Southwest Wisconsin Vacation Rentals

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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, (37)
"Serene beautiful location Close to everything we wanted to do in area Perfect short stay"
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, (19)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is CA $385
CA $508 total
includes taxes & fees
May 14 - May 15
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, (24)
"This was a great place to stay that was close to UWL and downtown. Loved having the room to move around in the house vs a hotel room. Also, loved the outdoor area. "
The price is CA $135
CA $187 total
includes taxes & fees
May 12 - May 13
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, (168)
"The place was nice and clean. Perfect place for a book weekend!"
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

9.8 out of 10, Exceptional, (26)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is CA $454
CA $599 total
includes taxes & fees
May 14 - May 15
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, (157)
"The place exceeded all expectations, and was even better than the pictures. Kelli was so accommodating, and we felt so comfortable know that if we needed anything at all she'd be more than willing to help! Looking forward to staying here 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.
Aerial view

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great stay, easy location."
The price is CA $371
CA $491 total
includes taxes & fees
May 14 - May 15
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)
"Our 2nd stay at this home and it was perfection again. Well stocked with anything you could want and a true home away from home. Cannot imagine spending a week, with kids, in anything less. Already checking dates for our next trip north. "
A Pleasant Retreat- No Cleaning Fee & New Discounts
Paoli Den - Newly Remodeled!
Fridge, microwave, oven, stovetop

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (16)
"Everything we needed easy commute to city of wisconson, clean, great communication with the host and the host left a welcome basket for us that was focused towards the reason we were in town, world championship strongman competition. "
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, (7)
"We enjoyed our stay. Good location and view. Would stay here again."
The price is CA $288
CA $381 total
includes taxes & fees
May 14 - May 15
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)
"House was well-kept and comfortable, hosts were very accommodating before and throughout the stay. Highly recommend! "
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)
"Good spot, fun, clean, plenty to do, lots of space! "
The price is CA $317
CA $734 total
includes taxes & fees
May 4 - May 5
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, (87)
"We enjoyed our stay and everything was as expected and described. Will stay again. "
River Front Property
Riverfront Twin Home
Property grounds

Riverfront Twin Home

10.0 out of 10, Exceptional, (22)
"Perfect for a weekend getaway."
The price is CA $207
CA $454 total
includes taxes & fees
May 4 - May 5
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, (479)
"Serenity in the woods with a very unique stay. "
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, (10)
"We really enjoyed the stay. The house was really neat and very clean. The game room was awesome."
The price is CA $469
CA $994 total
includes taxes & fees
May 2 - May 3
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, (9)
"Place was awesome and in a great location"
The price is CA $550
CA $1,314 total
includes taxes & fees
May 5 - May 6
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, (54)
"We enjoyed the comfort and decorations added for the holidays so we could spend time near our family. The place was well appointed, clean and owners were responsive. We would book again. "
The price is CA $186
CA $302 total
includes taxes & fees
May 4 - May 5
Ohio Street Retreat-hot tub, massage chair, pool
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Miscellaneous

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

9.8 out of 10, Exceptional, (34)
"We were looking forward convenient location in Madison to see family and this place was perfect!"
The price is CA $404
CA $790 total
includes taxes & fees
May 13 - May 14
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, (41)
"Great stay"
The Dylin
Bluegreen Odyssey Dells
Water park

Bluegreen Odyssey Dells

3.5 star property
9.4 out of 10, Exceptional, (116)
"The hotel was great along with all the staff!!"
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.