Southwest Wisconsin Vacation Rentals

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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

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, (952)
"I love staying here."
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, (35)
"The perfect place to relax and enjoy quiet beauty. The kids loved the puzzles, I enjoyed the sunset and the sounds of Barred Owls. We’ll be back. "
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.
Exterior

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

9.6 out of 10, Exceptional, (16)
"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 $387
CA $511 total
includes taxes & fees
May 12 - May 13
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
Property grounds

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

9.8 out of 10, Exceptional, (22)
"Great. Thanks "
The price is CA $136
CA $188 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, (167)
"Very clean, comfortable and good location for getting around in Madison. Owners were attentive to answering any questions. Will definitely stay again."
Amazing townhouse, amazing attractions, amazing city!
Two bedroom suite with city views in the heart of downtown Madison
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (23)
"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 $456
CA $602 total
includes taxes & fees
May 12 - May 13
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, (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.
Exterior

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 CA $373
CA $493 total
includes taxes & fees
May 12 - May 13
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, (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!
Fridge, microwave, oven, stovetop

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
Exterior

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 $290
CA $382 total
includes taxes & fees
May 13 - May 14
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, (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
Exterior

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 CA $290
CA $704 total
includes taxes & fees
Apr 29 - Apr 30
Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells
River Front Property
Fridge, microwave, oven, stovetop

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
Fireplace

Riverfront Twin Home

10.0 out of 10, Exceptional, (22)
"Great place. Close to trails. Very clean. "
The price is CA $208
CA $456 total
includes taxes & fees
May 4 - May 5
Riverfront Twin Home
Romantic Get-a-Way!! 1954 Rail Road Caboose!! Relaxing Hot Tub!
Terrace/patio

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

9.8 out of 10, Exceptional, (477)
"Very nice well appointed and secluded get-away. Cozy cast iron stove took the spring chill off. It is well located for my adventure visiting a number of the state parks in SW Wisconsin."
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, (8)
"There was 7 of us who are teachers that were on Spring Break. We had a great time visiting the downtown area, visiting some establishments, enjoying adult beverages, and having adult conversations. The house was perfect. We enjoyed cooking breakfast in the beautiful kitchen, late night pizzas, and took our turns with the video games up in the game room. Recommend and if we get a chance we would book this house again. "
The price is CA $414
CA $924 total
includes taxes & fees
Apr 27 - Apr 28
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, (8)
"Nice place"
The price is CA $416
CA $1,146 total
includes taxes & fees
Apr 28 - Apr 29
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, (53)
"This property is super cute and the perfect spot! "
The price is CA $150
CA $258 total
includes taxes & fees
Apr 27 - Apr 28
Ohio Street Retreat-hot tub, massage chair, pool
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Exterior

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 CA $408
CA $800 total
includes taxes & fees
May 12 - May 13
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.
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Other property types in Southwest Wisconsin

The Dylin
Interior entrance

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (40)
"My stay was lovely. Everything was comfortable, clean and easy. I would recommend highly and absolutely be back to stay when visiting Madison again!"
The Dylin
Bluegreen Odyssey Dells
Water park

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
Indoor pool, seasonal outdoor pool

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.