A lighthouse and a house with a red roof.

Search Vacation Homes in Southern Wisconsin

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southern Wisconsin vacation homes

A field of lavender with a path leading through it.

1. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
The price is ￥14,396
￥18,519 total
includes taxes & fees
Oct 12 - Oct 13
Tamarack Point Homestead
A serene park with a pond, lush green grass, and a house in the background.

2. 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.
The price is ￥21,941
￥26,479 total
includes taxes & fees
Oct 6 - Oct 7
Country home with flowing river
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

3. Ohio Street Retreat-hot tub, pool, massage chair

Ohio Street Retreat-hot tub, pool, massage chair
Prairie du Chien
10.0 out of 10, Exceptional, (95 reviews)
"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"
United States
nate k.
The price is ￥18,753
￥33,831 total
includes taxes & fees
Nov 1 - Nov 2
Ohio Street Retreat-hot tub, pool, massage chair
A spacious, multi-level interior with a balcony, a laundry room, and various decorative items.

4. 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.
The price is ￥21,310
￥30,309 total
includes taxes & fees
Oct 7 - Oct 8
Gleason's Chouse
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

5. 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
9.8 out of 10, Exceptional, (32 reviews)
"A lovely location, and the lodging was quite comfortable and enjoyable to spend time in. We hope to be able to return."
United States
Mike G.
The price is ￥20,521
￥39,417 total
includes taxes & fees
Oct 18 - Oct 19
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
A kitchen with a sliding glass door leading to a wooden deck with a view of a grassy field and a lake.

6. Updated home with lake views, across the street from Lake WI, near free ferry

Updated home with lake views, across the street from Lake WI, near free ferry
Merrimac
10.0 out of 10, Exceptional, (44 reviews)
"Very clean property, exactly as advertised. Host was easy to work with."
United States
Jacob M.
The price is ￥28,255
￥53,629 total
includes taxes & fees
Oct 14 - Oct 15
Updated home with lake views, across the street from Lake WI, near free ferry
Living area

7. 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.
The price is ￥24,293
￥36,788 total
includes taxes & fees
Oct 12 - Oct 13
Serenity Cottage at Mineral Point
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

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

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥22,730
￥27,311 total
includes taxes & fees
Oct 7 - Oct 8
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A cabin with a deck, a covered porch, and a paved driveway.

9. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (71 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is ￥31,412
￥42,799 total
includes taxes & fees
Oct 6 - Oct 7
The Esker Ridge Chalet, Pristine Elkhart Solitude
Property grounds

10. Remodeled, cozy, pet friendly cabin near lakes

Remodeled, cozy, pet friendly cabin near lakes
Necedah
10.0 out of 10, Exceptional, (39 reviews)
"This is a cute little place out in the country. Communication with the hostess was good."
United States
Dawn
The price is ￥14,996
￥36,639 total
includes taxes & fees
Oct 7 - Oct 8
Remodeled, cozy, pet friendly cabin near lakes
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

11. Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Northside
9.8 out of 10, Exceptional, (68 reviews)
"I"
United States
Charlie
The price is ￥17,364
￥29,045 total
includes taxes & fees
Oct 18 - Oct 19
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A wooden deck with a bench, a white door, and hanging flower baskets.

12. 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.
The price is ￥19,747
￥25,311 total
includes taxes & fees
Oct 19 - Oct 20
The Bungaleau 1 Bedroom House In Cute Rivertown
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

13. Hamilton Goebel House 816 E Louisa St Darlington Wi

Hamilton Goebel House 816 E Louisa St Darlington Wi
Darlington
9.8 out of 10, Exceptional, (54 reviews)
"Three couples stayed at this property. Very comfy beds. We all enjoyed our stay and already have plans to stay again in the fall. It is also close to the trails."
United States
Danette M.
The price is ￥16,195
￥40,030 total
includes taxes & fees
Oct 6 - Oct 7
Hamilton Goebel House 816 E Louisa St Darlington Wi
A modern kitchen with white cabinetry, a wooden table, a wicker basket, and a hanging light fixture.

14. Carefully curated and walkable to all Princeton has to offer.

Carefully curated and walkable to all Princeton has to offer.
Princeton
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and affordable. "
United States
Josh S.
The price is ￥31,728
￥57,289 total
includes taxes & fees
Oct 6 - Oct 7
Carefully curated and walkable to all Princeton has to offer.
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.

15. 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
The price is ￥30,781
￥43,385 total
includes taxes & fees
Oct 7 - Oct 8
MJ's Penthouse ,a piece of paradise on Monroe's historic square
A living room with a television, a coffee table, a sofa, and a dining area in the background.

16. 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, (31 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
The price is ￥20,315
￥33,923 total
includes taxes & fees
Oct 7 - Oct 8
Hillsboro Driftless Guesthouse is cozy and ready for you!
A single-story house with a front porch, a garage, and a small shed in a grassy yard surrounded by trees.

17. Fawn Lake Cottage for Families Looking for Privacy

Fawn Lake Cottage for Families Looking for Privacy
Wisconsin Dells
9.8 out of 10, Exceptional, (11 reviews)
"Great home and host beautiful home "
United States
Michael C.
The price is ￥16,890
￥53,937 total
includes taxes & fees
Oct 6 - Oct 7
Fawn Lake Cottage for Families Looking for Privacy
A covered outdoor area with a table and chairs, a view of a lake, and docked boats.

18. Dells Lake Villa - Lake Front Luxury

Dells Lake Villa - Lake Front Luxury
Lake Delton
9.6 out of 10, Exceptional, (14 reviews)
"Nice property and close to many of the Dells attractions."
United States
Mark V.
The price is ￥27,093
￥63,485 total
includes taxes & fees
Oct 18 - Oct 19
Dells Lake Villa - Lake Front Luxury
A serene lakeside setting with a wooden dock extending into the water, surrounded by lush greenery and trees.

19. Lake Cottage 30 minutes from Wisconsin Dells.

Lake Cottage 30 minutes from Wisconsin Dells.
Friendship
9.8 out of 10, Exceptional, (62 reviews)
"The whole process from rental to leaving was simple. Loved the two docks available to fish from (front and rear of the cottage). Husband loved that there was kayaks , canoe l, and row boat available to get out on the lake. Home was very inviting and home like. Would definitely stay again!"
United States
Rebecca L.
The price is ￥16,574
￥48,296 total
includes taxes & fees
Oct 8 - Oct 9
Lake Cottage 30 minutes from Wisconsin Dells.
A deck with a glass table and chairs, a barbecue grill, and an umbrella.

20. 2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley

2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley
Adams
9.6 out of 10, Exceptional, (24 reviews)
"It was a beautiful house, we enjoyed our stay! Comfortably accommodated 10 people. "
United States
Stephanie G.
The price is ￥17,048
￥53,792 total
includes taxes & fees
Oct 8 - Oct 9
2400 sqft Spacious Luxury Value. 30 min from Wis Dells. 20 Min to Sand Valley
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

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

10/10 Excellent
"1"
Brian 2-night trip
Posted 1 hour ago
Mt. Olympus Water & Theme Park Resort

Find out more about Southern Wisconsin

Southern Wisconsin Vacation Homes information

Number of reviews
1,215
Accommodation
683 Vacation Homes
Lowest Price
￥18,519
Highest Price
￥57,289

Explore a world of travel with Expedia