Southwest Wisconsin Holiday Rentals

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Holiday Rentals in Southwest Wisconsin

Suite in the heart of the center of spring green
9.8 out of 10, Exceptional, (93)
"Wonderful place to stay! Clean, welcoming, comfortable--the perfect place to overnight when seeing plays at American Players Theatre."
United States
Jessica L.
The price is AU$200
includes taxes & fees
26 Oct - 27 Oct
Suite in the heart of the center of spring green
A Comfy Cozy Cottage on Clowney
9.6 out of 10, Exceptional, (117)
"Comfortable, easy stay for a weekend. "
United States
Kelly
The price is AU$322
includes taxes & fees
28 Oct - 29 Oct
A Comfy Cozy Cottage on Clowney
Rustic Hideaway Sleeps 4 HOT TUB
10.0 out of 10, Exceptional, (33)
"The cabin was amazing and in such a beautiful area!! It was perfect for my family of 4. Highly recommend. "
United States
Bridget
The price is AU$673
includes taxes & fees
13 Nov - 14 Nov
Rustic Hideaway Sleeps 4 HOT TUB
The Bungaleau 1 Bedroom House In Cute Rivertown
9.8 out of 10, Exceptional, (89)
"Wonderful place. Great proximity to downtown and Perrot State Park. Clean and cozy.Hope to return. "
United States
Janet W.
The Bungaleau 1 Bedroom House In Cute Rivertown
Cabin on the Kickapoo
9.6 out of 10, Exceptional, (40)
"Perfect place to stay at while traveling. Easy check in and the porch was lovely. Lots of birds, too!"
United States
Cassie A.
The price is AU$472
includes taxes & fees
26 Oct - 27 Oct
Cabin on the Kickapoo
Tamarack Point Homestead
10.0 out of 10, Exceptional, (30)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
United States
Luke H.
The price is AU$183
includes taxes & fees
2 Nov - 3 Nov
Tamarack Point Homestead
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."
United States
Lisa K.
The price is AU$393
includes taxes & fees
3 Nov - 4 Nov
The Honey Haven
RiverFront Cottage>Private Pier>Firepit & Wildlife
10.0 out of 10, Exceptional, (38)
"We loved this quiet getaway! Simply perfect and simple. Great sunsets and rainbows! "
United States
Kevin
The price is AU$352
includes taxes & fees
26 Oct - 27 Oct
RiverFront Cottage>Private Pier>Firepit & Wildlife
Serenity Cottage at Mineral Point
10.0 out of 10, Exceptional, (98)
"What a wonderful place to stay. So much better than a hotel."
United States
Sharon L R.
The price is AU$274
includes taxes & fees
26 Oct - 27 Oct
Serenity Cottage at Mineral Point
Quiet And Beautiful!!
9.2 out of 10, Wonderful, (188)
"Great place to stay plenty of room and very quiet. "
United States
Matthew
The price is AU$516
includes taxes & fees
30 Oct - 31 Oct
Quiet And Beautiful!!
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! "
United States
Katie B.
The price is AU$417
includes taxes & fees
30 Oct - 31 Oct
MJ's Penthouse ,a piece of paradise on Monroe's historic square
Ohio Street Retreat-hot tub, massage chair, pool
10.0 out of 10, Exceptional, (65)
"We had a wonderful weekend enjoying all the parks the area has to offer. The pool and massage chair were a nice added perk to the property, especially after hiking in the parks."
United States
Kristine C.
The price is AU$324
includes taxes & fees
2 Nov - 3 Nov
Ohio Street Retreat-hot tub, massage chair, pool
Enjoy Nature with Full Comfort!
9.4 out of 10, Exceptional, (33)
"Beautiful, comfortable and convenient. Couldn’t have been more pleased with our stay. "
United States
Debra H.
The price is AU$192
includes taxes & fees
26 Oct - 27 Oct
Enjoy Nature with Full Comfort!
River Road Retreat
9.6 out of 10, Exceptional, (18)
"Relaxing trip with family- lived the cabin and the kids loved the basement"
United States
Nora M.
The price is AU$370
includes taxes & fees
28 Oct - 29 Oct
River Road Retreat
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
10.0 out of 10, Exceptional, (58)
"The perfect getaway spot that felt like arriving at a home away from home!"
United States
Ian B.
The price is AU$434
includes taxes & fees
26 Oct - 27 Oct
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Tiny House on the River
10.0 out of 10, Exceptional, (75)
"Was very very cute. Would stay again."
United States
Teressa G.
The price is AU$354
includes taxes & fees
5 Nov - 6 Nov
Tiny House on the River
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
9.8 out of 10, Exceptional, (168)
"very nice place to stay. we will stay again"
United States
Christie E.
The price is AU$467
includes taxes & fees
28 Oct - 29 Oct
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
Fall or Winter Getaway@ Northern Bay Resort!
10.0 out of 10, Exceptional, (72)
"Beautiful place. Very clean and the owners were easy to communicate with. We will be back! "
United States
Kelly
The price is AU$649
includes taxes & fees
29 Oct - 30 Oct
Fall or Winter Getaway@ Northern Bay Resort!
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."
United States
Tina J.
Kate's Place LHC 305 · Kate's Place - Newly Remodeled - Romantic
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
9.8 out of 10, Exceptional, (44)
"We had a great stay,property was quiet,clean,comfortable, well appointed hosts were welcoming and responsive. Our grandkids visited and enjoyed the retro artifacts."
United States
nancy h.
The price is AU$195
includes taxes & fees
26 Oct - 27 Oct
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
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.