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Southern Wisconsin Vacations from $569
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The Latest Southern Wisconsin Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Wildwood Lodge
Oct 7 - Oct 12Wildwood Lodge + Flight
Pewaukee5 nights2.5 star property9.0/10 - Wonderful (1,056 reviews)Roundtrip • Dallas (DFW) - Milwaukee (MKE)DFW - MKE • Nonstop MKE - DAL • 1 stop$709$569found 4 hours agoper traveler - The Pfister Hotel
Oct 9 - Oct 12The Pfister Hotel + Flight
Downtown Milwaukee3 nights4.5 star property9.6/10 - Exceptional (2,194 reviews)"An elevated level of quality and service. From breakfast at the cafe, Blu bar, lobby bar, check in and out- amazing. The only thing I can think of that could be improved were our waters were not replenished after day 1 in our room. (Minor, and we did not follow up and ask for any). Champagne at check in and waters for the road. We hadn’t stayed here in years and will be back sooner rather than later!"Reviewed August 2, 2026Roundtrip • Chicago (CHI) - Milwaukee (MKE)MDW - MKE • Nonstop MKE - MDW • Nonstop - Kimpton Journeyman Hotel by IHG
Oct 7 - Oct 12Kimpton Journeyman Hotel by IHG + Flight
Downtown Milwaukee5 nights4.5 star property9.4/10 - Exceptional (1,002 reviews)"❤️"Reviewed August 3, 2026Roundtrip • Dallas (DFW) - Milwaukee (MKE)DFW - MKE • Nonstop MKE - DAL • 1 stop$1,405$1,130found 1 day agoper traveler - The Iron Horse Hotel
Oct 23 - Oct 25The Iron Horse Hotel + Flight
Fifth Ward2 nights4.0 star property9.2/10 - Wonderful (1,266 reviews)"Perfect stop for a short visit"Reviewed August 2, 2026Roundtrip • Dallas (DFW) - Milwaukee (MKE)DFW - MKE • Nonstop MKE - DFW • 1 stop$699$572found 1 day agoper traveler - Saint Kate - The Arts Hotel
Sep 25 - Sep 27Saint Kate - The Arts Hotel + Flight
Downtown Milwaukee2 nights4.0 star property9.8/10 - Exceptional (2,653 reviews)Roundtrip • Atlanta (ATL) - Milwaukee (MKE)ATL - MKE • Nonstop MKE - ATL • Nonstop$1,198$983found 1 day agoper traveler
Discover the most popular places to visit in Southern Wisconsin
Southern Wisconsin Hotel Deals
Comfort Suites Johnson Creek Conference Center
Comfort Suites Johnson Creek Conference Center2.5 star property
43.9 mi from Southern Wisconsin
8.2 out of 10, Very Good, (1,005 reviews)
8.2/10
Very Good
(1,005 reviews)
$86 nightly
The price is $97
$97 total
Aug 9 - Aug 10
Total with taxes and fees
Prairie Inn and Suites Holmen/La Cross
Prairie Inn and Suites Holmen/La Cross2.0 star property
93 mi from Southern Wisconsin
9.0 out of 10, Wonderful, (934 reviews)
9.0/10
Wonderful
(934 reviews)
"Everything was great"
$69 nightly
The price is $76
$76 total
Aug 6 - Aug 7
Total with taxes and fees
9.2 out of 10, Wonderful, (700 reviews)
9.2/10
Wonderful
(700 reviews)
"Great place to stay."
$111 nightly
The price is $124
$124 total
Aug 4 - Aug 5
Total with taxes and fees
Sleep Inn & Suites Oregon - Madison
Sleep Inn & Suites Oregon - Madison2.5 star property
36.4 mi from Southern Wisconsin
9.4 out of 10, Exceptional, (441 reviews)
9.4/10
Exceptional
(441 reviews)
"Clean"
$74 nightly
The price is $84
$84 total
Aug 30 - Aug 31
Total with taxes and fees
Quality Inn & Suites Lodi I-90
Quality Inn & Suites Lodi I-902.5 star property
7.4 mi from Southern Wisconsin
8.8 out of 10, Excellent, (1,009 reviews)
8.8/10
Excellent
(1,009 reviews)
"We were very satisfied with our entire stay. The staff was welcoming. The room was clean and even smelled clean. The beds were comfortable. The bathroom and shower were nice and had plenty of amenities. The breakfast was good, hot and plentiful. My son liked the waffle station with the chocolate chips and sprinkles. The pool and jacuzzi were well maintained and clean. I would definitely stay again."
$76 nightly
The price is $80
$80 total
Aug 6 - Aug 7
Total with taxes and fees
GrandStay Hotel & Suites Mount Horeb - Madison
GrandStay Hotel & Suites Mount Horeb - Madison3.0 star property
31.1 mi from Southern Wisconsin
9.2 out of 10, Wonderful, (903 reviews)
9.2/10
Wonderful
(903 reviews)
$128 nightly
The price is $145
$145 total
Sep 2 - Sep 3
Total with taxes and fees
9.2 out of 10, Wonderful, (970 reviews)
9.2/10
Wonderful
(970 reviews)
"This hotel is overpriced. On the plus side, the room was quiet and comfortable. The bar area was nice and any sound from there did not make it to our room, three doors down. Negatives are no cleaning unless you request it, and the sign that was supposed to be in the room to that effect was missing. Breakfast was only fair for the room price. Just above continental with eggs and biscuits and gravy (not even any bacon). I would not stay here again unless the room rate drops significantly."
$125 nightly
The price is $140
$140 total
Aug 9 - Aug 10
Total with taxes and fees
AmericInn by Wyndham West Salem
AmericInn by Wyndham West Salem3.0 star property
84.5 mi from Southern Wisconsin
8.6 out of 10, Excellent, (1,002 reviews)
8.6/10
Excellent
(1,002 reviews)
$72 nightly
The price is $80
$80 total
Aug 23 - Aug 24
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.