A lighthouse and a house with a red roof.

Southern Wisconsin Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southern Wisconsin vacation rentals

A spacious living area with a fireplace, a sofa, and a dining area in the background.

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,095 reviews)
"Nice place and good breakfast"
United States
Kristin
$138 nightly
The price is $157
Oct 18 - Oct 19
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

2. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,461 reviews)
"I love this place"
United States
Edgar
$161 nightly
The price is $180
Oct 20 - Oct 21
Total with taxes and fees
Timber Ridge Lodge and Waterpark
A cabin with a dining area, a bicycle, and a sign reading "Vangelis".

3. Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
2.0 star property
Wild Rose
9.8 out of 10, Exceptional, (144 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
$150 nightly
The price is $158
Oct 29 - Oct 30
Total with taxes and fees
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

4. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,264 reviews)
"Super friendly staff, perfect hotel for romantic gateway."
United States
Daniel
$217 nightly
The price is $246
Oct 1 - Oct 2
Total with taxes and fees
Mill Creek Hotel
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

5. Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (50 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
$182 nightly
The price is $192
Oct 4 - Oct 5
Total with taxes and fees
Gleason's Chouse
A serene park with a pond, lush green grass, and a house in the background.

6. Country home with flowing river

Country home with flowing river
Pardeeville
9.0 out of 10, Wonderful, (177 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
$159 nightly
The price is $168
Oct 1 - Oct 2
Total with taxes and fees
Country home with flowing river
A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

7. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,252 reviews)
"Parking was reasonable and close by"
United States
Danita
$178 nightly
The price is $210
Oct 13 - Oct 14
Total with taxes and fees
The Plaza Hotel
A rural landscape with a wooden fence, a field of crops, and distant buildings including a silo and a house.

8. Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Peaceful Country Comfort W Panoramic Views of Big Creek Valley
Sparta
10.0 out of 10, Exceptional, (159 reviews)
"Loved the view and the peaceful setting! Very comfortable apartment, everything we needed and more. Perfect stay!"
United States
Nancy
$174 nightly
The price is $184
Oct 1 - Oct 2
Total with taxes and fees
Peaceful Country Comfort W Panoramic Views of Big Creek Valley
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

9. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
$137 nightly
The price is $158
Oct 25 - Oct 26
Total with taxes and fees
The Dylin
A wooden cabin with a porch, a picnic table, and a mailbox.

10. Quiet And Beautiful!!

Quiet And Beautiful!!
Warrens
9.2 out of 10, Wonderful, (204 reviews)
"Great place to stay comfortable and easy to access"
United States
Matthew
$314 nightly
The price is $331
Oct 1 - Oct 2
Total with taxes and fees
Quiet And Beautiful!!
A wooden cabin with a porch, two windows, and a star decoration on the wall.

11. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
$206 nightly
The price is $217
Oct 1 - Oct 2
Total with taxes and fees
River Road Retreat
A beachside area with a sandy shore, a small dock, and several beach huts.

12. Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
8.0 out of 10, Very good, (7 reviews)
"Me and my brother had an incredible time here. It was exactly what we were looking for. From the staff, to the property and the room itself. The natures walls close by. It was great and will be returning with more of the family again."
United States
Jessica
$190 nightly
The price is $200
Oct 1 - Oct 2
Total with taxes and fees
Tiki Beach Campground
A log cabin with a large porch, multiple windows, and a stone pathway leading to the entrance.

13. Rustic Hideaway Sleeps 4 HOT TUB

Rustic Hideaway Sleeps 4 HOT TUB
De Soto
10.0 out of 10, Exceptional, (53 reviews)
"A beautiful, well-kept cabin with plenty of amenities and meticulous surroundings... perfect for a quiet retreat. The owner was prompt in communicating when we had a couple of questions - very kind and friendly. Would definitely stay here again!!"
United States
Susan
$358 nightly
The price is $405
Oct 4 - Oct 5
Total with taxes and fees
Rustic Hideaway Sleeps 4 HOT TUB
A wooden deck with a bench, a white door, and hanging flower baskets.

14. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
$145 nightly
The price is $160
Oct 4 - Oct 5
Total with taxes and fees
The Bungaleau 1 Bedroom House In Cute Rivertown
A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

15. A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.8 out of 10, Exceptional, (138 reviews)
"The cottage was very quaint and comfortable. Great location for exploring downtown Mineral Point on foot. Had a fun stay."
United States
Rick C.
$225 nightly
The price is $248
Oct 4 - Oct 5
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Living area

16. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (123 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
$211 nightly
The price is $233
Oct 5 - Oct 6
Total with taxes and fees
Serenity Cottage at Mineral Point
A spacious living area with a wooden dining table, a sofa, and a hanging chair. There are large windows providing natural light and a view of the outside.

17. MJ's Penthouse ,a piece of paradise on Monroe's historic square

MJ's Penthouse ,a piece of paradise on Monroe's historic square
Monroe
10.0 out of 10, Exceptional, (111 reviews)
"The Penthouse is beautiful and the location is unbeatable! We had a wonderful stay and can't wait to come back."
United States
Andie
$248 nightly
The price is $272
Oct 1 - Oct 2
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

18. Your adventure begins the second you arrive!

Your adventure begins the second you arrive!
Norwalk
10.0 out of 10, Exceptional, (34 reviews)
"A great place to get away and relax."
United States
Betsy D.
$198 nightly
The price is $209
Oct 6 - Oct 7
Total with taxes and fees
Your adventure begins the second you arrive!
A living room with a sofa, two armchairs, a coffee table, and a large window with a view of trees.

19. RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife
Princeton
10.0 out of 10, Exceptional, (46 reviews)
"Cute property nicely located overlooking a beautiful marsh and river! Definitely recommend. Great value. Perfect for a couple. Recommended to host that window coverings be placed over picture window and patio door as well for privacy and security on riverside."
United States
Victoria J.
$221 nightly
The price is $233
Oct 1 - Oct 2
Total with taxes and fees
RiverFront Cottage>Private Pier>Firepit & Wildlife
A resort with multiple buildings, a golf course, and a large body of water in the background.

20. Golf or Summer Getaway@ Northern Bay Resort!

Golf or Summer Getaway@ Northern Bay Resort!
Arkdale
10.0 out of 10, Exceptional, (92 reviews)
"Nice location and nicely renovated"
United States
Tanner H.
$424 nightly
The price is $471
Oct 1 - Oct 2
Total with taxes and fees
Golf or Summer Getaway@ Northern Bay Resort!
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

AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

10/10 Excellent
"Clean, good breakfast"
John 2-night trip
Posted 2 hours ago
AmericInn by Wyndham Brookfield

Find out more about Southern Wisconsin

Everything you need to know about Southern Wisconsin vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Wisconsin vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Wisconsin vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Wisconsin vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Wisconsin. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southern Wisconsin in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southern Wisconsin rentals

At Expedia, we put the best Southern Wisconsin vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Wisconsin rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Wisconsin vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Wisconsin. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia