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Southern Wisconsin holiday rentals

We found 8,924 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southern Wisconsin

Showing deals for:27 Nov - 4 Dec

Golf
Interior
master bedroom with master bath.
Living room
Wonderful
(59 reviews)

78 Acres, On the Prairie, with a Small Trout Stream in the Driftless.

Blanchardville

21% off
AU$1,262
for 7 nights, 1 room
AU$180 per night
includes taxes & fees
78 Acres, On the Prairie, with a Small Trout Stream in the Driftless.
Private kitchen
Attic balcony
Sitting area
Dining area
Exceptional
(20 reviews)

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

Delavan

8% off
AU$13,780
for 7 nights, 1 cottage
AU$1,969 per night
includes taxes & fees
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
Living area
Exterior
Dining
Outdoor spa tub
Exceptional
(47 reviews)

Cozy Secluded Cabin w/ Hot Tub, Relax, Unwind & Stargaze

Ferryville

8% off
AU$2,834
for 7 nights, 1 cabin
AU$405 per night
includes taxes & fees
Cozy Secluded Cabin w/ Hot Tub, Relax, Unwind & Stargaze
Front Entrance-thanks to my past guests who helped me keep my flowers beautiful!
Interior
Private kitchen
Exterior
Exceptional
(103 reviews)

Executive Lakefront Home 30 Minutes From Madison!

Fort Atkinson

9% off
AU$8,052
for 7 nights, 1 home
AU$1,150 per night
includes taxes & fees
Executive Lakefront Home 30 Minutes From Madison!
Main channel sunset
Living room looking down from loft
Welcome to Rustic Ridge Chalet
The cabin overlooks the Mississippi River sunsets
Exceptional
(31 reviews)

NEW!!! GRAND VIEW -- Rustic Ridge Chalet, hot tub, river view, privacy

De Soto

12% off
AU$2,757
for 7 nights, 1 cabin
AU$394 per night
includes taxes & fees
NEW!!! GRAND VIEW -- Rustic Ridge Chalet, hot tub, river view, privacy
Blackwolf Run Golf Course. https://www.destinationkohler.com/golf/blackwolf-run
Blue Harbor Resort. https://www.blueharborresort.com/
Kohler Waters Spa https://www.americanclubresort.com/spa/kohler-waters-spa
The Bull at Pinehurst Farms. https://golfthebull.com/
Exceptional
(140 reviews)

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Oostburg

9% off
AU$1,553
for 7 nights, 1 home
AU$222 per night
includes taxes & fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Loft area overlooking great room
Great room viewed from the loft
Main level bedroom with king size bed, glider, and walk-in closet
Main level great room
Exceptional
(62 reviews)

Cozy Cabin in the Woods with fishing and golf nearby

Valders

25% off
AU$3,260
for 7 nights, 1 home
AU$466 per night
includes taxes & fees
Cozy Cabin in the Woods with fishing and golf nearby
Private kitchen
Interior
Living area
Living area
Exceptional
(147 reviews)

Secluded Rustic-Modern Log Cabin w/ Hot Tub, Private Creekside Escape

Ferryville

8% off
AU$2,834
for 7 nights, 1 cabin
AU$405 per night
includes taxes & fees
Secluded Rustic-Modern Log Cabin w/ Hot Tub, Private Creekside Escape
Living area
Exterior
Interior
Marina
Exceptional
(16 reviews)

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

Bagley

8% off
AU$1,402
for 7 nights, 1 cottage
AU$200 per night
includes taxes & fees
Firefly Cottage! Book your Summer trip today before the calendar fills up!
Deck
Open concept living and dining room
Bright kitchen with brand new stainless steel appliances
Exterior
Exceptional
(15 reviews)

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth

6% off
AU$3,744
for 7 nights, 1 home
AU$535 per night
includes taxes & fees
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Dining
Living area
Living area
Private kitchen
Exceptional
(10 reviews)

Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle

Oconomowoc

9% off
AU$34,265
for 7 nights, 1 home
AU$4,895 per night
includes taxes & fees
Kohl Manor Luxury Lake 8br year round retreat Pool, Cinema, Arcade on LacLaBelle
upper level sitting area
Back view of lodge
Deer Haven's Relaxing Private Hot Tub
Lodge Kitchen area
Wonderful
(99 reviews)

Luxurious & Spacious! A Great Place For Family, Friends, Reunions & Corporate!

Adams

8% off
AU$14,925
for 7 nights, 1 room
AU$2,132 per night
includes taxes & fees
Luxurious & Spacious! A Great Place For Family, Friends, Reunions & Corporate!
Living area
Private kitchen
Living area
Room
Exceptional
(43 reviews)

Cozy Cabin Retreat located just minutes to Galena, IL & DBQ, IA

Hazel Green

8% off
AU$2,111
for 7 nights, 1 cabin
AU$302 per night
includes taxes & fees
Cozy Cabin Retreat located just minutes to Galena, IL & DBQ, IA
Kitchen and sitting area
Exterior
Exterior
Private kitchen
Exceptional
(42 reviews)

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

Delavan

8% off
AU$10,707
for 7 nights, 1 home
AU$1,530 per night
includes taxes & fees
Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access
Fire pit
Front view
View from loft
View from the deck
Exceptional
(229 reviews)

Hana Log Cabin near Devil's Lake

Baraboo

7% off
AU$4,990
for 7 nights, 1 cabin
AU$713 per night
includes taxes & fees
Hana Log Cabin near Devil's Lake
Living area
Dining
Living area
Interior
Exceptional
(63 reviews)

Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.

Cochrane

9% off
AU$2,020
for 7 nights, 1 room
AU$289 per night
includes taxes & fees
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Family Room looking out to lake.
House from lake
Second Floor Primary Bedroom
Dining area
Exceptional
(183 reviews)

Grande Vista Manor-Beautiful Lakefront Home Minutes From Lake Geneva

Genoa City

5% off
AU$7,461
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
Grande Vista Manor-Beautiful Lakefront Home Minutes From Lake Geneva
Interior
Terrace/patio
Dining
Soaking Tub (Jetted tub) accessed from outside tucked under deck
Exceptional
(124 reviews)

SereniTree Cabin - Modern Rustic Getaway tucked in the trees

Eastman

12% off
AU$2,192
for 7 nights, 1 cabin
AU$313 per night
includes taxes & fees
SereniTree Cabin - Modern Rustic Getaway tucked in the trees
View of farmhouse from lighthouse
Terrace/patio
Basement area
Room
Exceptional
(40 reviews)

Cozy Farmhouse Retreat, Climb lighthouse, Acres to explore, Dogs ok, Amenities!

Cuba City

8% off
AU$2,642
for 7 nights, 1 home
AU$377 per night
includes taxes & fees
Cozy Farmhouse Retreat, Climb lighthouse, Acres to explore, Dogs ok, Amenities!
Interior
Terrace/patio
Room
Private kitchen
Wonderful
(17 reviews)

Beautiful, cozy 3 bedroom cabin with additional loft space near water park!

Warrens

8% off
AU$2,250
for 7 nights, 1 cabin
AU$321 per night
includes taxes & fees
Beautiful, cozy 3 bedroom cabin with additional loft space near water park!
Living Room
Street view with Front porch and Garage
Dining Room, Breakfast Bar and Kitchen
Master Bedroom with balcony and Lake Michigan view!
Exceptional
(264 reviews)

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan

7% off
AU$1,894
for 7 nights, 1 home
AU$271 per night
includes taxes & fees
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Interior
Exterior
Living area
Front door entry into living room with lake view and fireplace
Exceptional
(23 reviews)

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

Edgerton

8% off
AU$5,518
for 7 nights, 1 home
AU$788 per night
includes taxes & fees
Waterfront Lake Koshkonong Retreat - 5BR with Fire Pit, Pier & Social Garage
Room
Terrace/patio
Living area
Exterior
Exceptional
(5 reviews)

Soaker Tub & Sunset Wanlass Retreat

Mindoro

17% off
AU$1,821
for 7 nights, 1 home
AU$260 per night
includes taxes & fees
Soaker Tub & Sunset Wanlass Retreat
Living area
Living area
Room
Private kitchen
Exceptional
(57 reviews)

Charming cottage on Lake Winnebago

Neenah

8% off
AU$3,468
for 7 nights, 1 cottage
AU$495 per night
includes taxes & fees
Charming cottage on Lake Winnebago

  • 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 Noah's Ark Waterpark 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)
  • Noah's Ark Waterpark (18.2 mi / 29.2 km)
  • Mt. Olympus Water and Theme Park (18.8 mi / 30.3 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)

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)
  • Glacial Lake Wisconsin (9.9 mi / 15.9 km)
  • Devil's Lake (11 mi / 17.8 km)
  • Wisconsin River (15.4 mi / 24.7 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.

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