Southwest Wisconsin Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Southwest Wisconsin

The Dylin by Mint House
Interior entrance

The Dylin by Mint House

4.0 star property
9.2 out of 10, Wonderful, (94)
"Very easy to access parking and get in the building."
The Dylin by Mint House
Bonanza Camping Resort
Seasonal outdoor pool

Bonanza Camping Resort

2.5 star property
7.8 out of 10, Good, (105)
"We enjoyed the overall experience."
Bonanza Camping Resort
Bluegreen Odyssey Dells
Water park

Bluegreen Odyssey Dells

3.5 star property
9.4 out of 10, Exceptional, (155)
"Love this resort! We stay here every year. "
Bluegreen Odyssey Dells
Tamarack Wisconsin Dells a Ramada by Wyndham
Indoor pool, seasonal outdoor pool

Tamarack Wisconsin Dells a Ramada by Wyndham

3.0 star property
9.2 out of 10, Wonderful, (971)
"Great place to stay "
Tamarack Wisconsin Dells a Ramada by Wyndham
Caribbean Club Resort
Premium Loft, 2 Bedrooms, 2 Bathrooms, Lakeside | Exterior

Caribbean Club Resort

3.0 star property
8.0 out of 10, Very Good, (358)
"We were really happy about our stay. The staff was great and the condo was better than we expected and the views were gorgeous. We would like to go back again."
Caribbean Club Resort
Thunderbird Resort Condo
Dock

Thunderbird Resort Condo

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very well located, exactly as described. "
Thunderbird Resort Condo
Arrowhead Resort Campground
Free WiFi

Arrowhead Resort Campground

2.0 star property
7.8 out of 10, Good, (44)
"Clean with super friendly staff. "
The price is ￥18,007
￥18,998 total
includes taxes & fees
Oct 5 - Oct 6
Arrowhead Resort Campground
Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court
Dining

Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court

2.0 star property
9.8 out of 10, Exceptional, (20)
"The Downtowner is clean & spacious in a quiet neighborhood. It is perfect for a family with young kids. The kids especially enjoyed the game room. We would stay here again! "
The price is ￥40,926
￥95,388 total
includes taxes & fees
Oct 6 - Oct 7
Downtown-ULTIMATE Fam & Friend Getaway - Arcade GameRoom- Basketball Court
Wisconsin Dells Cabin in the Woods
Property grounds

Wisconsin Dells Cabin in the Woods

9.8 out of 10, Exceptional, (76)
"Love the property and location. "
The price is ￥17,278
￥40,278 total
includes taxes & fees
Sep 28 - Sep 29
Wisconsin Dells Cabin in the Woods
Cozy 4-bedroom cabin with WiFi, AC in fabulous Wisconsin Dells
Microwave, oven, stovetop, dishwasher

Cozy 4-bedroom cabin with WiFi, AC in fabulous Wisconsin Dells

6.0 out of 10, (1)
"Great location. Overall clean. Dated and old furniture. Kitchen has minimal baking utensils."
Cozy 4-bedroom cabin with WiFi, AC in fabulous Wisconsin Dells
Condos at 530 E. Hiawatha
Premium Condo, 2 Bedrooms, 2 Bathrooms (Jacuzzi Tub in Master Bath) | 2 bedrooms, individually decorated, individually furnished, desk

Condos at 530 E. Hiawatha

4.0 star property
9.0 out of 10, Wonderful, (79)
"We were there for a concert with another couple. The condo was great for our needs. And very close to the Crystal Grand Theatre. We had a very nice couple of days. "
Condos at 530 E. Hiawatha
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
Fridge, microwave, oven, stovetop

Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!

2.0 star property
10.0 out of 10, Exceptional, (19)
"The place was clean, and my family had a wonderful time during our stay."
The price is ￥62,348
￥146,829 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 6 Bedroom less than 10 min walk to Downtown WI Dells! Sleeps 20+!
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
Indoor pool, a heated pool

*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat

9.8 out of 10, Exceptional, (165)
"very nice place to stay. we will stay again"
The price is ￥15,724
￥45,053 total
includes taxes & fees
Oct 26 - Oct 27
*Pool/Hot Tub| Cozy 2 BR Condo | Waterfront | Downtown | Riverwalk Retreat
Cabin In The Middle Of 72 Acres ~ Private Swim Pond ~ Memorial Day to Labor Day
Game room

Cabin In The Middle Of 72 Acres ~ Private Swim Pond ~ Memorial Day to Labor Day

9.6 out of 10, Exceptional, (283)
"It was a great stay. "
Cabin In The Middle Of 72 Acres ~ Private Swim Pond ~ Memorial Day to Labor Day
All Decked Out | Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells
Outdoor dining

All Decked Out | Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells

9.8 out of 10, Exceptional, (121)
"Clean, excellent location! Great place!"
The price is ￥36,461
￥82,479 total
includes taxes & fees
Oct 12 - Oct 13
All Decked Out | Arcade Games | Amazing 5 BR | Huge Deck | Fire Pit | Close to Everything WI Dells
Elegant country retreat near Spring Green w expansive views of Driftless Region
Smart TV, DVD player, books

Elegant country retreat near Spring Green w expansive views of Driftless Region

10.0 out of 10, Exceptional, (61)
"This house was lovely and very conveniently located to visit local attractions. "
Elegant country retreat near Spring Green w expansive views of Driftless Region
Adventure Trails
Exterior

Adventure Trails

10.0 out of 10, Exceptional, (42)
"This was quiet and the perfect size for our family of 4. Very clean, and had everything we needed. Would book again!"
Adventure Trails
Riverfront Home w/ Private Dock in Wisconsin Dells
House (3 Bedrooms) | Interior

Riverfront Home w/ Private Dock in Wisconsin Dells

3.0 star property
Riverfront Home w/ Private Dock in Wisconsin Dells
Chula Vista Condo: Resort Perks & Family Fun!
Apartment (2 Bedrooms) | Interior

Chula Vista Condo: Resort Perks & Family Fun!

3.0 star property
Chula Vista Condo: Resort Perks & Family Fun!
Lovely condo with on-site water park, balcony, kitchenette & central AC
Property grounds

Lovely condo with on-site water park, balcony, kitchenette & central AC

8.0 out of 10, Very Good, (17)
"We enjoyed our stay there."
Lovely condo with on-site water park, balcony, kitchenette & central AC
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

Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

10/10 Excellent
"Always a great stay for the Wisconsin football games. "
Rebecca 1-night trip
Posted 22 hours ago
Best Western Plus InnTowner Madison

Find out more about Southwest Wisconsin

Find out more about Southwest Wisconsin

Search for holiday rentals in Southwest Wisconsin on Expedia! You can easily find your home rentals, villas, holiday apartments in Southwest Wisconsin using one of the methods below:

  • View our selection of featured holiday rentals in Southwest Wisconsin
  • Use the map to find apartments and other holiday homes in the Southwest Wisconsin neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southwest Wisconsin while they last

Look no further and take a look at our great range of rental properties in Southwest Wisconsin!