Southwest Wisconsin Holiday Rentals

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Holiday Rentals in Southwest Wisconsin

The Dylin by Mint House
4.0 star property
9.2 out of 10, Wonderful, (101)
"Great stay at the Dylin"
The Dylin by Mint House
Steph's Waterfront Retreat
9.8 out of 10, Exceptional, (79)
"We enjoyed our stay"
The price is AU$334
includes taxes & fees
17 Nov - 18 Nov
Steph's Waterfront Retreat
Log Cabin at Lake Koshkonong - “The Overlook”
9.2 out of 10, Wonderful, (42)
"Nice quiet cabin. Quick response from host. Would stay there again. RTW"
The price is AU$262
includes taxes & fees
5 Nov - 6 Nov
Log Cabin at Lake Koshkonong - “The Overlook”
Sunrise Beach - LHC 611 · amily Fun - Walk to Noah's Ark!
9.8 out of 10, Exceptional, (44)
"The property was clean and great communication with owner."
The price is AU$501
includes taxes & fees
19 Oct - 20 Oct
Sunrise Beach - LHC 611 · amily Fun - Walk to Noah's Ark!
Sparrow's Nest - Stay at the lake, walk to Noah's Ark!
10.0 out of 10, Exceptional, (42)
"Everything was exactly as pictured. We were in town for a dance competition and it was so nice to be able to go back and forth and have space for my kids to spread out and relax. Our stay was amazing and we will definitely be booking again!!"
The price is AU$501
includes taxes & fees
12 Nov - 13 Nov
Sparrow's Nest - Stay at the lake, walk to Noah's Ark!
Ethel's Beachfront Retreat
10.0 out of 10, Exceptional, (38)
"Great place to stay. It had everything you would need."
The price is AU$314
includes taxes & fees
12 Nov - 13 Nov
Ethel's Beachfront Retreat
Piers & Pines at Island Pointe
10.0 out of 10, Exceptional, (24)
"Wonderful stay. Perfect little cabin and hosts were very helpful."
The price is AU$331
includes taxes & fees
17 Nov - 18 Nov
Piers & Pines at Island Pointe
Country home with flowing river
9.0 out of 10, Wonderful, (155)
"Everything was excellent! Extremely clean. We were in town to visit family and it was perfect for our needs. Nice little bench next to the river."
The price is AU$261
includes taxes & fees
20 Oct - 21 Oct
Country home with flowing river
Cozy 3-bedroom cabin - sleeps 10- HOT TUB- river view
2.0 star property
8.2 out of 10, Very good, (12)
"Great Cabin with a view of the Mighty Mississippi. Quiet and secluded enough but within driving distance of Viroqua"
The price is AU$410
includes taxes & fees
2 Nov - 3 Nov
Cozy 3-bedroom cabin - sleeps 10- HOT TUB- river view
Lakefront Luxury 212 · Lakefront Luxury for Families or Couples
10.0 out of 10, Exceptional, (64)
"Chris' place was great and he was a very accommodating host. I'd gladly stay here again."
The price is AU$510
includes taxes & fees
2 Nov - 3 Nov
Lakefront Luxury 212 · Lakefront Luxury for Families or Couples
WI Dells Hideaway Condo on Lake Delton - Lake access with boat slip (upon request)
9.8 out of 10, Exceptional, (33)
"This condo's location is wonderful! We could walk to Noah's Ark. We purchased Noah's Ark tickets from the home owners which let us in on multiple days---a huge plus for our grandkids and ourselves. The kitchen was well appointed. There was a large TV in each bedroom and the living room. We used the outdoor and indoor swimming pools which were great. We didn't have time to use the beach but we walked down there and it looked really nice. Would stay again!"
WI Dells Hideaway Condo on Lake Delton - Lake access with boat slip (upon request)
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
10.0 out of 10, Exceptional, (57)
"The perfect getaway spot that felt like arriving at a home away from home!"
The price is AU$436
includes taxes & fees
16 Nov - 17 Nov
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Brown Family Condo - Top Floor Views - Boat Slip
9.8 out of 10, Exceptional, (64)
"We enjoyed our stay here - everything was as described, clean, and well maintained. The hot tub was great after our days of skiing, and larger than those in most hotels."
The price is AU$484
includes taxes & fees
17 Nov - 18 Nov
Brown Family Condo - Top Floor Views - Boat Slip
The Dockview on Lake Delton - Lakefront, PIckleball, Pools
10.0 out of 10, Exceptional, (139)
"Excellent accommodations right on the lake!"
The price is AU$471
includes taxes & fees
27 Oct - 28 Oct
The Dockview on Lake Delton - Lakefront, PIckleball, Pools
Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic
10.0 out of 10, Exceptional, (64)
"Totally enjoyed our stay. This place was very nice. Felt very homey, very well kept and clean. Would definitely stay here again."
The price is AU$308
includes taxes & fees
2 Nov - 3 Nov
Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic
MJ's Penthouse ,a piece of paradise on Monroe's historic square
10.0 out of 10, Exceptional, (98)
"My husband and I stayed here and were so happy we did this home was beautiful and really something special. I highly recommend the stay here! "
The price is AU$421
includes taxes & fees
19 Oct - 20 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
The Bungaleau 1 Bedroom House In Cute Rivertown
9.8 out of 10, Exceptional, (88)
"Wonderful place. Great proximity to downtown and Perrot State Park. Clean and cozy.Hope to return. "
The Bungaleau 1 Bedroom House In Cute Rivertown
The Honey Haven
10.0 out of 10, Exceptional, (45)
"This VRBO was a wonderfully clean and comfortable retreat in the driftless. The owners (and their dog) were very friendly, and the location was beautiful."
The price is AU$393
includes taxes & fees
18 Oct - 19 Oct
The Honey Haven
Grace-Jo Vacation Home at Tamarack
10.0 out of 10, Exceptional, (73)
"Close to concert venue and Dell’s facilities. Enjoyed our stay in all respects."
The price is AU$566
includes taxes & fees
3 Nov - 4 Nov
Grace-Jo Vacation Home at Tamarack
Tamarack Point Homestead
10.0 out of 10, Exceptional, (30)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
The price is AU$183
includes taxes & fees
19 Oct - 20 Oct
Tamarack Point Homestead
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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Top Southwest Wisconsin Hotel Reviews

Find out more about Southwest Wisconsin

Everything you need to know about Southwest Wisconsin holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Wisconsin holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwest Wisconsin holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southwest Wisconsin holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwest Wisconsin. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwest Wisconsin holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwest Wisconsin holiday rentals we have selected for you start as low as AU$266 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southwest Wisconsin rentals

At Expedia, we put the best Southwest Wisconsin holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwest Wisconsin rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwest Wisconsin holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwest Wisconsin. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.