Holiday Homes in Southwest Wisconsin

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Featured Holiday Homes in Southwest Wisconsin and around

Our top choices for Southwest Wisconsin holiday homes

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (968)
"The birch colony is great! It’s like its own apt! I like that it’s super convenient and not bothering others much! It’s also very close to Walmart!"
Tamarack Wisconsin Dells a Ramada by Wyndham

Newer Home Near Castle Rock Lake in New Lisbon, WI

10.0 out of 10, Exceptional, (13)
"Enjoyed our stay. Plenty of room for our mutual-generational family. The home was very clean and lived up to the pictures and description. Would certainly recommend! "
Newer Home Near Castle Rock Lake in New Lisbon, WI

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (141)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Eagles Nest Retreat! Private Decks In Town

9.8 out of 10, Exceptional, (169)
"This was a cozy cabin that slept 9 for us with a great location. Everything was very clean, great decks, and great communication with owners."
The price is €437
includes taxes & fees
2 Sept - 3 Sept
Eagles Nest Retreat! Private Decks In Town

Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

2.0 star property
10.0 out of 10, Exceptional, (18)
"The place was clean, and my family had a wonderful time during our stay."
The price is €866
includes taxes & fees
10 Sept - 11 Sept
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (56)
"The property and house are breathtaking. We particularly loved the Tea House. Gorgeous, clean and the host was wonderful and responsive. A great place to stay!"
Elegant country retreat near Spring Green w expansive views of Driftless Region

Red Oak Lodge @ Spring Brook Resort

9.6 out of 10, Exceptional, (45)
"This was a great place for a family holiday weekend. All 12 people had a great time and we left with many happy memories."
The price is €877
includes taxes & fees
2 Sept - 3 Sept
Red Oak Lodge @ Spring Brook Resort

Beach Lake Retreat with Private Lake and Hot Tub

10.0 out of 10, Exceptional, (35)
"Had an amazing time at this beautiful house."
Beach Lake Retreat with Private Lake and Hot Tub

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (64)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Dogwood Dream @ Spring Brook Resort

9.8 out of 10, Exceptional, (38)
"We were very happy with the house we rented. If was perfect for our family of 9. House had everything we needed. We would rent it again."
The price is €551
includes taxes & fees
2 Sept - 3 Sept
Dogwood Dream @ Spring Brook Resort

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (24)
"Prefect"
Paoli Den - Newly Remodeled!

Dog-friendly log cabin on the river with deck & firepit - near Wisconsin Dells

8.2 out of 10, Very good, (26)
"The cabin was clean, cozy and beautiful. We really enjoyed our stay."
Dog-friendly log cabin on the river with deck & firepit - near Wisconsin Dells

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (149)
"Enjoyed our stay. House worked out great- the number of beds/bedrooms and having 2 bathrooms was wonderful. Close to the downtown- easy 30 minute walk."
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Kokomo Cabin: Campfires, Family Fun & Pickleball

10.0 out of 10, Exceptional, (31)
"Perfect for me and my friends for a golf and casino weekend. The family visited from a couple miles away and really enjoyed the yard games and the beach. Kayaks and fishing were great for the kids. Plenty of room for all four couples, everyone had their own space. Firewood was provided, fantastic views for the fires at night. What a gorgeous home, we will be back! "
Kokomo Cabin: Campfires, Family Fun & Pickleball

Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court

2.0 star property
9.8 out of 10, Exceptional, (20)
"The Downtowner is clean & spacious in a quiet neighborhood. It is perfect for a family with young kids. The kids especially enjoyed the game room. We would stay here again! "
The price is €590
includes taxes & fees
1 Sept - 2 Sept
Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court

Spacious water front property located on Big Green Lake

9.6 out of 10, Exceptional, (52)
"This place was amazing and was perfect for out annual trip. "
Spacious water front property located on Big Green Lake

Last minute SALE 8/24-8/28!

9.8 out of 10, Exceptional, (88)
"Amazing! "
Last minute SALE 8/24-8/28!

Castle Rock Retreat - Peaceful Escape but close to the fun!

Castle Rock Retreat - Peaceful Escape but close to the fun!

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

Lake Arrowhead lakefront (4 bedroom and Game Room)

10.0 out of 10, Exceptional, (34)
"Property was easy to find and centrally located around all the wonderful golf courses in the area. Being on the water was also a huge plus. Plenty of things to do at the house both inside and out. We will be back!"
Lake Arrowhead lakefront (4 bedroom and Game Room)
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

Find out more about Southwest Wisconsin

Southwest Wisconsin Holiday Homes information

Number of reviews
Accommodation
651 Holiday Homes
Lowest Price
€437
Highest Price
€877

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