Southwest Wisconsin Vacation Rentals

April 2025

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Southwest Wisconsin Vacation Homes

Tamarack Wisconsin Dells a Ramada by Wyndham
Indoor pool, seasonal outdoor pool

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (947)
"If your Ever in Wisconson this is where you want to stay ! You be very comfortable with your stay ! Also it’s family friendly "
Tamarack Wisconsin Dells a Ramada by Wyndham
Elegant country retreat near Spring Green w expansive views of Driftless Region
Smart TV, DVD player, books

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

10.0 out of 10, Exceptional, (33)
"Perfect place for a family getaway - two busy working parents, our combined four kids. Peaceful, but easy access to local towns for what we needed. Barbara was responsive and we loved the home. Truly a little oasis!"
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.
Aerial view

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

9.6 out of 10, Exceptional, (15)
"Our family stayed at The Saddlery hotel to celebrate our son's birthday, who is a freshman at the UW Madison.We absolutely loved everything about this hotel. From the efficient check in/check out process, very clean and beautiful rooms, amazing Lake Monona view, each moment was delightful. Also the hotel has a very safe and secure environment. The only thing that I dislike was that 20 minutes before the check out the cleaning staff was knocking on the door and came inside. I think they should...
The price is CA $330
CA $436 total
includes taxes & fees
Apr 3 - Apr 4
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Charming 2-bedroom house close to airport and downtown with many amenities
Microwave, oven

Charming 2-bedroom house close to airport and downtown with many amenities

"The home is super cute and the owners were very quick to respond to questions. I would definitely stay again "
The price is CA $230
CA $329 total
includes taxes & fees
Apr 3 - Apr 4
Charming 2-bedroom house close to airport and downtown with many amenities
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Property grounds

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

9.6 out of 10, Exceptional, (18)
"This home was very cute and cozy. Decor was very cool. Communication was great! Would definitely stay here again. "
The price is CA $140
CA $194 total
includes taxes & fees
Apr 29 - Apr 30
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Amazing townhouse, amazing attractions, amazing city!
Fridge, microwave, oven, stovetop

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (165)
"The property is cleaned and organized. It fits well for a small family. The checkin checkout process is convenient. We are satisfied."
Amazing townhouse, amazing attractions, amazing city!
Two bedroom suite with city views in the heart of downtown Madison
Aerial view

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

10.0 out of 10, Exceptional, (21)
"Second time staying here. Love to neighborhood. Easy to walk to restaurants bars shopping. View of the lake is beautiful. Can’t wait for warm weather to enjoy to 3rd floor patio!"
The price is CA $416
CA $549 total
includes taxes & fees
Apr 6 - Apr 7
Two bedroom suite with city views in the heart of downtown Madison
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
Outdoor spa tub

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

10.0 out of 10, Exceptional, (152)
"Perfect"
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
One Bedroom King with Den with views of the heart of downtown.
Aerial view

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"Great spot…close to the city center. Plenty of restaurants, and a sweet music venue in The Majestic. We will be back!"
The price is CA $315
CA $417 total
includes taxes & fees
Apr 3 - Apr 4
One Bedroom King with Den with views of the heart of downtown.
A Pleasant Retreat- No Cleaning Fee & New Discounts
Exterior

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (230)
"Girls weekend with 3 of us. We each had our own room. The Frank Lloyd Wright inspired décor and the Georgia O'Keefe artwork was great. The hosts are friendly and made sure we had everything we needed at check in. Fresh flowers on the table were a nice touch. We would definitely stay there again."
A Pleasant Retreat- No Cleaning Fee & New Discounts
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.6 out of 10, Exceptional, (13)
"Property was clean and laid out nicely. Beds were very comfortable! Kitchen was nice and very functional. Location was great as it’s close to our daughter and son in laws home. Michelle was very responsive to questions and care package was a nice touch coming into the living space! Perfect size for 2-3 people. Our dogs enjoyed as well! Thank you Michelle!"
Paoli Den - Newly Remodeled!
Studio queen with views of Lake Monona in the heart of downtown Madison
Aerial view

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

9.2 out of 10, Wonderful, (5)
"We had no issues with our stay and really enjoyed the unit we booked. "
The price is CA $229
CA $303 total
includes taxes & fees
Apr 3 - Apr 4
Studio queen with views of Lake Monona in the heart of downtown Madison
Downtown Baraboo Blu-Mae Marie Folk House
Exterior

Downtown Baraboo Blu-Mae Marie Folk House

9.8 out of 10, Exceptional, (80)
"Had a Wonderful stay! Close to the middle of town! Perf"
Downtown Baraboo Blu-Mae Marie Folk House
Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells
Exterior

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

9.8 out of 10, Exceptional, (104)
"Stayed the weekend to ski at Cascade Mountain. House was clean, comfortable, well-appointed. We had plenty of room for 3 families with little kids. Ashley was extremely responsive and even mailed me something I had left behind. Definitely recommend!"
The price is CA $315
CA $751 total
includes taxes & fees
Apr 6 - Apr 7
Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells
River Front Property
Smart TV, video games, books, stereo

River Front Property

10.0 out of 10, Exceptional, (85)
"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
Property grounds

Riverfront Twin Home

10.0 out of 10, Exceptional, (20)
"Very clean. Great location. Well stocked kitchen. Very comfortable beds. Lots of walking trails nearby. Had a wonderful weekend. "
The price is CA $214
CA $468 total
includes taxes & fees
Apr 15 - Apr 16
Riverfront Twin Home
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
Property grounds

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

9.8 out of 10, Exceptional, (473)
"Had a great time here. Had everything we needed. I loved how secluded it was. A perfect getaway! We really enjoyed the hot tub. The owner was very thoughtful and left us a giftcard to a nearby restaurant and some wine and waters in the fridge. Would definitely stay here again!"
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
The Downtowner-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court
Terrace/patio

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

2.0 star property
9.8 out of 10, Exceptional, (7)
"Convenient location, nice house"
The price is CA $427
CA $961 total
includes taxes & fees
Apr 15 - Apr 16
The Downtowner-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
Fridge, microwave, oven, stovetop

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Nice place"
The price is CA $466
CA $1,244 total
includes taxes & fees
Apr 30 - May 1
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
Ohio Street Retreat-hot tub, massage chair, pool
Interior

Ohio Street Retreat-hot tub, massage chair, pool

10.0 out of 10, Exceptional, (51)
"very clean nice little house, perfect for a family visit"
The price is CA $208
CA $331 total
includes taxes & fees
Apr 15 - Apr 16
Ohio Street Retreat-hot tub, massage chair, pool
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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Other property types in Southwest Wisconsin

The Dylin
Interior entrance

The Dylin

4.0 star property
9.6 out of 10, Exceptional, (27)
"Great location and very clean "
The price is CA $123
CA $143 total
includes taxes & fees
Apr 6 - Apr 7
The Dylin
Bluegreen Vacations Odyssey Dells Resort
Water park

Bluegreen Vacations Odyssey Dells Resort

3.5 star property
9.4 out of 10, Exceptional, (103)
"I would highly recommend staying here. Great value and the rooms were spacious, clean and quiet. Right in the perfect spot in the dells and next to Mt Olympus! It has a connection inside to get to the waterpark and theme park so you don't have to walk outside"
Bluegreen Vacations Odyssey Dells Resort
Tamarack Wisconsin Dells a Ramada by Wyndham
Indoor pool, seasonal outdoor pool

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (947)
"If your Ever in Wisconson this is where you want to stay ! You be very comfortable with your stay ! Also it’s family friendly "
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.