Holiday Homes in Southern Wisconsin

Start date: Check-in selected.
To Date
End date: Check-out
    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
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Featured Holiday Homes in Southern Wisconsin

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, (972)
"Great place to stay "
Tamarack Wisconsin Dells a Ramada by Wyndham
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Exterior

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (40)
"Gorgeous place!"
The price is NZ$413
includes taxes & fees
1 Oct - 2 Oct
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
Fridge, microwave, oven, stovetop

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

10.0 out of 10, Exceptional, (68)
"It is to nice that you get to stay in a house this nice- the lake is there and with that the sunset. It is well-stocked and very clean. It is a great place to stay"
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
Downtown 3BR Walkable Home Near UW, Stadium, Restaurants + Free Parking
Microwave, oven, stovetop, dishwasher

Downtown 3BR Walkable Home Near UW, Stadium, Restaurants + Free Parking

10.0 out of 10, Exceptional, (1)
"The home was in the perfect location, we loved being able to walk to eat! There’s a lot of cute coffee shops nearby too. The home itself was beautiful and I appreciate all the extra amenities like shampoo, body wash and extra towels and blankets! "
Downtown 3BR Walkable Home Near UW, Stadium, Restaurants + Free Parking
Private 2 BR Lower-Level Retreat Woods & Wildlife, within 10 min of Wis Dells
Fridge, microwave, oven, stovetop

Private 2 BR Lower-Level Retreat Woods & Wildlife, within 10 min of Wis Dells

10.0 out of 10, Exceptional, (2)
"Very nice place! "
Private 2 BR Lower-Level Retreat Woods & Wildlife, within 10 min of Wis Dells
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds

The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

10.0 out of 10, Exceptional, (246)
"Beautiful view, wonderful house. Great morings with coffee on balcony!!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Champagne Chalet @ Spring Brook Resort
Fridge, microwave, oven, stovetop

Champagne Chalet @ Spring Brook Resort

9.8 out of 10, Exceptional, (58)
"house was great, very spacious, good outdoor space, location was fantastic with short walk to clubhouse, clubhouse pool was great for kids, easy to get golf tee times. "
The price is NZ$1,785
includes taxes & fees
2 Oct - 3 Oct
Champagne Chalet @ Spring Brook Resort
Lakefront 2-bed house in Oshkosh with dock!
Terrace/patio

Lakefront 2-bed house in Oshkosh with dock!

10.0 out of 10, Exceptional, (33)
"This property is absolutely fantastic. Great location, comfortable bedding, and a gorgeous lake"
Lakefront 2-bed house in Oshkosh with dock!
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!
Fridge, microwave, oven, stovetop

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (44)
"Quiet and great location."
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!
A Pleasant Retreat- No Cleaning Fee & New Discounts
Property grounds

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (250)
"Wonderful place to stay. Very very clean and it met all our needs. Thank you! "
A Pleasant Retreat- No Cleaning Fee & New Discounts
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)
"Three generations staying at this beautiful home. Location quiet yet walkable to shopping. Close to water parks. The basketball court, stage and inside slide were a hit with the kids. Look forward to returning next year as we want to make this vacay an annual experience. "
The price is NZ$1,109
includes taxes & fees
1 Oct - 2 Oct
Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Fridge, microwave, oven, stovetop

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

9.8 out of 10, Exceptional, (106)
"Out bachelor party stay was fantastic, everything about the trip was a breeze! "
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
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, (19)
"The place was clean, and my family had a wonderful time during our stay."
The price is NZ$1,708
includes taxes & fees
1 Oct - 2 Oct
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
River Front Property
Smart TV, video games, books, stereo

River Front Property

10.0 out of 10, Exceptional, (100)
"Location was perfect! Patio was exceptional and had all the amenities we could ever need. Host had info for activities to do in the area. Location was close to the boat ramps. Would love to stay again! "
River Front Property
Log Cabin Lodge Devil's Lake State Park, Skiing, Cascade Mtn, Dells
Outdoor dining

Log Cabin Lodge Devil's Lake State Park, Skiing, Cascade Mtn, Dells

10.0 out of 10, Exceptional, (132)
"Lovely house "
Log Cabin Lodge Devil's Lake State Park, Skiing, Cascade Mtn, Dells
Large Lakefront Home on Lake Como - Private Pier!
Fridge, microwave, oven, stovetop

Large Lakefront Home on Lake Como - Private Pier!

9.8 out of 10, Exceptional, (24)
"We had a wonderful time, enjoying the amenities of the house and the surrounding area. I would 100% recommend it to family and friends."
Large Lakefront Home on Lake Como - Private Pier!
Canyon Cottage by Sundara & Wild Rock
Fridge, microwave, oven, stovetop

Canyon Cottage by Sundara & Wild Rock

9.2 out of 10, Wonderful, (5)
The price is NZ$615
includes taxes & fees
1 Oct - 2 Oct
Canyon Cottage by Sundara & Wild Rock
Cottage walking distance to Lake Geneva!
Property grounds

Cottage walking distance to Lake Geneva!

10.0 out of 10, Exceptional, (39)
"Comfortable cottage with great kitchen and 2 porches. We used it as a home base while visiting Lake Geneva, Elkhorn and Madison. I would definitely recommend it for anyone visiting Lake Geneva. "
Cottage walking distance to Lake Geneva!
Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine
Fridge, microwave, stovetop, dishwasher

Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine

10.0 out of 10, Exceptional, (14)
"Great neighborhood to stay. "
Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

10.0 out of 10, Exceptional, (13)
"Will come and stay again great host and home"
The price is NZ$552
includes taxes & fees
2 Oct - 3 Oct
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Wisconsin Hotel Reviews

DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

10/10 Excellent
"Clean room and newly decorated!!"
Adrian 1-night trip
Posted 2 days ago
DoubleTree by Hilton Madison East

Find out more about Southern Wisconsin

Find out more about Southern Wisconsin

Southern Wisconsin Holiday Homes information

Number of reviews
2,078
Accommodation
744 Holiday Homes
Lowest Price
NZ$413
Highest Price
NZ$1,785

Explore a world of travel with Expedia

Explore a world of travel with Expedia