Southwest Wisconsin Holiday Rentals

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Holiday Rentals in Southwest Wisconsin

Indoor pool, seasonal outdoor pool
Tamarack Wisconsin Dells a Ramada by Wyndham
3.0 star property
9.2 out of 10, Wonderful, (895)
"It was amazing just like being at home quiet east to find very well kept up"
Tamarack Wisconsin Dells a Ramada by Wyndham
Exterior
Caribbean Club Resort
3.0 star property
8.0 out of 10, Very good, (313)
"Very home away from home. Condo unit was clean and had our most desired amenities fireplace and jacuzzi tub "
Caribbean Club Resort
Property grounds
*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
9.8 out of 10, Exceptional, (113)
"Absolutely perfect for 2 couple that want to get away for a few days. The views of the water are beautiful and just a short walk to downtown. Great communication with host Ashley. Already trying to find a date to come back in the fall."
The price is NZ$472
includes taxes & fees
27 May - 28 May
*Pool/Hot Tub | Riverwalk Retreat @ Dells Vacay | Cozy 2 BR Condo
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Water park
Bluegreen Vacations Odyssey Dells Resort
3.5 star property
9.2 out of 10, Wonderful, (76)
"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
Seasonal outdoor pool
Bonanza Camping Resort
2.5 star property
7.4 out of 10, Good, (78)
"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$320
includes taxes & fees
6 Jun - 7 Jun
Bonanza Camping Resort
Fridge, microwave, oven, stovetop
The Harwood House
10.0 out of 10, Exceptional, (28)
"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
Exterior
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
9.8 out of 10, Exceptional, (30)
"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$259
includes taxes & fees
28 May - 29 May
Nine mins from Down Town Wisconsin Dells. Pet Friendly, Private Area
condo with hot tub, full kitchen, & fireplace
8.4 out of 10, Very good, (38)
"Very nice property. We had a fantastic stay."
condo with hot tub, full kitchen, & fireplace
Indoor pool, a heated pool
Sunset Cove 303 · Steph's Waterfront Retreat
10.0 out of 10, Exceptional, (30)
"Property was exactly as advertised! Beautiful view of the water front."
The price is NZ$403
includes taxes & fees
17 Jun - 18 Jun
Sunset Cove 303 · Steph's Waterfront Retreat
Exterior
*Arcade Games | WildThing Lodge @ DellsVacay | Amazing 5 BR | 2400 Sq Ft Deck | Fire Pit
9.8 out of 10, Exceptional, (82)
"Good"
The price is NZ$757
includes taxes & fees
30 May - 31 May
*Arcade Games | WildThing Lodge @ DellsVacay | Amazing 5 BR | 2400 Sq Ft Deck | Fire Pit
On the beach
Madison & ~UW~-Madison Area Lakefront Home
9.8 out of 10, Exceptional, (165)
"The cottage is clean and well stocked for a long weekend. The view of the lake is beautiful, and I'm sure it's even better in the warm months. We had everything we needed. Great little house for a long weekend."
Madison & ~UW~-Madison Area Lakefront Home
Fridge, microwave, oven, stovetop
Tall Pines Lodge- Cottages On Serenity Lake- Sitting on 80 Acres Of Wildlife!
9.8 out of 10, Exceptional, (62)
"We had a family graduation out in Wisconsin and I needed a place to fit our kids and grandkids! Was so happy to find this cute place on the lake with plenty of room for everyone to sleep! Everyone enjoyed the space, using the hot tub and the beautiful view! I liked that no one else could get into the property as it was gated. We so wish we could have stayed longer! Our host were amazing and Brian was reachable by text if we had any questions! Would love to come stay longer in the future!"
Tall Pines Lodge- Cottages On Serenity Lake- Sitting on 80 Acres Of Wildlife!
Property grounds
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"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$210
includes taxes & fees
27 May - 28 May
Enjoy Nature with Full Comfort!
Outdoor dining
Comfortable 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
10.0 out of 10, Exceptional, (20)
"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$849
includes taxes & fees
27 May - 28 May
Comfortable 4-Bedroom Home 1 Block from Downtown Wisconsin Dells
Terrace/patio
Centrally located condo with balcony, fireplace, and AC - water views
8.8 out of 10, Excellent, (3)
"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
Exterior
Spacious Retreat with Private Swimming and Fishing Pond Near Wisconsin Dells
10.0 out of 10, Exceptional, (222)
"Everything was great , anything you can possible Need for a trip he had provided and that was great"
Spacious Retreat with Private Swimming and Fishing Pond Near Wisconsin Dells
Property grounds
Private Amish Log Cabin Getaway
9.6 out of 10, Exceptional, (107)
"Beautiful little cabin, very solid with heated floors! It was so quiet, and the comfy beds provided great sleep. We watched movies on the big tv and curled up for reading on the sofas. Kitchen had all the cooking utensils and dishes, so it was easy to prepare meals. Perfect place to get away from it all to relax, rewind, and renew."
Private Amish Log Cabin Getaway
Property grounds
Lake home with jetted tub & washer/dryer - steps from beach & restaurants
9.0 out of 10, Wonderful, (14)
"The bunk beds are too noisy"
Lake home with jetted tub & washer/dryer - steps from beach & restaurants
Fridge, microwave, oven, stovetop
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
Aerial view
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

Exterior
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1629)
"I would recommend staying at this hotel. Very clean and updated. "
The price is NZ$262
includes taxes & fees
27 May - 28 May
The Madison Concourse Hotel and Governor's Club
Water park
Mt. Olympus Water & Theme Park Resort
3.0 star property
6.2 out of 10, (1850)
"Great"
The price is NZ$174
includes taxes & fees
27 May - 28 May
Mt. Olympus Water & Theme Park Resort
Exterior
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1004)
"Good location"
The price is NZ$283
includes taxes & fees
27 May - 28 May
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.

Recent reviews of Southwest Wisconsin properties
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