Photo by Evae

Southern Wisconsin holiday rentals

We found 8,828 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Wisconsin

Showing deals for:8 Jan - 15 Jan

Private kitchen
Attic balcony
Exterior
Sitting area
Exceptional
(22 reviews)

Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

Delavan

8% off
AU$10,618
for 7 nights, 1 cottage
AU$1,517 per night
includes taxes & fees
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
Front room sitting area
Exterior
Kitchen and sitting area
Exterior
Exceptional
(43 reviews)

Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access

Delavan

8% off
AU$8,529
for 7 nights, 1 home
AU$1,218 per night
includes taxes & fees
Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access
Property grounds
Private kitchen
Full bed with Twin bunk beds
Main Kitchen
Exceptional
(45 reviews)

Cozy Cabin with a Hot Tub!

Wisconsin Dells

8% off
AU$5,169
for 7 nights, 1 cottage
AU$738 per night
includes taxes & fees
Cozy Cabin with a Hot Tub!
Living area
Terrace/patio
Exterior
Living area
Exceptional
(13 reviews)

Rifugio Graziella, King Bed, Hot Tub, Sauna, Soaking Tub, Fireplace, EV+, Luxury

Baraboo

13% off
AU$5,110
for 7 nights, 1 cabin
AU$730 per night
includes taxes & fees
Rifugio Graziella, King Bed, Hot Tub, Sauna, Soaking Tub, Fireplace, EV+, Luxury
Room
Terrace/patio
Living area
Exterior
Exceptional
(80 reviews)

Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!

Eastman

8% off
AU$1,309
for 7 nights, 1 room
AU$187 per night
includes taxes & fees
Hydro-Massage Tub! Wrangler Outlaw Suite! Horses!
Exterior
Private kitchen
Interior
Terrace/patio
Exceptional
(7 reviews)

Beautiful 4 bedroom home. Close to Downtown, Devil's Lake, and the Dells

Baraboo

7% off
AU$3,704
for 7 nights, 1 home
AU$529 per night
includes taxes & fees
Beautiful 4 bedroom home. Close to Downtown, Devil's Lake, and the Dells
Creative seating allows everyone to gather in the front porch
Chill on the front porch and set the night time vibes!
back porch mud room has access to the kitchen and back yard
Exterior lighting sets the mood for a magical evening
Exceptional
(27 reviews)

Fabulous! 5 BR/7 Bed: 15 min to the Dells, across from Lake Mason

Briggsville

8% off
AU$4,627
for 7 nights, 1 home
AU$661 per night
includes taxes & fees
Fabulous! 5 BR/7 Bed: 15 min to the Dells, across from Lake Mason
Living area
Exterior
Exterior
Private kitchen
Exceptional
(7 reviews)

Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access

Delavan

8% off
AU$10,568
for 7 nights, 1 home
AU$1,510 per night
includes taxes & fees
Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access
well built and only 15 years old
Property grounds
Interior
table for 10
Wonderful
(61 reviews)

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

Twin Lakes

8% off
AU$7,218
for 7 nights, 1 home
AU$1,031 per night
includes taxes & fees
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
View from the driveway.
Watch the sun come up with from this spacious patio.
Kitchen island into the dining area.
Interior
Exceptional
(92 reviews)

Beautiful Sunrises and Lakefront Views!

Fond du Lac

8% off
AU$3,428
for 7 nights, 1 home
AU$490 per night
includes taxes & fees
Beautiful Sunrises and Lakefront Views!
Exterior
Property grounds
Interior
Interior
Exceptional
(45 reviews)

Grand home with views of the Mississippi!

Trempealeau

8% off
AU$4,180
for 7 nights, 1 home
AU$597 per night
includes taxes & fees
Grand home with views of the Mississippi!
Living area
Great spot for your morning coffee
Exterior
16 feet of dining that can be expanded to add another 8 feet
Exceptional
(112 reviews)

Private Country House near Lake Geneva, Como and Williams Bay

Lake Geneva

8% off
AU$14,854
for 7 nights, 1 home
AU$2,122 per night
includes taxes & fees
Private Country House near Lake Geneva, Como and Williams Bay
Private kitchen
Exterior
Outdoor dining
Room
Exceptional
(148 reviews)

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

Baraboo

8% off
AU$5,460
for 7 nights, 1 home
AU$780 per night
includes taxes & fees
Log Cabin Lodge Devil's Lake State Park, Skiing, Cascade Mtn, Dells
Exterior
Your new favorite indoor coffee spot.
Serveware for 10.
Breakfast bar with room for four.
Exceptional
(13 reviews)

Modern | Beachfront | Sleeps 10

Oostburg

12% off
AU$8,663
for 7 nights, 1 home
AU$1,238 per night
includes taxes & fees
Modern | Beachfront | Sleeps 10
Queen Room
Autumn view
Relaxing Living Room
Well appointed Kitchen
Exceptional
(59 reviews)

Adorable Updated Cozy Cottage set on Lake Wisconsin's Sunset Bay

Lodi

9% off
AU$3,216
for 7 nights, 1 cottage
AU$459 per night
includes taxes & fees
Adorable Updated Cozy Cottage set on Lake Wisconsin's Sunset Bay
Kohler/Andrae a short drive away featuring wildlife, nature, and beach.
Fully stocked and appointed kitchen for hosting groups.
Sheboygan Shores mud room.
Large sandy beach located 0.2 miles from Sheboygan Shores!
Exceptional
(13 reviews)

Sheboygan Shores

Sheboygan

7% off
AU$4,024
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Sheboygan Shores
Entryway
Fire pit in backyard
Family room on lower level
Primary bedroom with king bed and en suite bathroom- on main level
Exceptional
(211 reviews)

Beautiful Lake Delavan/Lake Geneva Vacation Home

Delavan

8% off
AU$2,831
for 7 nights, 1 home
AU$404 per night
includes taxes & fees
Beautiful Lake Delavan/Lake Geneva Vacation Home
Interior
Exterior
Marina
Living area
Exceptional
(20 reviews)

Firefly Cottage! Book your Fall trip today before the calendar fills up!

Bagley

8% off
AU$1,551
for 7 nights, 1 cottage
AU$222 per night
includes taxes & fees
Firefly Cottage! Book your Fall trip today before the calendar fills up!
Room
Interior
Exterior
Living area
Exceptional
(34 reviews)

Beautifully remodeled 2 bed 104 Berkley Verona #6

Verona

16% off
AU$1,730
for 7 nights, 1 home
AU$247 per night
includes taxes & fees
Beautifully remodeled 2 bed 104 Berkley Verona #6
Interior
Private kitchen
Living area
Outdoor dining
Exceptional
(88 reviews)

Cozy & Spacious Home Near Downtown Viroqua - 4BR + Bonus Basement Sleeping

Viroqua

8% off
AU$2,373
for 7 nights, 1 home
AU$339 per night
includes taxes & fees
Cozy & Spacious Home Near Downtown Viroqua - 4BR + Bonus Basement Sleeping
Exterior
Exterior
Interior
Front door entry into living room with lake view and fireplace
Exceptional
(27 reviews)

Waterfront Lake Koshkonong Retreat - 5BR with Fire Pit, Pier & Social Garage

Edgerton

8% off
AU$4,628
for 7 nights, 1 home
AU$661 per night
includes taxes & fees
Waterfront Lake Koshkonong Retreat - 5BR with Fire Pit, Pier & Social Garage
Entrance
Second firepit hidden in the forest
Dining area
Patio
Exceptional
(91 reviews)

Wisconsin Dells Cabin in the Woods

Wisconsin Dells

8% off
AU$2,647
for 7 nights, 1 cabin
AU$378 per night
includes taxes & fees
Wisconsin Dells Cabin in the Woods
Rome Town Center has plenty to offer for the family.
Sand Valley - Standing at Craig's Porch, the Clubhouse is off in the distance
Living Room with Gas Fireplace
You can't beat the beautiful view of the Pines Course at Lake Arrowhead.
Exceptional
(35 reviews)

Be Blessed at Kinship Casa in Rome, WI

Nekoosa

7% off
AU$2,473
for 7 nights, 1 home
AU$353 per night
includes taxes & fees
Be Blessed at Kinship Casa in Rome, WI
Room
Outdoor spa tub
Private kitchen
Living area
Exceptional
(556 reviews)

Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

Ferryville

13% off
AU$2,016
for 7 nights, 1 home
AU$288 per night
includes taxes & fees
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Southern Wisconsin getaway

Learn about the unique charm of Southern Wisconsin with a stay in a holiday home rental. This city has something for everyone. Kalahari Indoor Waterpark and Lake Michigan are just a couple of the must-see attractions. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Southern Wisconsin

Are you hoping to find attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Southern Wisconsin a fun spot to go on holiday. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Kalahari Indoor Waterpark (16 mi / 25.8 km)
  • Cascade Mountain Ski Area (4.6 mi / 7.4 km)
  • Devil's Head Ski Resort (5.8 mi / 9.4 km)
  • Wollersheim Winery (14 mi / 22.5 km)
  • Great Wolf Lodge Water Park (16.6 mi / 26.7 km)
  • Wild West Waterpark (17.3 mi / 27.9 km)

Exploring the natural features in Southern Wisconsin

Whether you're looking for adventure or just want to take in the scenery, Southern Wisconsin is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Wisconsin (5.6 mi / 9.1 km)
  • Parfrey's Glen State Natural Area (6.5 mi / 10.4 km)
  • Ice Age Trail Trailhead (7.3 mi / 11.8 km)
  • Gibraltar Rock State Natural Area (7.5 mi / 12.1 km)
  • Glacial Lake Wisconsin (9.9 mi / 15.9 km)
  • South Shore Beach (10.9 mi / 17.5 km)

Transport options to and around Southern Wisconsin

Fly into Dane County Regional Airport (MSN), the closest airport, located 22.1 mi (35.5 km) from the city centre.

If you're travelling by train, Portage Station, Wisconsin Dells Station and Madison Station are the main stations in the area. Utilise the area's public transport and catch a ride on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop if you're interested in seeing more of the city.

Frequently asked questions

What is the best area to stay in Southern Wisconsin when booking a holiday home?
One of the more sought-after areas to choose a holiday home in Southern Wisconsin is Lake Delton. Stay here and discover some top attractions, like Kalahari Indoor Waterpark and Noahs Ark Waterpark.
What is the most popular type of holiday home accommodation in Southern Wisconsin?
According to our data, houses are the most in-demand type of holiday home in Southern Wisconsin. But as you might expect, everyone's idea of the perfect trip can differ. Stayz has holiday homes of all shapes and sizes, so you're bound to find the perfect fit for you.
How much does it cost to rent a holiday home in Southern Wisconsin?
Several things can affect what you'll pay for a holiday home in Southern Wisconsin, like the time of year, length of stay and property type. Still, all our holiday homes have something in common — exceptional value. Simply enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Southern Wisconsin?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Enter your Southern Wisconsin travel dates to view your available options on Stayz. Can't live without a private pool? Use our filters to pick the features and amenities you need.
What are popular home amenities in Southern Wisconsin?
When it comes to home amenities that people are on the lookout for in Southern Wisconsin, a stovetop, a microwave oven and a fridge are the most popular. With Stayz holiday homes, you'll have options to suit your taste and style, whether you're on a trip with friends, relatives or even pets.
Are there large group holiday homes in Southern Wisconsin?
With 916 properties that can host 10 or more people in Southern Wisconsin, there's no need to keep anyone off the invite list. From family get-togethers to events like Christmas and birthday parties, Stayz will help you find a large group home to match the occasion.
What are the top attractions for families in Southern Wisconsin?
Keep the kids busy at these fabulous family-friendly attractions in Southern Wisconsin:
  • Kalahari Indoor Waterpark
  • Noahs Ark Waterpark
  • American Family Field
Can I find two-bedroom holiday homes in Southern Wisconsin?
You can pick from 1 ,422 two-bedroom holiday homes in Southern Wisconsin. Settle the kids into the second room or maybe fill it with a couple of your besties. There's ample space for whoever's lucky enough to be joining in on the fun.
Are there holiday homes with WiFi in Southern Wisconsin?
Southern Wisconsin has 1 ,595 holiday homes with WiFi, so you can stay connected while on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to scrolling social media, these Stayz homes will keep you online.
How old do you have to be to rent a holiday home in Southern Wisconsin?
The minimum age requirements can vary across properties on Stayz, so look at the rules of the holiday home in Southern Wisconsin you want to book. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Southern Wisconsin for?
How long you can book a holiday home in Southern Wisconsin varies according to the property. Simply enter your preferred travel dates to see a list of options offering extended stays. With many features like kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover someplace just right to call your home away from home in Southern Wisconsin.

More holiday ideas