Photo by Inbal Arieh

Southwest Wisconsin holiday homes

We found 4,177 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Wisconsin

Showing deals for:27 Nov - 4 Dec

Living area
Dining
Private kitchen
Room
Exceptional
(212 reviews)

Madison & ~UW~-Madison Area Lakefront Home

McFarland

8% off
NZ$6,347
for 7 nights, 1 cottage
NZ$907 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.
Fully equipped kitchen.
Large kitchen walks out onto 1st floor deck.
Exceptional
(55 reviews)

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

Cambridge

8% off
NZ$5,650
for 7 nights, 1 home
NZ$807 per night
includes taxes & fees
Waterfront Lake Ripley getaway. Kayak, paddleboard and fish from private pier!
Bathroom
Interior
master bedroom with master bath.
Living room
Wonderful
(60 reviews)

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

Blanchardville

21% off
NZ$1,535
for 7 nights, 1 room
NZ$219 per night
includes taxes & fees
78 Acres, On the Prairie, with a Small Trout Stream in the Driftless.
Interior
Interior
Interior
Dining
Exceptional
(40 reviews)

5 bedroom - Parsonage of Glen Haven

Glen Haven

8% off
NZ$2,049
for 7 nights, 1 home
NZ$293 per night
includes taxes & fees
5 bedroom - Parsonage of Glen Haven
Living area
Exterior
Outdoor spa tub
Dining
Exceptional
(47 reviews)

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

Ferryville

8% off
NZ$3,446
for 7 nights, 1 cabin
NZ$492 per night
includes taxes & fees
Cozy Secluded Cabin w/ Hot Tub, Relax, Unwind & Stargaze
Exterior
Attic balcony
Dining area
Sitting area
Exceptional
(20 reviews)

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

Delavan

8% off
NZ$16,648
for 7 nights, 1 cottage
NZ$2,378 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
Exterior
Front Entrance-thanks to my past guests who helped me keep my flowers beautiful!
Exceptional
(103 reviews)

Executive Lakefront Home 30 Minutes From Madison!

Fort Atkinson

9% off
NZ$9,913
for 7 nights, 1 home
NZ$1,416 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
NZ$3,323
for 7 nights, 1 cabin
NZ$475 per night
includes taxes & fees
NEW!!! GRAND VIEW -- Rustic Ridge Chalet, hot tub, river view, privacy
Newly stained exterior with updated landscaping and wrap around deck.
Every room is designed to enjoy the beauty and nature that surrounds you.
Beautifully landscaped yard.
Split Foyer with original Birch Mural is a favorite feature.
Exceptional
(133 reviews)

Luxury Bluff Retreat • 10 Minutes to Downtown

La Crosse

8% off
NZ$6,920
for 7 nights, 1 home
NZ$989 per night
includes taxes & fees
Luxury Bluff Retreat • 10 Minutes to Downtown
Terrace/patio
Interior
Living area
Private kitchen
Exceptional
(147 reviews)

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

Ferryville

8% off
NZ$3,446
for 7 nights, 1 cabin
NZ$492 per night
includes taxes & fees
Secluded Rustic-Modern Log Cabin w/ Hot Tub, Private Creekside Escape
Living area
Private kitchen
Interior
Interior
Exceptional
(87 reviews)

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

Viroqua

8% off
NZ$2,737
for 7 nights, 1 home
NZ$391 per night
includes taxes & fees
Cozy & Spacious Home Near Downtown Viroqua - 4BR + Bonus Basement Sleeping
Property grounds
Patio over water
Dining Room overlooking yard and river
Full Kitchen with island
Exceptional
(5 reviews)

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

Janesville

12% off
NZ$8,812
for 7 nights, 1 home
NZ$1,259 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
NZ$1,704
for 7 nights, 1 cottage
NZ$243 per night
includes taxes & fees
Firefly Cottage! Book your Summer trip today before the calendar fills up!
The living area with comfy sofa and chair and fire
Spend nights curled up by the fire in the cosy living area. Suitable for all seasons
Sit and relax on the porch and take in the views!
Cozy Living & Dining Areas: Lounge by the fireplace, enjoy TV, or stream via Wi-Fi
Exceptional
(16 reviews)

Crooked Creek - Serenity Cabin

Boscobel

8% off
NZ$1,455
for 7 nights, 1 cabin
NZ$208 per night
includes taxes & fees
Crooked Creek - Serenity Cabin
Upper level living/tv area
Exterior
Upper level table/bar
Bedroom 3 upper level
Exceptional
(62 reviews)

Rustic Lake home Retreat

Edgerton

7% off
NZ$2,983
for 7 nights, 1 home
NZ$426 per night
includes taxes & fees
Rustic Lake home Retreat
Deer Haven's Relaxing Private Hot Tub
Back view of lodge
upper level sitting area
Lodge Kitchen area
Wonderful
(99 reviews)

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

Adams

8% off
NZ$18,065
for 7 nights, 1 room
NZ$2,581 per night
includes taxes & fees
Luxurious & Spacious! A Great Place For Family, Friends, Reunions & Corporate!
Private kitchen
Exterior
Living area
Exterior
Exceptional
(5 reviews)

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

Delavan

8% off
NZ$13,257
for 7 nights, 1 home
NZ$1,894 per night
includes taxes & fees
Brand New Lakeview Retreat: Beautiful Delavan Lake Views & Private Lake Access
Exterior
Exterior
Private kitchen
Front room sitting area
Exceptional
(42 reviews)

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

Delavan

7% off
NZ$13,528
for 7 nights, 1 home
NZ$1,933 per night
includes taxes & fees
Stunning Lakeside Retreat: Delavan Lake Home with Lake Views & Lake Access
Living area
Private kitchen
Living area
Room
Exceptional
(43 reviews)

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

Hazel Green

9% off
NZ$2,508
for 7 nights, 1 cabin
NZ$358 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
NZ$6,642
for 7 nights, 1 cabin
NZ$949 per night
includes taxes & fees
Rifugio Graziella, King Bed, Hot Tub, Sauna, Soaking Tub, Fireplace, EV+, Luxury
Stairs to the loft area
Front view
View from loft
View from the deck
Exceptional
(229 reviews)

Hana Log Cabin near Devil's Lake

Baraboo

6% off
NZ$6,069
for 7 nights, 1 cabin
NZ$867 per night
includes taxes & fees
Hana Log Cabin near Devil's Lake
Exterior
Terrace/patio
Dining
Soaking Tub (Jetted tub) accessed from outside tucked under deck
Exceptional
(125 reviews)

SereniTree Cabin - Modern Rustic Getaway tucked in the trees

Eastman

12% off
NZ$2,606
for 7 nights, 1 cabin
NZ$372 per night
includes taxes & fees
SereniTree Cabin - Modern Rustic Getaway tucked in the trees
Property grounds
Terrace/patio
View of farmhouse from lighthouse
Basement area
Exceptional
(40 reviews)

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

Cuba City

8% off
NZ$3,186
for 7 nights, 1 home
NZ$455 per night
includes taxes & fees
Cozy Farmhouse Retreat, Climb lighthouse, Acres to explore, Dogs ok, Amenities!
Exterior
Exterior
Interior
Living area
Exceptional
(23 reviews)

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

Edgerton

8% off
NZ$6,775
for 7 nights, 1 home
NZ$968 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. Bookabach 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 Bookabach 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 Bookabach 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 Bookabach 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 Bookabach 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 Bookabach, 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.

More holiday ideas