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

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, (964)
"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.
Exterior

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 AU$573
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
Exterior

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 AU$1,553
includes taxes & fees
1 Sept - 2 Sept
Red Oak Lodge @ Spring Brook Resort
Cozy Boutique Motel on the Lake Delton Strip
Outdoor pool

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 AU$189
includes taxes & fees
12 Aug - 13 Aug
Cozy Boutique Motel on the Lake Delton Strip
Stunning, serene, rustic house in the woods near Spring Green, Wisconsin
TV, DVD player, books, video library

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

10.0 out of 10, Exceptional, (475)
"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
Exterior detail

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 AU$738
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
Interior

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

9.8 out of 10, Exceptional, (12)
"Home is located in a great area with all the amenities needed. Very nice home!"
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse
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, (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)
Terrace/patio

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
Exterior

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 AU$355
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
Terrace/patio

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
Smart TV, DVD player, books

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
Smart TV, fireplace, video games, DVD player

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
Exterior

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 AU$288
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
Exterior

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
Exterior

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!
Outdoor dining

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
Interior

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 AU$716
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)
Property grounds

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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