Southwest Wisconsin Holiday Rentals from NZ$248: Search Short-Term Rentals

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Our top choices for Southwest Wisconsin holiday rentals

A wooden cabin with a porch, two windows, and a star decoration on the wall.

1. River Road Retreat

Muscoda

Robert S.

includes taxes & fees

28 Sept - 29 Sept

A cabin with a dining area, a bicycle, and a sign reading "Vangelis".

2. Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

Wild Rose

Jennifer

includes taxes & fees

13 Oct - 14 Oct

A single-story house with a gabled roof, a front porch, and a small front yard with mulch and plants.

3. Colorful getaway in friendly Driftless village

Wonewoc

Emily B.

includes taxes & fees

28 Sept - 29 Sept

A living room with a television, a coffee table, a sofa, and a dining area in the background.

4. Hillsboro Driftless Guesthouse is cozy and ready for you!

Hillsboro

Dan G.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck leading to a white door with a sign reading "SIENNA SUNSET CHASER A PETITE RETREAT."

5. Yukon Trails RV & Camping Resort

Lyndon Station

Alessandra

includes taxes & fees

28 Sept - 29 Sept

Two white hammocks hanging on a wooden porch with a view of a garden.

6. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

Lyndon Station

Eukesha

includes taxes & fees

28 Sept - 29 Sept

A cabin with a wooden interior, a fireplace, a sofa, a kitchen area, and large windows.

7. Your adventure begins the second you arrive!

Norwalk

Betsy D.

includes taxes & fees

6 Oct - 7 Oct

A cozy room with a wooden floor, a blue sofa, a door with windows, and a lamp on a table.

8. A Comfy Cozy Cottage on Clowney

Mineral Point

Tashia N.

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin surrounded by snow-covered trees.

9. Cabin on the Kickapoo

Readstown

Joel M.

includes taxes & fees

5 Oct - 6 Oct

10. Serenity Cottage at Mineral Point

Mineral Point

Katie K.

includes taxes & fees

28 Sept - 29 Sept

A rural landscape with a wooden fence, a field of crops, and distant buildings including a silo and a house.

11. Peaceful Country Comfort W Panoramic Views of Big Creek Valley

Sparta

Todd B.

includes taxes & fees

28 Sept - 29 Sept

A log cabin with a large porch, multiple windows, and a stone pathway leading to the entrance.

12. Rustic Hideaway Sleeps 4 HOT TUB

De Soto

Susan

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

13. Ohio Street Retreat-hot tub, pool, massage chair

Prairie du Chien

nate k.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with a bench, a white door, and hanging flower baskets.

14. The Bungaleau 1 Bedroom House In Cute Rivertown

Downtown Trempealeau

Lisa C.

includes taxes & fees

29 Sept - 30 Sept

A compact kitchen with a built-in stove, a microwave, and a large TV.

15. Arrowhead Resort Campground

Wisconsin Dells

Alexis

includes taxes & fees

28 Sept - 29 Sept

A dining area with a wooden table and chairs, a window with a view of trees, and a wall-mounted artwork of a chef.

16. Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

Lyndon Station

Arthur A.

includes taxes & fees

28 Sept - 29 Sept

A lakeside view with beach chairs and a dock.

17. The Docksider - Couples & Young Families - Lakefront!

Lake Delton

Tom T.

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bunk bed, a single bed, a ceiling fan, and a window with blinds.

18. Peyton's Place at Tamarack - Great Location!

Wisconsin Dells

Joyce W.

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin with a porch, a picnic table, and a mailbox.

19. Quiet And Beautiful!!

Warrens

Matthew

includes taxes & fees

28 Sept - 29 Sept

A cozy log cabin interior with a fireplace, a sofa, and a large window offering a view of the outdoors.

20. Tiny House on the River

Black River Falls

Taylor V.

includes taxes & fees

28 Sept - 29 Sept

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Top Southwest Wisconsin Hotel Reviews

Dellshire Resort

10/10 Excellent

"Our family loved our stay here and it was nice having everything under one roof."

The Wisconsin Hotel & Conference Center

10/10 Excellent

"This was a great stay in Wisconsin Dells! Perfect for a couples, family, or solo trip. The restaurant has SUCH good food! SILO bar and rooftop were great. The pool and hot tub could have been warmer but it was still great to use. Sauna was such a plus! The rooms were comfortable and very roomy. Not much storage but two sinks, which was convenient for more than one guest. Can’t wait to stay again!"

Natura Vue Resort & Boathouse

10/10 Excellent

"We opted for the lake view and were glad we did. It was beautiful. All of the staff we interacted with was helpful and cheerful. We did not use the restaurant this time but have eaten there before and have been happy with it. The only downside was that we were required to wear a wristband the entire time even though we would not be using the pool area. The wristband is used in place of a key card for the room door. Neither one of us cared for that at all. It was uncomfortable to sleep in even though we kept it as loose as possible."

Natura Aloha Reach Resort

10/10 Excellent

"We visited the Dells and ate at the restaurant overlooking the lake and saw the kids in the water. I decided on our next trip we would stay here. It was after Labor Day so the lake did not have the inflatables, so that was sad. We will have to come back next summer. The pool was open outside. And that was an added bonus because most hotel pools were closed in mid-September. I liked the access to the lake even though we did not go in the lake. We just sat by the beach. There is a fire pit for use and you can buy wood. I will do that next time. The view from the hotel of the lake was fun. Next time I would rather stay in a tiki room. The price isn’t more. The hotel was clean. You can tell it is an older hotel and some places were worn, but honestly that is sort of the charm. It was build before the big resorts was a thing. For the price it was a good place to stay. I would return."

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 favorite 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 depends 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 NZ$248 per night. Entering your travel dates in the search wizard you might find 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.

Southwest Wisconsin Holiday Rentals

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Check prices for these dates

Our top choices for Southwest Wisconsin holiday rentals

1. River Road Retreat

2. Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy

3. Colorful getaway in friendly Driftless village

4. Hillsboro Driftless Guesthouse is cozy and ready for you!

5. Yukon Trails RV & Camping Resort

6. Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!

7. Your adventure begins the second you arrive!

8. A Comfy Cozy Cottage on Clowney

9. Cabin on the Kickapoo

10. Serenity Cottage at Mineral Point

11. Peaceful Country Comfort W Panoramic Views of Big Creek Valley

12. Rustic Hideaway Sleeps 4 HOT TUB

13. Ohio Street Retreat-hot tub, pool, massage chair

14. The Bungaleau 1 Bedroom House In Cute Rivertown

15. Arrowhead Resort Campground

16. Arbor Acres Cottage! Bright, cheery, cozy and ready for you right by Wis Dells!

17. The Docksider - Couples & Young Families - Lakefront!

18. Peyton's Place at Tamarack - Great Location!

19. Quiet And Beautiful!!

20. Tiny House on the River

Find holiday rentals that suit your style

Top Southwest Wisconsin Hotel Reviews

Dellshire Resort

Find out more about Southwest Wisconsin

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