Holiday Rentals in Southwest Wisconsin

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Holiday Rentals in Southwest Wisconsin

Bluegreen Vacations Odyssey Dells Resort

3.5 star property
9.2 out of 10, Wonderful, (89)
"Staff was very helpful and friendly. Room was in excellent condition."
Bluegreen Vacations Odyssey Dells Resort

Caribbean Club Resort

3.0 star property
8.0 out of 10, Very good, (331)
"The condo was very nice and location was very good by the pool "
Caribbean Club Resort

*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat

9.8 out of 10, Exceptional, (135)
"Condo on ground level so a few steps down. Clean and pleasant. Location along river very good. Next to public boat ramp so watched boats come and go. Woderful host!!!! Very quick response and pleasant."
The price is €285
includes taxes & fees
26 Nov - 27 Nov
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat

Bayfront Cottage is a 3 bedroom house on Richmond Bay.

8.4 out of 10, Very good, (26)
"We were up in the are for Oktoberfest Race Weekend at Lacrosse Fairgrounds Speedway. Property had everything you needed, as we were not there a ton. Just sleeping and showers. Would be a great place during the summer, with a riverfront back yard, and plenty of space to hang out and have a fire, etc."
Bayfront Cottage is a 3 bedroom house on Richmond Bay.

Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells

9.8 out of 10, Exceptional, (198)
"The place was beautiful and was set up great for our group. Had an amazing time! Thank you."
Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (940)
"Pleasant stay and affordable "
Tamarack Wisconsin Dells a Ramada by Wyndham

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

9.8 out of 10, Exceptional, (29)
"The best thing about this house is its proximity to Madison in general and to the river. I loved taking a kayak out on the river around sunrise. Really beautiful. It's close to many fun activities in Madison too. The house itself is comfortable. Hosts are responsive and helpful. Kitchen is lovely. One helpful tip is that this house is on a busy street. There is some traffic noise at night. Not a huge deal but I wish I had known ahead of time and prepared for it. Overall a good place with...
The price is €517
includes taxes & fees
1 Dec - 2 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Steph's Waterfront Retreat

10.0 out of 10, Exceptional, (48)
"Great lacotion,just thecright size"
The price is €192
includes taxes & fees
2 Dec - 3 Dec
Steph's Waterfront Retreat

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (117)
"We were here for the PSU- Wisconsin game and the house worked great. Maybe just a new shower curtain liner in the upstairs bathroom 😁"
Conveniently Located just off University Avenue on Madison's West Side

Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

9.0 out of 10, Wonderful, (73)
"You’ll love it here. Close to many attractions. "
Lakeside Haven Home On Birch Lake, Sleeps Up To 12 People.

Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

10.0 out of 10, Exceptional, (235)
"We first stayed here for our wedding in fall 2023 and loved it. We stayed again for our first anniversary. It’s a great little place, on a great little piece of property! "
Beautiful new contemporary home, quiet wooded lot minutes from Devils Lake

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (98)
"Beautiful space, very relaxing. We had a great stay!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Adventure Trails

10.0 out of 10, Exceptional, (28)
"Great place for my husband and I to stay on a short anniversary getaway."
The price is €128
includes taxes & fees
16 Dec - 17 Dec
Adventure Trails

🏞New Log Cabin*Perfect Location by Devil's Lake*Close to Dells*Ski*Fireplace*🏕

10.0 out of 10, Exceptional, (83)
"This beautiful home was spotlessly clean, lovely in its design and decor. All the furnishings were top notch and comfortable, from chairs/couches to beds. It is tucked into a quiet setting with nice views, yet is close to local offerings. We enjoyed our stay and will definitely come back. "
🏞New Log Cabin*Perfect Location by Devil's Lake*Close to Dells*Ski*Fireplace*🏕

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (215)
"This house was perfect for me and my adult son and daughter. We all had or own bed, the house was clean and comfortable and we absolutely loved the style of the older homes in the neighborhood. Every you could want was close by and the host was amazing. "
A Pleasant Retreat- No Cleaning Fee & New Discounts

Josie's On The Bay - Waterfront, Fireplace, Roku

9.6 out of 10, Exceptional, (46)
"Fun girls’ weekend! Great property and location "
The price is €297
includes taxes & fees
9 Dec - 10 Dec
Josie's On The Bay - Waterfront, Fireplace, Roku

Champagne Chalet @ Spring Brook Resort

9.8 out of 10, Exceptional, (46)
"This is a beautiful home in a great location. We had everything we needed for our family of nine to be comfortable. The location was perfect and enabled us to reach local attractions in a minimum amount of time. "
The price is €970
includes taxes & fees
26 Nov - 27 Nov
Champagne Chalet @ Spring Brook Resort

Enjoy this newly remodeled house located on Lake Onalaska.

10.0 out of 10, Exceptional, (109)
"Quiet, cozy, clean, easy to locate and in centet of all towns, trails and parks."
Enjoy this newly remodeled house located on Lake Onalaska.

Condo with full kitchen, & fireplace

8.4 out of 10, Very good, (45)
"Very nice property. We had a fantastic stay."
Condo with full kitchen, & fireplace

Lovely condo with on-site water park, balcony, kitchenette & central AC

8.0 out of 10, Very good, (6)
"The bee hive on the balcony "
Lovely condo with on-site water park, balcony, kitchenette & central AC
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 types of properties in Southwest Wisconsin you may be interested in

The Madison Concourse Hotel and Governor's Club

3.5 star property
9.4 out of 10, Exceptional, (2109)
"This was a great place to stay for the Oregon/Wisconsin game. The staff were super friendly. The airport shuttle was very convenient. And the location of this hotel was perfect! Within walking distance to so much. Highly recommend! "
The price is €123
includes taxes & fees
1 Dec - 2 Dec
The Madison Concourse Hotel and Governor's Club

Mt. Olympus Water & Theme Park Resort

3.0 star property
6.6 out of 10, (1946)
"Very economical. Some trade offs but worth it."
The price is €71
includes taxes & fees
2 Dec - 3 Dec
Mt. Olympus Water & Theme Park Resort

Best Western Plus InnTowner Madison

3.0 star property
9.0 out of 10, Wonderful, (1027)
"Great buffet breakfast and free happy hour hotdogs and beers before the Wisconsin Oregon game. Remodeled guest rooms with new tile shower. Very friendly and helpful staff. "
The price is €120
includes taxes & fees
8 Dec - 9 Dec
Best Western Plus InnTowner Madison
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.