Holiday Homes in Southwest Wisconsin

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Southwest Wisconsin and around

Tamarack Wisconsin Dells a Ramada by Wyndham
Relax by the pool surrounded by lush greenery and a shaded play area.

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (965)
"Was in great shape "
Tamarack Wisconsin Dells a Ramada by Wyndham
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Saddleback building features a brick facade and multiple windows on each floor.

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

9.6 out of 10, Exceptional, (27)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is €324
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Red Oak Lodge @ Spring Brook Resort
Escape to a serene log cabin retreat with a spacious deck and large windows.

Red Oak Lodge @ Spring Brook Resort

9.6 out of 10, Exceptional, (44)
"This was a great place for a family holiday weekend. All 12 people had a great time and we left with many happy memories."
The price is €878
includes taxes & fees
27 Aug - 28 Aug
Red Oak Lodge @ Spring Brook Resort
Cozy Boutique Motel on the Lake Delton Strip
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

Cozy Boutique Motel on the Lake Delton Strip

9.0 out of 10, Wonderful, (24)
"Accurate to listing and nice affordable place to stay at!"
The price is €105
includes taxes & fees
25 Aug - 26 Aug
Cozy Boutique Motel on the Lake Delton Strip
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
Relax in this serene living area with a high ceiling, large window, and lush views of the surrounding greenery.

Stunning, serene, rustic house in the woods near Spring Green, Wisconsin

10.0 out of 10, Exceptional, (476)
"We wanted to visit the Frank Lloyd Wright sites. Perfect location for all of them!"
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
THE WASHINGTON HOUSE - A 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
Welcome to The Washington House, a charming vacation rental in Wisconsin, surrounded by beautiful gardens.

THE WASHINGTON HOUSE - A 4-Bedroom Home 1 Block from Downtown Wisconsin Dells

10.0 out of 10, Exceptional, (39)
"The home is well kept and charming. It had everything we needed. Easy to book and the host communicated great. "
The price is €418
includes taxes & fees
2 Sept - 3 Sept
THE WASHINGTON HOUSE - A 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
3-Bedroom House Steps From Town and Waterfront!
Outdoor dining

3-Bedroom House Steps From Town and Waterfront!

3-Bedroom House Steps From Town and Waterfront!
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse
Relax in a serene setting with expansive forest views from large windows, accompanied by a comfortable seating area with two armchairs and a small table.

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

9.8 out of 10, Exceptional, (12)
"Great stay. Clean and comfortable. Would stay again."
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
Relax in a serene hot tub surrounded by lush greenery and a seating area.

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

10.0 out of 10, Exceptional, (167)
"Hands down the BEST property we have ever stayed in! It is a beautiful home with so many personal touches (chocolates, wine, local gift certificate) and superbly stocked kitchen and bathrooms. Host was very quick with responses. Would love to come back!"
Gorgeous Log Home featuring 8-person outdoor HOT TUB-available year round.
Lake Arrowhead lakefront (4 bedroom and Game Room)
Enjoy a peaceful evening by the fire pit surrounded by a well-manicured lawn and comfortable seating.

Lake Arrowhead lakefront (4 bedroom and Game Room)

10.0 out of 10, Exceptional, (33)
"The property is a great location with tons of amenities to help enjoy all there is to offer. Hosts were responsive and helpful."
Lake Arrowhead lakefront (4 bedroom and Game Room)
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Stunning Victorian-style building with a charming front porch and beautifully manicured lawn.

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (32)
"House was amazing and was exactly as advertised. Would definitely stay again."
The price is €200
includes taxes & fees
13 Aug - 14 Aug
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion
Beach Lake Retreat with Private Lake and Hot Tub
Relax in the outdoor hot tub overlooking the serene water.

Beach Lake Retreat with Private Lake and Hot Tub

10.0 out of 10, Exceptional, (33)
"Had an amazing time at this beautiful house."
Beach Lake Retreat with Private Lake and Hot Tub
Elegant country retreat near Spring Green w expansive views of Driftless Region
Relax in a warm and inviting space with a high ceiling and comfortable seating area.

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

10.0 out of 10, Exceptional, (52)
"The four of us enjoyed staying at this home. We were really wowed by the beauty of the home, and the property was private and spacious. We had fun walking around enjoying nature. "
Elegant country retreat near Spring Green w expansive views of Driftless Region
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Relax in this serene room with a high ceiling, ceiling fan, and large window offering a view of the backyard and deck.

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

9.6 out of 10, Exceptional, (61)
"The property was beautiful and our group of 8 had tons of space. It was beautiful and we wish we could’ve stayed longer. We would definitely stay there again. "
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Two-story house with a garage on the ground floor, surrounded by a well-maintained lawn and stone wall.

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

10.0 out of 10, Exceptional, (14)
"I had the pleasure of spending a short weekend at The Earthhouse BnB in Mt. Horeb, and it was absolutely wonderful! The property is tucked away in a serene, peaceful location that provided the perfect escape from the hustle and bustle of everyday life. The BnB itself is charming and cozy, with unique touches that made it feel like a true home away from home."
The price is €163
includes taxes & fees
24 Aug - 25 Aug
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
ONE OF A KIND vacation rental with a view
Stylish building surrounded by lush greenery, featuring a glass facade and brick architecture.

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Stunning home with a front porch and a charming entrance.

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (144)
"Enjoyed our stay. House worked out great- the number of beds/bedrooms and having 2 bathrooms was wonderful. Close to the downtown- easy 30 minute walk."
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Spacious New Lisbon Home w/ Lake Access!
Enjoy expansive views of the surrounding landscape from the deck's comfortable seating areas.

Spacious New Lisbon Home w/ Lake Access!

10.0 out of 10, Exceptional, (24)
"This place was amazing, we’ll definitely be back in the summer to enjoy the lake and the additional amenities!"
Spacious New Lisbon Home w/ Lake Access!
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Enjoy cooking in this kitchen with a large island and windows offering a view of the outdoors.

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (7)
"We loved everything about this property. Would definitely stay there again."
The price is €406
includes taxes & fees
1 Sept - 2 Sept
Two Bedroom with views of Lake Monona in the heart of downtown Madison
5 Bedroom Wooded Paradise (mins from wi dells)
Surrounded by dense foliage, a campfire crackles in a secluded setting.

5 Bedroom Wooded Paradise (mins from wi dells)

9.4 out of 10, Exceptional, (3)
"We were a group of 10 and had plenty of room"
5 Bedroom Wooded Paradise (mins from wi dells)
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

Baymont Inn & Suites by Wyndham Madison

Baymont Inn & Suites by Wyndham Madison

10/10 Excellent
"All was good"
David 1-night trip
Posted 1 day ago
Baymont Inn & Suites by Wyndham Madison