Southwest Wisconsin Holiday Rentals

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Holiday Rentals in Southwest Wisconsin

Tamarack Wisconsin Dells a Ramada by Wyndham
3.0 star property
9.2 out of 10, Wonderful, 898 reviews
"Great place to stay. Very nice and clean. Staff is very friendly"
Tamarack Wisconsin Dells a Ramada by Wyndham
Caribbean Club Resort
3.0 star property
8.0 out of 10, Very good, 315 reviews
"Great resort , very clean and comfortable!"
Caribbean Club Resort
*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
9.8 out of 10, Exceptional, 115 reviews
"Cozy property with nice trail nearby. Walking distance to main street Dells."
The price is NZ$467
includes taxes & fees
19 Jun - 20 Jun
*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
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Bluegreen Vacations Odyssey Dells Resort
3.5 star property
9.2 out of 10, Wonderful, 76 reviews
"The only thing I did not like was the pull-out couch-very uncomfortable and the ice machine was loud. "
Bluegreen Vacations Odyssey Dells Resort
Bonanza Camping Resort
2.5 star property
7.4 out of 10, Good, 78 reviews
"It fit my needs perfectly! I needed a nice cute little cabin that would sleep 8 people. This one fit the bill! Not huge but it worked for us. I would stay again. You did have to bring your own bedding and towels, but no problem there. People at check in were nice and friendly. camp grounds were nice and people all seemed nice and happy. :)"
The price is NZ$313
includes taxes & fees
13 Jun - 14 Jun
Bonanza Camping Resort
condo with hot tub, full kitchen, & fireplace
8.4 out of 10, Very good, 39 reviews
"Very nice property. We had a fantastic stay."
condo with hot tub, full kitchen, & fireplace
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
9.8 out of 10, Exceptional, 30 reviews
"Overall, the property was very nice, and was the perfect size to accommodate all of us that were staying. I loved the location as it was back in the woods, quite, semi-private, and offered plenty of land to enjoy a bonfire, and recreational activities with my friends and family. The booking and check-in process was very easy and the host was extremely responsive to emails/questions. The only issues we had were ants in the upstairs bathroom and the yard had not been mowed in quite some time, but...
The price is NZ$303
includes taxes & fees
6 Jun - 7 Jun
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
The Harwood House
10.0 out of 10, Exceptional, 29 reviews
"We stayed 3 nights, and had a great time. Everything was as described in the listing. The sun porch was nice, and really loved the coffee bar. We stayed when it was very warm for this time of year and the upstairs window air conditioner was a life (sleep) saver! Don't hesitate to book this property."
The Harwood House
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, 10 reviews
"Space is clean, property is very pretty! Pool wasn’t ready for use, but can imagine it would add even more to the a summer stay! Owner is easy to communicate with. Ran into severe weather - owners were welcoming and ensured we were safe at all times. We will definitely be back to visit again!"
The price is NZ$222
includes taxes & fees
5 Jun - 6 Jun
Enjoy Nature with Full Comfort!
*Arcade Games | WildThing Lodge @ DellsVacay | Amazing 5 BR | 2400 Sq Ft Deck | Fire Pit
9.8 out of 10, Exceptional, 82 reviews
"Good"
The price is NZ$749
includes taxes & fees
12 Jun - 13 Jun
*Arcade Games | WildThing Lodge @ DellsVacay | Amazing 5 BR | 2400 Sq Ft Deck | Fire Pit
Comfortable 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
10.0 out of 10, Exceptional, 20 reviews
"The house was well prepared and very clean. Even was decorated for the holidays! Check in was smooth and easy, communication was great. We had a great time."
The price is NZ$876
includes taxes & fees
5 Jun - 6 Jun
Comfortable 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells
10.0 out of 10, Exceptional, 184 reviews
"This was such a perfect place for our large group of friends! Plenty of space, clean and so close to hiking and the outdoor bar nearby was fun."
Brand New Cabin For Getaway Vacation - 1 Mile From Devil's Lake And Close Dells
Sunset Cove 303 · Steph's Waterfront Retreat
10.0 out of 10, Exceptional, 31 reviews
"Property was exactly as advertised! Beautiful view of the water front."
The price is NZ$367
includes taxes & fees
17 Jun - 18 Jun
Sunset Cove 303 · Steph's Waterfront Retreat
Cottage on the river
9.4 out of 10, Exceptional, 31 reviews
"This was the perfect spot for a weekend getaway. It is quiet, peaceful, and has great views of the river. The home is small but the space is used efficiently and it had everything we needed. It's far enough out of town to feel "away from it all" but not far to get to the Dairy Way, we went twice! Great value, I'd definitely stay here again."
Cottage on the river
Wisconsin Dells Resort Condo w/ 2 Fireplaces
10.0 out of 10, Exceptional, 2 reviews
"My stay was great. The host was very nice and the condo was spotless. Highly recommend this condo"
Wisconsin Dells Resort Condo w/ 2 Fireplaces
Dog-friendly 4th-floor coursefront condo with balcony & washer/dryer
8.4 out of 10, Very good, 23 reviews
"It was very nice to stay with family. The only thing I would recommend to owner is to change sunken mattresses"
Dog-friendly 4th-floor coursefront condo with balcony & washer/dryer
Spacious Retreat with Private Swimming and Fishing Pond Near Wisconsin Dells
10.0 out of 10, Exceptional, 223 reviews
"We had such a good time in the Dells, and a great time at our VRBO! There was room for all of us (14) including a table that could hold us all plus a high chair. The kids loved swimming in their own private pond that had all the inflatables and rowing options you could want, and they fished every night with lots of success. Everything we required was there in good shape! Loved it!"
Spacious Retreat with Private Swimming and Fishing Pond Near Wisconsin Dells
Wild Rose Ranch Guest Cabin
9.8 out of 10, Exceptional, 148 reviews
"The property was just as listed. The host (Michelle) was wonderful and answered my initial (prior to visit) question quickly. We had no issues at all during our stay. This is a lovely property and was just perfect for me, hubby and the pooch. Close to town (restaurants, bars, hiking, national parks, the river walk), beautiful and quiet surroundings and the layout was well designed and suited our needs just perfect, everything was as comfortable as it could, and should, have been. Very Pleased!...
Wild Rose Ranch Guest Cabin
Centrally located condo with balcony, fireplace, and AC - water views
8.8 out of 10, Excellent, 3 reviews
"Very Clean and my hubby and son enjoy it not far from downtown Wisconsin Dells and resturant in walking distance"
Centrally located condo with balcony, fireplace, and AC - water views
Wisconsin Dells Wilderness Resort with Water park! Available July 29-August 4th.
Wisconsin Dells Wilderness Resort with Water park! Available July 29-August 4th.
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See all available properties in Southwest Wisconsin
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.

Other types of properties in Southwest Wisconsin you may be interested in

Mt. Olympus Water & Theme Park Resort
3.0 star property
6.2 out of 10, 1,838 reviews
"T"
The price is NZ$172
includes taxes & fees
5 Jun - 6 Jun
Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, 1,653 reviews
"The menu options in The Bar/Circ were very limited if gluten free"
The price is NZ$259
includes taxes & fees
16 Jun - 17 Jun
The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, 1,005 reviews
"Great location very close to university. Parking on site. Good breakfast. "
The price is NZ$285
includes taxes & fees
9 Jun - 10 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Southwest Wisconsin holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Southwest Wisconsin. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Southwest Wisconsin. Seeing all the best attractions is bound to make you fall in love with Southwest Wisconsin. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Southwest Wisconsin short-term rentals, that won’t be hard to do.

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