A lake surrounded by lush green hills and a rocky cliff.

Southwest Wisconsin Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southwest Wisconsin vacation rentals

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

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

Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
2.0 star property
Wild Rose
9.8 out of 10, Exceptional, (146 reviews)
"We liked everything during our stay and we'll definitely be back."
United States
Jennifer
$141 nightly
The price is $149
Nov 5 - Nov 6
Total with taxes and fees
Postcard Cabins Wild Rose, Outdoor Collection by Marriott Bonvoy
A wooden cabin with a porch, two windows, and a star decoration on the wall.

2. River Road Retreat

River Road Retreat
Muscoda
9.8 out of 10, Exceptional, (32 reviews)
"We had a great stay"
United States
Robert S.
$206 nightly
The price is $217
Oct 7 - Oct 8
Total with taxes and fees
River Road Retreat
A compact kitchen with a built-in stove, a microwave, and a large TV.

3. Arrowhead Resort Campground

Arrowhead Resort Campground
2.0 star property
Wisconsin Dells
7.8 out of 10, Good, (47 reviews)
"Clean, well maintained cottage. Comfy beds. Super close to downtown activities."
United States
Alexis
$125 nightly
The price is $132
Oct 7 - Oct 8
Total with taxes and fees
Arrowhead Resort Campground
A beach with sun loungers and a view of a lake.

4. Top Floor Retreat at Delton Grand

Top Floor Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (43 reviews)
"Everything was good. Definitely would stay again. "
United States
Matt J.
$188 nightly
The price is $211
Oct 7 - Oct 8
Total with taxes and fees
Top Floor Retreat at Delton Grand
A lakeside view with beach chairs and a dock.

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

The Docksider - Couples & Young Families - Lakefront!
Lake Delton
10.0 out of 10, Exceptional, (235 reviews)
"The Lake Delton Docksider condo was clean, comfortable, and located close to all Wisconsin Dells attractions. We enjoyed sitting on the balcony and watching the boats pass by. Communication with the property manager was great and we had no issues."
United States
Tom T.
$177 nightly
The price is $198
Oct 8 - Oct 9
Total with taxes and fees
The Docksider - Couples & Young Families - Lakefront!
A living room with a television, a coffee table, a sofa, and a dining area in the background.

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

Hillsboro Driftless Guesthouse is cozy and ready for you!
Hillsboro
10.0 out of 10, Exceptional, (31 reviews)
"The property is very well maintained, house was very cozy and relaxing. The host was great to communicate with."
United States
Tammy
$204 nightly
The price is $215
Oct 7 - Oct 8
Total with taxes and fees
Hillsboro Driftless Guesthouse is cozy and ready for you!
A waterfront hotel with multiple buildings, a dock, and a swimming pool.

7. Sandy Toes at Lighthouse Cove

Sandy Toes at Lighthouse Cove
Lake Delton
9.8 out of 10, Exceptional, (35 reviews)
"Very nice condo, very clean and comfortable. Convenient to all atractions."
United States
Katherine A.
$171 nightly
The price is $192
Oct 7 - Oct 8
Total with taxes and fees
Sandy Toes at Lighthouse Cove
A lakeside view with a dock, picnic tables, and chairs.

8. Piers & Pines at Island Pointe

Piers & Pines at Island Pointe
Wisconsin Dells
10.0 out of 10, Exceptional, (33 reviews)
"Wonderful stay. Perfect little cabin and hosts were very helpful."
United States
Alisia
$194 nightly
The price is $218
Oct 7 - Oct 8
Total with taxes and fees
Piers & Pines at Island Pointe
A waterfront hotel with multiple buildings, a dock, and a swimming pool.

9. Ground Floor at Lighthouse Cove

Ground Floor at Lighthouse Cove
Lake Delton
9.4 out of 10, Exceptional, (19 reviews)
"Very nice place. Great location in the Dells. "
United States
Tracey W.
$184 nightly
The price is $207
Oct 13 - Oct 14
Total with taxes and fees
Ground Floor at Lighthouse Cove
Two white hammocks hanging on a wooden porch with a view of a garden.

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

Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
Lyndon Station
10.0 out of 10, Exceptional, (86 reviews)
"Beautiful property, secluded, and very well maintained."
United States
Eukesha
$313 nightly
The price is $330
Oct 13 - Oct 14
Total with taxes and fees
Charming cabin getaway in the woods, private trails, only 20 mins from WI Dells!
A large indoor swimming pool with a clear view of the pool area, including a poolside seating area and a lifeguard stand.

11. Luxury Beachfront Retreat at Delton Grand

Luxury Beachfront Retreat at Delton Grand
Lake Delton
9.6 out of 10, Exceptional, (23 reviews)
"Extremely clean and accurate property. Owners were quick to respond and it was the perfect get away. Very relaxing and enjoyable location. Loved the direct access with nature and it's close to everything."
United States
TCat C.
$185 nightly
The price is $207
Oct 7 - Oct 8
Total with taxes and fees
Luxury Beachfront Retreat at Delton Grand
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

12. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (55 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$125 nightly
The price is $132
Nov 2 - Nov 3
Total with taxes and fees
A Room with a View
A wooden cabin surrounded by snow-covered trees.

13. Cabin on the Kickapoo

Cabin on the Kickapoo
Readstown
9.6 out of 10, Exceptional, (53 reviews)
"Fun little place. Perfect for me and the wife. Close to Kickapoo area hiking. Hot tub was a nice touch to the neat little stay."
United States
Joel M.
$293 nightly
The price is $318
Oct 18 - Oct 19
Total with taxes and fees
Cabin on the Kickapoo
A beach with sun loungers and a view of a lake.

14. Beachtop Condo at Delton Grand - Waterfront

Beachtop Condo at Delton Grand - Waterfront
Lake Delton
10.0 out of 10, Exceptional, (40 reviews)
"Excellent communication and a wonderful place to stay. My family had a great time, and we would certainly consider returning in the future."
United States
Rishi
$279 nightly
The price is $313
Oct 7 - Oct 8
Total with taxes and fees
Beachtop Condo at Delton Grand - Waterfront
A waterfront hotel with multiple buildings, docked boats, and a surrounding forested area.

15. Dells Lakefront Escape - Couples or Families

Dells Lakefront Escape - Couples or Families
Lake Delton
9.8 out of 10, Exceptional, (37 reviews)
"The view was incredible, amenities were great, location was close to everything, and the host was very responsive!"
United States
Phoenix L.
$182 nightly
The price is $204
Oct 7 - Oct 8
Total with taxes and fees
Dells Lakefront Escape - Couples or Families
A modern kitchen with a central island, stainless steel appliances, and wooden flooring.

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

Ohio Street Retreat-hot tub, pool, massage chair
Prairie du Chien
10.0 out of 10, Exceptional, (95 reviews)
"Was a very nice and quiet place to relax and enjoy. Comfortable beds and very nice interior"
United States
nate k.
$205 nightly
The price is $214
Nov 1 - Nov 2
Total with taxes and fees
Ohio Street Retreat-hot tub, pool, massage chair
A field of lavender with a path leading through it.

17. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
$111 nightly
The price is $117
Oct 12 - Oct 13
Total with taxes and fees
Tamarack Point Homestead
A spacious living room with a fireplace, comfortable seating, and large windows offering a view.

18. Harrison's Hideaway at Tamarack - Great Location!

Harrison's Hideaway at Tamarack - Great Location!
Wisconsin Dells
9.8 out of 10, Exceptional, (36 reviews)
"Very clean and comfortable, in a great location. We would stay here again!"
United States
Jennifer S.
$281 nightly
The price is $316
Oct 7 - Oct 8
Total with taxes and fees
Harrison's Hideaway at Tamarack - Great Location!
A bedroom with a bed, bedside lamps, a wooden headboard, a small nightstand, and a window with curtains.

19. Grace-Jo @ Tamarack Highland 5

Grace-Jo @ Tamarack Highland 5
Wisconsin Dells
10.0 out of 10, Exceptional, (44 reviews)
"We loved our stay! It was the perfect place for our little family, we especially loved the indoor pool and hot tub! The location is great as well!"
United States
Jess R.
$171 nightly
The price is $192
Oct 7 - Oct 8
Total with taxes and fees
Grace-Jo @ Tamarack Highland 5
A swimming pool with lounge chairs and tables, surrounded by a stone wall and a fence, with a view of a body of water and trees in the background.

20. The Honey Badger Suite at Delton Grand - No Stairs

The Honey Badger Suite at Delton Grand - No Stairs
Lake Delton
9.6 out of 10, Exceptional, (31 reviews)
"Fantastic condo in the perfect location right on the lake. We enjoyed sitting on the balcony and relaxing. Host was very informative and responsive. Highly recommend staying here!"
United States
Niki O.
$208 nightly
The price is $233
Oct 21 - Oct 22
Total with taxes and fees
The Honey Badger Suite at Delton Grand - No Stairs
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwest Wisconsin Hotel Reviews

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

10/10 Excellent
"Great place to stay. Very warm atmosphere. Large comfortable rooms. Staff is very helpful and courteous."
diane 2-night trip
Posted 7 hours ago
Stoney Creek Hotel La Crosse - Onalaska

Find out more about Southwest Wisconsin

Everything you need to know about Southwest Wisconsin vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwest Wisconsin vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwest Wisconsin vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southwest Wisconsin in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southwest Wisconsin rentals

At Expedia, we put the best Southwest Wisconsin vacation 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 vacation.

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.

Explore a world of travel with Expedia