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

Southwest Wisconsin Holiday Rentals

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Our top choices for Southwest Wisconsin holiday rentals

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, (161 reviews)
"Great place to spend outdoors, staff are friendly and always there if anything is needed."
United States
Brenda
The price is NZ$249
includes taxes & fees
10 Dec - 11 Dec
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

2. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (216 reviews)
"Good location"
United States
ANCA
The price is NZ$226
includes taxes & fees
19 Nov - 20 Nov
The Dylin

3. 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 NZ$361
includes taxes & fees
15 Nov - 16 Nov
River Road Retreat

4. Crooked Creek - Relaxation Cabin

Crooked Creek - Relaxation Cabin
Boscobel
9.8 out of 10, Exceptional, (13 reviews)
"Nice location quiet and relaxing)."
United States
Nick N.
The price is NZ$265
includes taxes & fees
15 Nov - 16 Nov
Crooked Creek - Relaxation Cabin

5. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (142 reviews)
"This is such a charming and unique old place, and right next to downtown. What a perfect location in one of the most charming and welcoming towns you'll ever visit!"
United States
Cindy P.
The price is NZ$399
includes taxes & fees
15 Nov - 16 Nov
A Comfy Cozy Cottage on Clowney

6. Crooked Creek - Serenity Cabin

Crooked Creek - Serenity Cabin
Boscobel
10.0 out of 10, Exceptional, (16 reviews)
"Worked well for our 2-day stay. "
United States
John V.
The price is NZ$323
includes taxes & fees
12 Nov - 13 Nov
Crooked Creek - Serenity Cabin

7. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (55 reviews)
"This is a beautiful place to spend a couple of relaxing days. "
United States
Sujhey B.
The price is NZ$480
includes taxes & fees
24 Nov - 25 Nov
Cabin on the Kickapoo

8. 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, (33 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 NZ$371
includes taxes & fees
12 Nov - 13 Nov
Hillsboro Driftless Guesthouse is cozy and ready for you!

9. Top Floor Retreat at Delton Grand

Top Floor Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (45 reviews)
"Our stay at Delton Grand top floor was perfect. The view of lake Delton was amazing. The facilities were excellent and we would definitely book again."
United States
Kenneth
The price is NZ$371
includes taxes & fees
12 Nov - 13 Nov
Top Floor Retreat at Delton Grand

10. Comfy Views Condo - Delton Grand 423

Comfy Views Condo - Delton Grand 423
Lake Delton
9.8 out of 10, Exceptional, (35 reviews)
"Christopher the host was out of this world great, he answered all my sometimes borderline silly questions very quickly, the place is beautiful and super clean, and a perfect location! Thanks so much for letting us stay in your awesome condo."
United States
Jon
The price is NZ$355
includes taxes & fees
12 Nov - 13 Nov
Comfy Views Condo - Delton Grand 423

11. Luxury Beachfront Retreat at Delton Grand

Luxury Beachfront Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (24 reviews)
"Perfect Lakeview!"
United States
Jacob
The price is NZ$350
includes taxes & fees
12 Nov - 13 Nov
Luxury Beachfront Retreat at Delton Grand

12. 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 NZ$353
includes taxes & fees
15 Nov - 16 Nov
Ohio Street Retreat-hot tub, pool, massage chair

13. Piers & Pines at Island Pointe

Piers & Pines at Island Pointe
Wisconsin Dells
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful stay. Perfect little cabin and hosts were very helpful."
United States
Alisia
The price is NZ$372
includes taxes & fees
12 Nov - 13 Nov
Piers & Pines at Island Pointe

14. Sandy Toes at Lighthouse Cove

Sandy Toes at Lighthouse Cove
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"Very clean and great location!"
United States
kristen g.
The price is NZ$332
includes taxes & fees
12 Nov - 13 Nov
Sandy Toes at Lighthouse Cove

15. 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, (91 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
The price is NZ$536
includes taxes & fees
15 Nov - 16 Nov
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

16. Sunset Studio, Amazing River Views, HOT TUB! New Listing!

Sunset Studio, Amazing River Views, HOT TUB! New Listing!
Eastman
9.4 out of 10, Exceptional, (22 reviews)
"Loved it will be back!"
United States
Nick C.
The price is NZ$493
includes taxes & fees
15 Nov - 16 Nov
Sunset Studio, Amazing River Views, HOT TUB! New Listing!

17. Stylish 1 bedroom cottage along the Mississippi River

Stylish 1 bedroom cottage along the Mississippi River
Stoddard
9.6 out of 10, Exceptional, (39 reviews)
"Very nice and clean property. Private location."
United States
Kevin
The price is NZ$275
includes taxes & fees
12 Nov - 13 Nov
Stylish 1 bedroom cottage along the Mississippi River

18. Dells Lakefront Escape - Couples or Families

Dells Lakefront Escape - Couples or Families
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"Good location, easy check in! The indoor pool was closed during our stay but we were notified in plenty of time and it was no big deal!"
United States
Tymica W.
The price is NZ$332
includes taxes & fees
12 Nov - 13 Nov
Dells Lakefront Escape - Couples or Families

19. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is NZ$219
includes taxes & fees
30 Nov - 1 Dec
Tamarack Point Homestead

20. 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 NZ$435
includes taxes & fees
1 Dec - 2 Dec
Serenity Cottage at Mineral Point
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southwest Wisconsin holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southwest Wisconsin. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southwest Wisconsin. Seeing all the best attractions is bound to make you fall in love with Southwest Wisconsin. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southwest Wisconsin short-term rentals, that won’t be hard to do.

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