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Next weekend
14 Nov - 16 Nov
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21 Nov - 23 Nov
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5 Dec - 7 Dec
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Featured Cottages in Southwest Wisconsin

Exterior
Tiny House on the River

Tiny House on the River

Black River Falls
10.0 out of 10, Exceptional, (77)
"It was so amazing! Very clean and so cozy and we loved it in summer but want to come back for winter. "
United States
Taylor T.
The price is NZ$381
includes taxes & fees
11 Nov - 12 Nov
Tiny House on the River
Property grounds
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!

2.0 star property
Milton
9.4 out of 10, Exceptional, (3)
"Confusion at check in that appeared to be a mis-communication by Vrbo. Owners were very responsive and very accommodating. Pictures showed larger couch that we planned to use as additional bed but all worked out without it"
United States
Kelly R.
The price is NZ$276
includes taxes & fees
11 Nov - 12 Nov
Charming 2-bedroom cottage near Lake Koshkonong - The Overlook Too!
Smart TV
RiverFront Cottage>Private Pier>Firepit & Wildlife

RiverFront Cottage>Private Pier>Firepit & Wildlife

Princeton
10.0 out of 10, Exceptional, (40)
"Beautiful place, definitely gives a cozy vibes. Good location. We had a wonderful stay, we will definitely book here again in the future. "
United States
Megan G.
The price is NZ$406
includes taxes & fees
12 Nov - 13 Nov
RiverFront Cottage>Private Pier>Firepit & Wildlife
Exterior
A Comfy Cozy Cottage on Clowney

A Comfy Cozy Cottage on Clowney

Mineral Point
9.6 out of 10, Exceptional, (117)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is NZ$371
includes taxes & fees
10 Nov - 11 Nov
A Comfy Cozy Cottage on Clowney
Exterior
Walleye Waters Cottage

Walleye Waters Cottage

Briggsville
10.0 out of 10, Exceptional, (6)
"Everything was clean and the stress was very cute. Only a short drive to the dells"
United States
Sarah C.
The price is NZ$427
includes taxes & fees
10 Nov - 11 Nov
Walleye Waters Cottage
Property grounds
Fall on the lake: hot tub, firepit & cozy nights

Fall on the lake: hot tub, firepit & cozy nights

Wild Rose
10.0 out of 10, Exceptional, (13)
"This was a great getaway for spring break with my kids and a friend. Despite it being cold we enjoyed kayaking and relaxing in the hot tub. Very peaceful! Definitely would book again in the summer!"
United States
Mikko H.
Fall on the lake: hot tub, firepit & cozy nights
Exterior
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park

Bagley
9.6 out of 10, Exceptional, (37)
"We really enjoyed our stay!"
Netherlands
Constance S.
The price is NZ$567
includes taxes & fees
11 Nov - 12 Nov
Cozy Cottage getaway on the Mississippi/Wisconsin River in Wyalusing State Park
Terrace/patio
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells

Wisconsin Dells
10.0 out of 10, Exceptional, (9)
"We had a great day at the 10 Fox. They thought of many of the things one might need with small kids. It was really great to have a house outside of town, but also not that far making it very convenient to pop into town. Molly was very responsive to the few questions we had. "
United States
Alicia W.
The price is NZ$652
includes taxes & fees
13 Nov - 14 Nov
Newly Remodeled 3BR Cottage w/ Hot Tub - Fire Pit - Near Wisconsin Dells
Exterior
Cozy Riverfront Cottage w/ Kayaks & Fire Pit – Near Madison & Milwaukee

Cozy Riverfront Cottage w/ Kayaks & Fire Pit – Near Madison & Milwaukee

2.0 star property
Johnson Creek
The price is NZ$272
includes taxes & fees
18 Nov - 19 Nov
Cozy Riverfront Cottage w/ Kayaks & Fire Pit – Near Madison & Milwaukee
Exterior
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Lyndon Station
9.8 out of 10, Exceptional, (36)
"Great place for family to reconnect with each other ❤️"
United States
Christine A.
The price is NZ$684
includes taxes & fees
10 Nov - 11 Nov
Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!
Exterior
Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries

Merrimac
8.0 out of 10, Very good, (1)
"Owner accidently gave us the wrong door code, but mistakes happen and we problem solved.Inside was even nicer & updated from photos shown overall and the space was perfect for what we needed.I do not believe the description was fully complete. It said Bluff Views which I didn't see which was fine, but I was NOT expecting this tiny house to be in a parking lot adjacent of a bar/venue. The one photo of the ouside is clearly photoshopped into blue sky, but it is really a blue bar.Our stay was...
United States
Sheri M.
The price is NZ$434
includes taxes & fees
19 Nov - 20 Nov
Charming cottage in lovely Merrimac next to Ski/Golf/Hiking/Breweries
Exterior
Charming A-Frame Cottage, HOT TUB, Fire Pit, Near GOLF & Lakes, 35min to Dells!

Charming A-Frame Cottage, HOT TUB, Fire Pit, Near GOLF & Lakes, 35min to Dells!

Friendship
10.0 out of 10, Exceptional, (2)
"My entire family loved the house. First impression was adorable and welcoming. I have kids that range 11-17 and they all enjoyed inside and out. The hot tub was definitely a hit. We enjoyed the fire pit and bags every day. The quiet space inside and out was perfect! You have made a great space and we would highly recommend this place to anyone!"
United States
christian g.
The price is NZ$751
includes taxes & fees
12 Nov - 13 Nov
Charming A-Frame Cottage, HOT TUB, Fire Pit, Near GOLF & Lakes, 35min to Dells!
Terrace/patio
Charming Nekoosa Home with Lake access

Charming Nekoosa Home with Lake access

Nekoosa
10.0 out of 10, Exceptional, (5)
"Great spot to stay with friends close to sand valley. Plenty of space for our group and a very nice set up. "
United States
Justin L.
The price is NZ$918
includes taxes & fees
10 Nov - 11 Nov
Charming Nekoosa Home with Lake access
Exterior
Mississippi River Front Property with amazing views!

Mississippi River Front Property with amazing views!

Harpers Ferry
9.0 out of 10, Wonderful, (12)
"The property was exactly what we were looking for during our fall weekend gateway. We enjoyed the exceptional view of the Mississippi in the morning. And the hot tub at night. Great and easy communication with the property manager. We would come back again in a heart beat. "
United States
gwen l.
Mississippi River Front Property with amazing views!
House (3 Bedrooms) | Interior
'the Fiveten Federal' - Downtown Galena Gem!

'the Fiveten Federal' - Downtown Galena Gem!

3.0 star property
Galena
'the Fiveten Federal' - Downtown Galena Gem!
Family Cottage, Park View | Terrace/patio
Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow

3.0 star property
Winona
The price is NZ$432
includes taxes & fees
11 Nov - 12 Nov
Big River Escape Parkside Bungalow
Exterior
Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Relaxing Taylor Lake Retreat directly on the Chain of Lakes

Chain O' Lakes
9.0 out of 10, Wonderful, (22)
"Beautiful place on the lake. We enjoyed staying here."
United States
Jacquelyn L.
The price is NZ$607
includes taxes & fees
10 Nov - 11 Nov
Relaxing Taylor Lake Retreat directly on the Chain of Lakes
Exterior
Cozy cottage on the Fox River, in town location

Cozy cottage on the Fox River, in town location

Omro
10.0 out of 10, Exceptional, (3)
"Loved the location! We had some activities planned in Oshkosh and it's an easy, convenient drive. The cottage itself was comfortable for us. Ammenities are as described. Scenic backyard on the Fox River. "
United States
Tracy S.
The price is NZ$446
includes taxes & fees
10 Nov - 11 Nov
Cozy cottage on the Fox River, in town location
Property grounds
Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.

Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.

Cherry Valley
9.8 out of 10, Exceptional, (11)
The price is NZ$386
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.
Outdoor dining
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access

Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access

The Galena Territory
10.0 out of 10, Exceptional, (13)
"The cottage itself was great! It is a bit out of the way- It is also an HOA with many amenities, but they are miles away. We had some trouble navigating where to find the needed parking pass to utilize the amenities. The cottage is nestled among several other little cottages. Nice place, Galena is a lot of fun with very kind people!"
United States
Amy R.
The price is NZ$544
includes taxes & fees
10 Nov - 11 Nov
Charming & Cozy 2BR Cottage | Fireplace | Dog-Friendly | Amenity Access
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 Southwest Wisconsin Hotel Reviews

Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

10/10 Excellent
"The staff are always courteous. "
Sonya 2-night trip
Posted 4 days ago
Days Inn & Suites by Wyndham Wisconsin Dells

Find out more about Southwest Wisconsin

Southwest Wisconsin Cottages information

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Frequently asked questions

How much do cottages in Southwest Wisconsin cost?
Cottages in Southwest Wisconsin range between and per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southwest Wisconsin?
Southwest Wisconsin has cottages to choose from. Select your travel dates, enter your destination and plan your next escape today.
What is there to do in Southwest Wisconsin near my cottage?
Whether you enjoy shopping, dining, history or culture, Southwest Wisconsin offers something for everyone! The well-known city of Wisconsin Dells boasts loads of things to do, including Rick Wilcox Magic Theatre, Noah's Ark Waterpark and Timbavati Wildlife Park. If you're escaping to La Crosse, Pettibone Park, Swarthout Museum and Grandad Bluff Park should be on your to-do list.

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