Holiday Homes in Southwest Wisconsin

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Holiday Homes in Southwest Wisconsin

Our top choices for Southwest Wisconsin holiday homes

Tamarack Wisconsin Dells a Ramada by Wyndham
Indoor pool, seasonal outdoor pool

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (967)
"Was in great shape "
Tamarack Wisconsin Dells a Ramada by Wyndham
Newer Home Near Castle Rock Lake in New Lisbon, WI
TV, DVD player, table football, ping pong

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
Exterior

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
Exterior

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 AU$771
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+!
Fridge, microwave, oven, stovetop

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 AU$1,525
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
Smart TV, DVD player, books

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

10.0 out of 10, Exceptional, (56)
"The property is amazing and the setting is idyllic. Loved every minute."
Elegant country retreat near Spring Green w expansive views of Driftless Region
Red Oak Lodge @ Spring Brook Resort
Exterior

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 AU$1,545
includes taxes & fees
28 Sept - 29 Sept
Red Oak Lodge @ Spring Brook Resort
Beach Lake Retreat with Private Lake and Hot Tub
Terrace/patio

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
Smart TV, fireplace, video games, DVD player

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
Indoor pool, a heated pool

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 AU$970
includes taxes & fees
29 Sept - 30 Sept
Dogwood Dream @ Spring Brook Resort
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

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
TV, fireplace, DVD player, table football

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
Exterior

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
Terrace/patio

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
Dining

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 AU$1,040
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
Fridge, microwave, oven, stovetop

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!
Smart TV, fireplace, books, stereo

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!
TV, fireplace

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
Fridge, microwave, oven, stovetop

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)
Terrace/patio

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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
719 Holiday Homes
Lowest Price
AU$771
Highest Price
AU$1,545

Explore a world of travel with Expedia

Explore a world of travel with Expedia