10, Exceptional, (38 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 AED 349
AED 860 total
includes taxes & fees
28 Sep - 29 Sep
Remodeled, cozy, pet friendly cabin near lakes
Indoor pool, a heated pool

18. Making Memories Lodge @ Spring Brook Resort

Making Memories Lodge @ Spring Brook Resort
Spring Brook
9.8 out of 10, Exceptional, (60 reviews)
"Great with lots of space for a group. Enjoyed our stay"
United States
bev e.
The price is AED 1,062
AED 2,305 total
includes taxes & fees
5 Oct - 6 Oct
Making Memories Lodge @ Spring Brook Resort
Interior

19. 1950s Charm | Walk to UW-La Crosse

1950s Charm | Walk to UW-La Crosse
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (43 reviews)
"Walkable to grocery store, gas station and Restraunts which was super helpful since the rental car company was closed when we arrived at the airport due to our flight being delayed.Would definitely stay again"
United States
Kim M.
The price is AED 551
AED 1,639 total
includes taxes & fees
23 Sep - 24 Sep
1950s Charm | Walk to UW-La Crosse
Property grounds

20. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (176 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
Country home with flowing 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

Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

8/10 Good
"Staff was amazing and very family friendly! Not too great activity happening throughout the hotel crowd wise. Room had a strong mildew scent. Other than that pool was great for the kids and breakfast was nice!"
Anna 2-night trip
Posted 4 hours ago
Baymont by Wyndham Madison West/Middleton WI West

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