Photo by Inbal Arieh

Southwest Wisconsin holiday rentals

We found 4,178 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Wisconsin

Showing deals for:27 Nov - 4 Dec

Private kitchen
Dining
Dining room and kitchen
Room
Exceptional
(212 reviews)

Madison & ~UW~-Madison Area Lakefront Home

McFarland

8% off
AU$5,157
for 7 nights, 1 cottage
AU$737 per night
includes taxes & fees
Madison & ~UW~-Madison Area Lakefront Home
Lake side of home. Relax and enjoy views of the lake from upper and lower decks.
View of the lake from the upper level master bedroom.
Large kitchen walks out onto 1st floor deck.
Fully equipped kitchen.
Exceptional
(55 reviews)

Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!

Cambridge

8% off
AU$4,588
for 7 nights, 1 home
AU$655 per night
includes taxes & fees
Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!
master bedroom with master bath.
Interior
Golf
Bathroom
Wonderful
(60 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.
Dining
Interior
Interior
Interior
Exceptional
(40 reviews)

5 bedroom - Parsonage of Glen Haven

Glen Haven

8% off
AU$1,684
for 7 nights, 1 home
AU$241 per night
includes taxes & fees
5 bedroom - Parsonage of Glen Haven
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
Exterior
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$13,781
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
Huge Dining Room Table....can be extended to sit 16 people
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
Split Foyer with original Birch Mural is a favorite feature.
Every room is designed to enjoy the beauty and nature that surrounds you.
Beautifully landscaped yard.
The open layout makes it easy to share quality time.
Exceptional
(133 reviews)

Luxury Bluff Retreat • 10 Minutes to Downtown

La Crosse

8% off
AU$5,642
for 7 nights, 1 home
AU$806 per night
includes taxes & fees
Luxury Bluff Retreat • 10 Minutes to Downtown
Living area
Interior
Living area
Terrace/patio
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
Interior
Private kitchen
Interior
Living area
Exceptional
(87 reviews)

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

Viroqua

8% off
AU$2,303
for 7 nights, 1 home
AU$329 per night
includes taxes & fees
Cozy & Spacious Home Near Downtown Viroqua - 4BR + Bonus Basement Sleeping
Property grounds
Patio over water
Living area
Full Kitchen with island
Exceptional
(5 reviews)

Waterfront retreat with pier near Woodman's convention ctr & downtown Janesville

Janesville

12% off
AU$7,210
for 7 nights, 1 home
AU$1,030 per night
includes taxes & fees
Waterfront retreat with pier near Woodman's convention ctr & downtown Janesville
Exterior detail
Exterior
Interior
Living area
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!
Sit and relax on the porch and take in the views!
Spend nights curled up by the fire in the cosy living area. Suitable for all seasons
The living area with comfy sofa and chair and fire
Comfortable All-Season Cabin: Heating and air conditioning keep you cozy year-round
Exceptional
(16 reviews)

Crooked Creek - Serenity Cabin

Boscobel

8% off
AU$1,197
for 7 nights, 1 cabin
AU$171 per night
includes taxes & fees
Crooked Creek - Serenity Cabin
Private kitchen
Exterior
Upper level table/bar
Bedroom 3 upper level
Exceptional
(62 reviews)

Rustic Lake home Retreat

Edgerton

7% off
AU$2,475
for 7 nights, 1 home
AU$354 per night
includes taxes & fees
Rustic Lake home Retreat
Lodge Kitchen area
Back view of lodge
Deer Haven Great Room With Big Screen Tv
upper level sitting area
Wonderful
(99 reviews)

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

Adams

8% off
AU$14,926
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
Exterior
Exterior
Private kitchen
Exceptional
(5 reviews)

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

Delavan

8% off
AU$10,488
for 7 nights, 1 home
AU$1,498 per night
includes taxes & fees
Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access
Private kitchen
Exterior
Front room sitting area
Kitchen and sitting area
Exceptional
(42 reviews)

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

Delavan

8% off
AU$10,708
for 7 nights, 1 home
AU$1,530 per night
includes taxes & fees
Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access
Living area
Private kitchen
Living area
Exterior
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
Living area
Terrace/patio
Interior
Living area
Exceptional
(10 reviews)

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

Baraboo

13% off
AU$5,408
for 7 nights, 1 cabin
AU$773 per night
includes taxes & fees
Rifugio Graziella, King Bed, Hot Tub, Sauna, Soaking Tub, Fireplace, EV+, Luxury
View from the deck
Front view
View from loft
Fire pit
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
Exterior
Terrace/patio
Interior
Dining
Exceptional
(125 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
Room
Property grounds
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!
Front door entry into living room with lake view and fireplace
Exterior
Exterior
Living area
Exceptional
(23 reviews)

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

Edgerton

8% off
AU$5,519
for 7 nights, 1 home
AU$788 per night
includes taxes & fees
Waterfront Lake Koshkonong Retreat - 5BR with Fire Pit, Pier & Social Garage

  • 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

The riverfront setting of Southwest Wisconsin is ready to explore

The area's entertainment and festivals are just some of the reasons to come on holiday to Southwest Wisconsin. This city's water park, riverfront and shopping draw many visitors. Kalahari Indoor Waterpark and Noah's Ark Waterpark are just a couple of the must-see attractions. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Southwest Wisconsin

Are you searching for attractions to visit while you're in the area? Venture out of your holiday home and check out everything that Southwest Wisconsin has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Kalahari Indoor Waterpark (15.7 mi / 25.3 km)
  • Noah's Ark Waterpark (16.3 mi / 26.3 km)
  • Christmas Mountain (13.8 mi / 22.3 km)
  • Great Wolf Lodge Water Park (15.3 mi / 24.6 km)
  • Spring Brook Golf Course (15.4 mi / 24.7 km)
  • Wild West Waterpark (15.8 mi / 25.4 km)

Exploring the natural features in Southwest Wisconsin

Travellers enjoy Southwest Wisconsin for its riverfront and lakeside setting. Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Southwest Wisconsin is a great place to spend some time outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Redstone (11 mi / 17.6 km)
  • Mirror Lake State Park (13.8 mi / 22.1 km)
  • Devil's Lake (15.7 mi / 25.2 km)
  • Lake Delton (16.5 mi / 26.5 km)
  • Glacial Lake Wisconsin (16.9 mi / 27.1 km)
  • Woodside Sports Complex (19.1 mi / 30.8 km)

How to get to and around Southwest Wisconsin

The nearest airport is in Dane County Regional Airport (MSN), located 41.2 mi (66.2 km) from the city centre.

If you prefer to travel by train, Wisconsin Dells Station, Portage Station and Madison Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Southwest Wisconsin when booking a holiday home?
Lake Delton is one of the most well-liked areas to select a holiday home in Southwest Wisconsin. Looking for some top things to do here? Be sure to check out Kalahari Indoor Waterpark and Noahs Ark Waterpark.
What is the most popular type of holiday home accommodation in Southwest Wisconsin?
Based on our data, condos are the most sought-after holiday property type in Southwest Wisconsin. But as you know, everyone's idea of the perfect trip isn't the same. Stayz has holiday homes with every shape, size and budget in mind, and we'll help you to find your ideal match.
How much does it cost to rent a holiday home in Southwest Wisconsin?
Season, length of stay and property type are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your ideal escape. From cosy country cottages to sprawling villas, all Stayz holiday homes offer terrific value.
How much does it cost to rent a beach house in Southwest Wisconsin?
Prices for beach houses in Southwest Wisconsin can differ depending on the type and size of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and the number of guests to view holiday home options and prices. From there you can use the filters to refine your search by amenities, nearby activities, ratings and more.
What are popular home amenities in Southwest Wisconsin?
When it comes to home amenities that guests are searching for in Southwest Wisconsin, a fridge, a microwave oven and off-street parking options are at the top of the list. With Stayz holiday homes, there are choices to fit your taste and style, whether you're on a trip with your partner, your family or even pets.
Are there large group holiday homes in Southwest Wisconsin?
Southwest Wisconsin has 431 holiday homes that can accommodate 10 or more people. These properties come with the space you need to share good times with friends and family.
What are the top attractions for families in Southwest Wisconsin?
Keeping the kiddos entertained during your holiday in Southwest Wisconsin is child's play with these top family-friendly attractions:
  • Kalahari Indoor Waterpark
  • Noahs Ark Waterpark
  • Mt. Olympus Water and Theme Park
Can I find two-bedroom holiday homes in Southwest Wisconsin?
Gather your besties and enjoy total privacy and comfort in one of the 914 two-bedroom holiday homes Southwest Wisconsin has to offer.
Are there holiday homes with WiFi in Southwest Wisconsin?
Southwest Wisconsin has 681 holiday homes with WiFi, so you'll be able to stay connected during your trip. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming TV shows with the family to posting pics on social media, these Stayz homes make it a cinch to get online.
How old do you have to be to rent a holiday home in Southwest Wisconsin?
Age restrictions can differ between properties on Stayz, so double-check the rules of the holiday home in Southwest Wisconsin you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Southwest Wisconsin for?
The length of time you can book a holiday home in Southwest Wisconsin differs according to the property. Just enter your chosen dates to display a list of options offering extended stays. With loads of amenities such as kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere perfect to call your home away from home in Southwest Wisconsin.

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