Southern Wisconsin Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Southern Wisconsin vacation rentals

Property grounds

Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (33 reviews)
"It is a lovely spot. Very relaxing. "
United States
Peggy K.
$111 nightly
The price is $117
Jan 25 - Jan 26
Total with taxes and fees
Tamarack Point Homestead
Smart TV

Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center

Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center
Richland Center
10.0 out of 10, Exceptional, (33 reviews)
"The hunters really enjoyed their stay. "
United States
Rhoda H.
$155 nightly
The price is $164
Jan 25 - Jan 26
Total with taxes and fees
Charming secluded 2-bedroom cabin with WiFi, AC in peaceful Richland Center
Property grounds

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.6 out of 10, Exceptional, (87 reviews)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
$97 nightly
The price is $110
Jan 28 - Jan 29
Total with taxes and fees
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Exterior

Beautiful Lakefront Home ~ Outstanding Sunsets ~ Includes Hot Tub!

Beautiful Lakefront Home ~ Outstanding Sunsets ~ Includes Hot Tub!
Winneconne
9.6 out of 10, Exceptional, (382 reviews)
"We thoroughly enjoyed our long weekend stay. The home had everything we needed. It is a lovely home, nicely decorated, with a great location on the lake. "
United States
Mary M.
$241 nightly
The price is $253
Jan 25 - Jan 26
Total with taxes and fees
Beautiful Lakefront Home ~ Outstanding Sunsets ~ Includes Hot Tub!
Smart TV

RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife
Princeton
10.0 out of 10, Exceptional, (40 reviews)
"We loved this quiet getaway! Simply perfect and simple. Great sunsets and rainbows! "
United States
Kevin
$200 nightly
The price is $211
Jan 27 - Jan 28
Total with taxes and fees
RiverFront Cottage>Private Pier>Firepit & Wildlife
View from property

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, (47 reviews)
"The staff was great and i enjoyed the entire stay."
United States
Wakeem
$139 nightly
The price is $152
Jan 26 - Jan 27
Total with taxes and fees
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
Interior

A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney
Mineral Point
9.6 out of 10, Exceptional, (119 reviews)
"Comfortable, easy stay for a weekend. "
United States
Kelly
$225 nightly
The price is $248
Jan 25 - Jan 26
Total with taxes and fees
A Comfy Cozy Cottage on Clowney
Terrace/patio

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (65 reviews)
"Clean, pet friendly, great location"
United States
Matthew K.
$244 nightly
The price is $257
Jan 25 - Jan 26
Total with taxes and fees
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Property grounds

Log Cabin at Lake Koshkonong - “The Overlook”

Log Cabin at Lake Koshkonong - “The Overlook”
Edgerton
9.2 out of 10, Wonderful, (48 reviews)
"Such a cute cabin across the street from Lake Koshkonong. Our host was very accommodating and quick to respond!"
United States
John & Debbie R.
$154 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Log Cabin at Lake Koshkonong - “The Overlook”
Fridge, microwave, oven, stovetop

Ohio Street Retreat-hot tub, massage chair, pool

Ohio Street Retreat-hot tub, massage chair, pool
Prairie du Chien
10.0 out of 10, Exceptional, (77 reviews)
"Great stay overall."
United States
Keelie D.
$197 nightly
The price is $207
Jan 25 - Jan 26
Total with taxes and fees
Ohio Street Retreat-hot tub, massage chair, pool
Smart TV, DVD player

Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (26 reviews)
"The home was extremely clean, decorated nicely, very homey, had everything we needed and more! We can’t wait to return!"
United States
Brett B.
$186 nightly
The price is $196
Jan 26 - Jan 27
Total with taxes and fees
Hillsboro Driftless Guesthouse is cozy and ready for you!
Interior

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, (102 reviews)
"Such a fun place to stay! We loved it!"
United States
Karen J.
$240 nightly
The price is $263
Jan 25 - Jan 26
Total with taxes and fees
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (123 reviews)
"Great stay at the Dylin"
United States
Lauri
$107 nightly
The price is $124
Jan 26 - Jan 27
Total with taxes and fees
The Dylin
Exterior

River Road Retreat

River Road Retreat
Muscoda
9.6 out of 10, Exceptional, (24 reviews)
"Wonderful place to stay. Hosts were amazing."
United States
Mary M.
$226 nightly
The price is $238
Jan 25 - Jan 26
Total with taxes and fees
River Road Retreat
1 bedroom, desk, free WiFi, bed sheets

Quaint cabin overlooking the creek below and wetlands in the valley basin.

Quaint cabin overlooking the creek below and wetlands in the valley basin.
Norwalk
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful relaxing getaway!"
United States
Amanda M.
$277 nightly
The price is $292
Jan 25 - Jan 26
Total with taxes and fees
Quaint cabin overlooking the creek below and wetlands in the valley basin.
Exterior

Rustic Hideaway Sleeps 4 HOT TUB

Rustic Hideaway Sleeps 4 HOT TUB
De Soto
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful area, the house was very clean and had everything you needed to cook with! We loved our stay!"
United States
Sarah L.
$337 nightly
The price is $382
Jan 25 - Jan 26
Total with taxes and fees
Rustic Hideaway Sleeps 4 HOT TUB
1 bedroom, iron/ironing board, free WiFi, bed sheets

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
10.0 out of 10, Exceptional, (20 reviews)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
$186 nightly
The price is $211
Jan 25 - Jan 26
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Fridge, microwave, oven, stovetop

Great 1 Bedroom unit with easy access to everything

Great 1 Bedroom unit with easy access to everything
Lower Northside
9.6 out of 10, Exceptional, (53 reviews)
"We had a great time! The house was clean and comfortable, and the dining options nearby were fantastic. The house was centrally located to what we wanted to do around town, so it made a great place to stay! Thank you for the wonderful time. "
United States
Dylan R.
$220 nightly
The price is $253
Jan 25 - Jan 26
Total with taxes and fees
Great 1 Bedroom unit with easy access to everything
Beach

Lake Geneva - Fireplace - Pool - Fast WiFi

Lake Geneva - Fireplace - Pool - Fast WiFi
Lake Geneva
10.0 out of 10, Exceptional, (36 reviews)
"Great little spot. Close distance to water, good restaurants and shopping. Nicole was a wonderful host and communicated early and often. We had a fantastic time!"
United States
Gregg K.
$223 nightly
The price is $248
Jan 26 - Jan 27
Total with taxes and fees
Lake Geneva - Fireplace - Pool - Fast WiFi
Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,018 reviews)
"Great start!! Will be back!"
United States
Venir
$109 nightly
The price is $124
Jan 25 - Jan 26
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
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.
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Top Southern Wisconsin Hotel Reviews

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

10/10 Excellent
"Easy"
Mike 1-night trip
Posted 1 day ago
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

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 $124 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.

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