Southwest Wisconsin Holiday Rentals

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Holiday Rentals in Southwest Wisconsin

Bluegreen Vacations Odyssey Dells Resort

3.5 star property
9.2 out of 10, Wonderful, (96)
"Large rooms and everything you need!"
Bluegreen Vacations Odyssey Dells Resort

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (946)
"Great"
Tamarack Wisconsin Dells a Ramada by Wyndham

The Dylin by Locale

4.0 star property
9.8 out of 10, Exceptional, (7)
"This is a fabulous location. The building is beautiful. The beds are cozy and the units have all the amenities one would need. Absolutely fabulous! The only complaint is communication is lacking In the weekends if booking or having issues. M-Friday the text communication is great. I’m having an issue with my unit. And they are telling they are fully booked. Yet I’m physically here and only a few people are in the third floor! I’m staying here long term so I don’t appreciate the mis...
The price is AU$151
includes taxes & fees
17 Feb - 18 Feb
The Dylin by Locale

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

10.0 out of 10, Exceptional, (31)
"We had a fantastic time relaxing around the house and enjoying strolls through the prairie to the tea house to watch sunsets. This is a repeat visit for us and never disappoints. Thanks again."
Elegant country retreat near Spring Green w expansive views of Driftless Region

Tiny House on the River

10.0 out of 10, Exceptional, (55)
"We had an awesome time! Perfect little weekend getaway that we needed! My girlfriend and I were very impressed with the home and how it was equipped for our stay! Definitely recommend, these folks are great people! "
The price is AU$343
includes taxes & fees
17 Feb - 18 Feb
Tiny House on the River

Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

2.0 star property
10.0 out of 10, Exceptional, (5)
"The place was clean, and my family had a wonderful time during our stay."
The price is AU$1,328
includes taxes & fees
17 Feb - 18 Feb
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (224)
"Our recent stay in Sun Prairie was wonderful. Randy and Connie are outstanding hosts. They greeted us when we arrived. Showed us all the features of the home and were available to answer any questions. They suggested places to take our grandchildren. The house was conveniently located to everything we wanted to do in Sun Prairie and is a short drive to Madison. Our grand daughter told us she wants to come back and stay in this our again."
The price is AU$458
includes taxes & fees
17 Feb - 18 Feb
A Pleasant Retreat- No Cleaning Fee & New Discounts

Field House | Game Room | DOWNTOWN Dells | Basketball Court| Arcade

9.8 out of 10, Exceptional, (126)
"The detached garage is a game changer!"
The price is AU$758
includes taxes & fees
17 Feb - 18 Feb
Field House | Game Room | DOWNTOWN Dells | Basketball Court| Arcade

All Inclusive Getaway ( The Pool House )

10.0 out of 10, Exceptional, (52)
"We have stayed at the Pool House in January for the last 4 years. Our kids and our grandkids enjoy staying there more and more each year. The pool continues to be a great gathering area for our family. Chad has always responded to questions quickly and professionally. "
All Inclusive Getaway ( The Pool House )

New Listing!Beautiful Log Cabin near Devil`s Lake.

9.8 out of 10, Exceptional, (301)
"We couldn’t have asked for a better house for our family vacation. We traveled from Arkansas and Indiana to spend a week together in the Wisconsin Dells area. The house had plenty of space and amenities to keep us all happy when we were at “home”. The pool table and ping pong table were a huge hit! The house was well stocked and our host was quick to respond anytime we reached out. We would definitely stay here again!"
New Listing!Beautiful Log Cabin near Devil`s Lake.

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

9.6 out of 10, Exceptional, (51)
"Everything was great, and we had a wonderful stay! The property was clean, well-maintained, and cozy. We enjoyed visiting the pool area, and liked being close to downtown! Thanks!"
The price is AU$488
includes taxes & fees
18 Feb - 19 Feb
Josie's On The Bay - Waterfront, Fireplace, Roku

Caribbean Club Resort

3.0 star property
8.0 out of 10, Very good, (334)
"Very friendly staff! Great location. Place was clean. Perfect for family with children. I would definitely come back in the near future!!! "
Caribbean Club Resort

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

9.8 out of 10, Exceptional, (29)
"Amber is an excellent host. House was very clean, and easy check in and check out. Would highly recommend."
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

River Front Property

10.0 out of 10, Exceptional, (85)
"We loved staying at this rental! It was very clean and cozy and had a great view of the river. Close to downtown LaCrosse but just far enough from the noise and foot traffic. Ben was kind and accommodating and always quickly responded to any questions we had. Would highly recommend! "
River Front Property

The Sunset Condo at Sunset Cove

3.0 star property
10.0 out of 10, Exceptional, (13)
"Right on the river and away from the main strip at the Dells but close enough to walk to many activities. "
The price is AU$541
includes taxes & fees
17 Feb - 18 Feb
The Sunset Condo at Sunset Cove

Steph's Waterfront Retreat

9.8 out of 10, Exceptional, (56)
"Relaxing, quiet easy to deal with "
The price is AU$343
includes taxes & fees
17 Feb - 18 Feb
Steph's Waterfront Retreat

Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells

9.8 out of 10, Exceptional, (104)
"Stayed the weekend to ski at Cascade Mountain. House was clean, comfortable, well-appointed. We had plenty of room for 3 families with little kids. Ashley was extremely responsive and even mailed me something I had left behind. Definitely recommend!"
The price is AU$768
includes taxes & fees
17 Feb - 18 Feb
Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells

Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!

10.0 out of 10, Exceptional, (52)
"This was a great place for our large family gathering. Plenty of space for sleeping, eating and fun times with large game room downstairs. Something for everyone. Well furnished and management was great to work with. Highly recommend."
Lakefront! Huge Game RM + Chefs Kitchen! Sleep 40!

Spacious 5-bedroom 4- bath house 1- mile to Devil's Lake.

Spacious 5-bedroom 4- bath house 1- mile to Devil's Lake.

Lavish House w/ Patio - 2 Blocks to Green Lake!

9.8 out of 10, Exceptional, (65)
"Friends gathered and all 4 of us enjoyed our time at this rental for a weekend. Clean, spacious, comfortable. There was only one slight down side, all conversation and the one movie we watched that weekend were disrupted by the sound of the furnace running. Had it not been cold outside, perhaps we wouldn't have noticed. We adapted and smiled whenever the heat would turn on. All else was a pleasure. "
Lavish House w/ Patio - 2 Blocks to Green Lake!
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, (2312)
"The hotel was very quiet. I’ve been running into a lot of hotels that have dogs barking through the night or smell like urine. This hotel was exceptional the bed, the pillows, the shower. The shower was exhilarating. The pressure was firm. The water temperature was very hot just like I like it Back to the bed. The bed was like a cloud. I really loved it. My stay was short I would definitely return just to stay at the hotel."
The price is AU$262
includes taxes & fees
23 Feb - 24 Feb
The Madison Concourse Hotel and Governor's Club

Best Western Plus InnTowner Madison

3.0 star property
9.2 out of 10, Wonderful, (1005)
"The rooms are spacious and comfortable, the restaurant offers delicious food, and the location is convenient and well-maintained."
The price is AU$229
includes taxes & fees
23 Feb - 24 Feb
Best Western Plus InnTowner Madison

Great Wolf Lodge Wisconsin Dells

3.5 star property
8.4 out of 10, Very good, (1005)
"Nice!!!"
The price is AU$325
includes taxes & fees
17 Feb - 18 Feb
Great Wolf Lodge Wisconsin 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.