Search Vacation Homes in Southwest Wisconsin

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Compare 673 Vacation Homes in Southwest Wisconsin with updated reviews, rates, and availability.

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (952)
"I love staying here."
Tamarack Wisconsin Dells a Ramada by Wyndham

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (36)
"The Glass House is the perfect place to relax and unwind. The house itself is cozy and is stocked with the necessities. Easy check-in/check-out process and great communication from the host. The property around the house is incredible, plenty of walking trails to enjoy. It feels like your own private wildlife sanctuary. Perfect location if you enjoy birding and wildlife."
Elegant country retreat near Spring Green w expansive views of Driftless Region

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.6 out of 10, Exceptional, (19)
"The manager was very responsive and timely. Allowed us to store our luggage before check-in. Accommodations were clean and comfortable."
The price is SAR 1,047
SAR 1,382 total
includes taxes & fees
15 May - 16 May
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

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

9.8 out of 10, Exceptional, (24)
"Great communication! Super price for the area. We've stayed her two times now for a sport's tournament and it was the perfect place to relax each evening. Clean, cute, had everything we needed and much better than staying in a noisy hotel with the rest of the team :) The owners are great--super friendly too! "
The price is SAR 368
SAR 509 total
includes taxes & fees
30 Apr - 1 May
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (168)
"Everything was very clean, amenities were awesome and overall we had a great time! "
Amazing townhouse, amazing attractions, amazing city!

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (26)
"Everything was great. We could have used more comfy furniture. With 4 people and just a couch, it wasn’t idea for hanging out. Maybe just another big comfy chair or love seat."
The price is SAR 1,234
SAR 1,629 total
includes taxes & fees
14 May - 15 May
Two bedroom suite with city views in the heart of downtown Madison

Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.

10.0 out of 10, Exceptional, (156)
"It's a very nice cabin up on top of a hill in Independence, Wisconsin and we had a lovely time here! Very nice hot tub, lots of space to relax in, and the owners left little treats like cupcakes, chocolates, and non-slip socks for everyone! Definitely enjoyed our time here, likely to come back again!"
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (10)
"'Twas a very nice stay .Wife,son 2 dogs and myself .Good location except for the work being done on the street . Walking distance to restaurants and attractions. "
The price is SAR 1,009
SAR 1,334 total
includes taxes & fees
14 May - 15 May
One Bedroom King with Den with views of the heart of downtown.

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (233)
"This home was perfect for our family and was so cute and clean. But the owners are what made it so special. They greeted us and showed us around the house. They made sure you felt at home. "
A Pleasant Retreat- No Cleaning Fee & New Discounts

Paoli Den - Newly Remodeled!

9.6 out of 10, Exceptional, (15)
"Cute and clean lower level apartment that had everything we needed. The host was extremely responsive and added personal touches to make us feel welcomed. There are some stairs to navigate and other tenants in the building, but we had no problems. "
Paoli Den - Newly Remodeled!

Studio queen with views of Lake Monona in the heart of downtown Madison

9.4 out of 10, Exceptional, (6)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is SAR 784
SAR 1,036 total
includes taxes & fees
14 May - 15 May
Studio queen with views of Lake Monona in the heart of downtown Madison

Downtown Baraboo Blu-Mae Marie Folk House

9.8 out of 10, Exceptional, (82)
"We loved the area and it was not far to travel to the places we e attended "
Downtown Baraboo Blu-Mae Marie Folk House

Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells

9.8 out of 10, Exceptional, (106)
"Super clean, convenient location, many thoughtful amenities. Two bathrooms may be tough for a larger group, but our group of 5 fit perfectly. Would definitely recommend! "
The price is SAR 822
SAR 1,957 total
includes taxes & fees
30 Apr - 1 May
Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells

River Front Property

10.0 out of 10, Exceptional, (87)
"We stayed at a wonderful Vrbo right on the river. It was a beautiful 3 bedroom flat with a 4 season room and a large deck. It had a stairway down to a fishing pier. We got there and it was 80 degrees. Beautiful fishing weather. We caught some walleye and perch. The next day the weather was horrrible. We couldn’t fish much but enjoyed the rental immensely. It is great for fishing, relaxing and so much more!! "
River Front Property

Riverfront Twin Home

10.0 out of 10, Exceptional, (22)
"Great place. Close to trails. Very clean. "
The price is SAR 563
SAR 1,234 total
includes taxes & fees
7 May - 8 May
Riverfront Twin Home

Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

9.8 out of 10, Exceptional, (478)
"We enjoyed a weekend at this cozy, well-appointed caboose. The hot tub gazebo was delightful and owner John was quick to respond to questions and requests. "
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!

The Downtowner-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court

2.0 star property
9.8 out of 10, Exceptional, (10)
"We had a mix of adults and children and loved our stay! The house is walking distance to downtown, but also had plenty of space if you stay inside! The kids loved the playroom and the adults hung around the kitchen island. We didn’t get to take advantage of the outside area due to weather but the porch and yard are beautiful.We are already talking about going back!"
The price is SAR 1,122
SAR 2,501 total
includes taxes & fees
30 Apr - 1 May
The Downtowner-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court

Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

2.0 star property
10.0 out of 10, Exceptional, (8)
"Nice place"
The price is SAR 1,497
SAR 3,575 total
includes taxes & fees
30 Apr - 1 May
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

Ohio Street Retreat-hot tub, massage chair, pool

10.0 out of 10, Exceptional, (54)
"This property is super cute and the perfect spot! "
The price is SAR 405
SAR 699 total
includes taxes & fees
30 Apr - 1 May
Ohio Street Retreat-hot tub, massage chair, pool

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (34)
"We came into town for a girls weekend with our students at UW Madison. We had a fantastic stay here. The property was spotless. The views were beautiful. Our girls stayed with us. The location is perfect and easy to Uber from downtown Madison. A very safe and quiet location. We will definitely stay here again when we come back into town."
The price is SAR 1,106
SAR 2,158 total
includes taxes & fees
14 May - 15 May
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
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.
Don't see what you're looking for?
See all available properties in Southwest Wisconsin
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southwest Wisconsin

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (40)
"Very new & clean, nice lobby and outdoor area in a good location, walkable to most of Madison."
The price is SAR 469
SAR 542 total
includes taxes & fees
26 May - 27 May
The Dylin

Bluegreen Odyssey Dells

3.5 star property
9.4 out of 10, Exceptional, (115)
"Excellent customer service and clean room"
Bluegreen Odyssey Dells

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (952)
"I love staying here."
Tamarack Wisconsin Dells a Ramada by Wyndham
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.