Holiday Homes in Southern Wisconsin

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Find holiday rentals that suit your style

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Cottages
Cottages

Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Southern Wisconsin holiday homes

A riverside view with a house and dense greenery.

1. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is AU$332
includes taxes & fees
9 Nov - 10 Nov
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
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, (182 reviews)
"Great stay and a wonderful property, look forward to staying again"
United States
Nate S.
The price is AU$234
includes taxes & fees
9 Nov - 10 Nov
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, (100 reviews)
"Nice stay, will stay again."
United States
Thomas D.
The price is AU$296
includes taxes & fees
15 Nov - 16 Nov
Ohio Street Retreat-hot tub, pool, massage chair
A rural landscape with a barn, a small house, and a large house with a porch.

4. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (49 reviews)
"Nice quiet getaway."
United States
RICHARD
The price is AU$182
includes taxes & fees
24 Nov - 25 Nov
Tamarack Point Homestead
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, (53 reviews)
"We had a wonderful stay! Loved the decor! Connie and Jim are wonderful hosts."
United States
Sara Z.
The price is AU$288
includes taxes & fees
10 Nov - 11 Nov
Gleason's Chouse
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

6. 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, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
The price is AU$214
includes taxes & fees
11 Nov - 12 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A house with a front porch, steps, and a small garden area.

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

Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
Kenosha
9.4 out of 10, Exceptional, (96 reviews)
"Comfy, cozy, and clean place to stay!!"
United States
Erin
The price is AU$113
includes taxes & fees
11 Nov - 12 Nov
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

8. 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, (34 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 AU$358
includes taxes & fees
21 Nov - 22 Nov
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Living area

9. Serenity Cottage at Mineral Point

Serenity Cottage at Mineral Point
Mineral Point
10.0 out of 10, Exceptional, (126 reviews)
"Super cute and cozy place - perfect for our getaway. "
United States
Katie K.
The price is AU$352
includes taxes & fees
1 Dec - 2 Dec
Serenity Cottage at Mineral Point
A modern kitchen with white cabinetry, a wooden table, a wicker basket, and a hanging light fixture.

10. 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, (8 reviews)
"Very clean and affordable. "
United States
Josh S.
The price is AU$493
includes taxes & fees
9 Nov - 10 Nov
Carefully curated and walkable to all Princeton has to offer.
A family standing in front of a stone building with a wooden porch and a number '816' above the entrance.

11. 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 AU$346
includes taxes & fees
9 Nov - 10 Nov
Hamilton Goebel House 816 E Louisa St Darlington Wi
A house with a paved driveway, surrounded by a wooded area.

12. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (73 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 AU$376
includes taxes & fees
10 Nov - 11 Nov
The Esker Ridge Chalet, Pristine Elkhart Solitude
A living room with a television, a coffee table, a sofa, and a dining area in the background.

13. 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, (32 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 AU$309
includes taxes & fees
9 Nov - 10 Nov
Hillsboro Driftless Guesthouse is cozy and ready for you!
A wooden deck with wicker furniture and a table, overlooking a forested area.

14. 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 AU$297
includes taxes & fees
17 Nov - 18 Nov
Remodeled, cozy, pet friendly cabin near lakes
A kitchen with wooden ceiling, white cabinets, a central island, a sink, a microwave, and a refrigerator.

15. Beautiful Lake House in County Park

Beautiful Lake House in County Park
West Bend
9.6 out of 10, Exceptional, (222 reviews)
"Great place! "
United States
Heather P.
The price is AU$554
includes taxes & fees
9 Nov - 10 Nov
Beautiful Lake House in County Park
A lakeside view with a gazebo, a round table, and a white picket fence.

16. Elegant Lake Home with Hot Tub

Elegant Lake Home with Hot Tub
Tomah
9.8 out of 10, Exceptional, (38 reviews)
"We loved our stay here! We would definitely book this house again if we come back to the area."
United States
Delila M.
The price is AU$581
includes taxes & fees
11 Nov - 12 Nov
Elegant Lake Home with Hot Tub
An outdoor deck with a table and four chairs, overlooking a body of water and surrounded by bare trees.

17. Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (66 reviews)
"Great place to stay for a weekend of fishing."
United States
Jason K.
The price is AU$425
includes taxes & fees
9 Nov - 10 Nov
Riverfront Twin Home
A breakfast setting with a table, chairs, plates, cutlery, glasses of orange juice, and a chocolate cake.

18. Downtown Spring Green Oasis | Hot Tub & Fire Pit

Downtown Spring Green Oasis | Hot Tub & Fire Pit
Spring Green
9.8 out of 10, Exceptional, (28 reviews)
"Kids loved all the board games and comfy seating options in the living room! Very comfortable stay."
United States
Elizabeth N.
The price is AU$449
includes taxes & fees
9 Nov - 10 Nov
Downtown Spring Green Oasis | Hot Tub & Fire Pit
A wooden deck with two rocking chairs overlooking a beach and a clear blue sky.

19. Margarita Villa | Lakefront | Beach | Game Room | 6 Bedrooms | 4 Bath

Margarita Villa | Lakefront | Beach | Game Room | 6 Bedrooms | 4 Bath
New Lisbon
10.0 out of 10, Exceptional, (17 reviews)
"Very clean and easy check in. Family friendly location with 2 paddleboards and 2 kayaks. I would suggest bringing extra beach towels and beach toys if applicable to your family."
United States
Katie F.
The price is AU$1,050
includes taxes & fees
15 Nov - 16 Nov
Margarita Villa | Lakefront | Beach | Game Room | 6 Bedrooms | 4 Bath
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.

20. 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, (115 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 AU$377
includes taxes & fees
9 Nov - 10 Nov
MJ's Penthouse ,a piece of paradise on Monroe's historic square
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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