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

Search Chalets in Southwest Wisconsin

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Southwest Wisconsin chalets

Outdoor dining

NEW OWNR SPECL - Hilltop Oasis w/ HotTub+Sauna-Close to Wis Dells & Baraboo!

NEW OWNR SPECL - Hilltop Oasis w/ HotTub+Sauna-Close to Wis Dells & Baraboo!
Portage
10.0 out of 10, Exceptional, (14 reviews)
"The host was excellent. Location was perfect. "
United States
Jamie H.
NEW OWNR SPECL - Hilltop Oasis w/ HotTub+Sauna-Close to Wis Dells & Baraboo!
Terrace/patio

Lakefront-Bar-Arcade-30 min to WI Dells-Water Toys

Lakefront-Bar-Arcade-30 min to WI Dells-Water Toys
Friendship
10.0 out of 10, Exceptional, (10 reviews)
"Stayed for the weekend with several families and had a great time playing games, relaxing and enjoying the view!"
United States
Katheryn M.
The price is SAR 2,737
SAR 4,825 total
includes taxes & fees
31 Jul - 1 Aug
Lakefront-Bar-Arcade-30 min to WI Dells-Water Toys
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

Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

10/10 Excellent
"the room smells like marihuana when we got inside, but I open the window and the smell leaves"
Lila 2-night trip
Posted 2 hours ago
Baymont by Wyndham Madison West/Middleton WI West

Explore a world of travel with Expedia