Southeast Wisconsin Vacations from $305

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Your Southeast Wisconsin Vacation

Our Southeast Wisconsin vacation packages provide an affordable, easy and immersive way to enjoy everything this exciting destination has to offer. If it's distilleries and craft breweries and dining you're yearning for, this is the place to come. With so many things to see and do on a trip to Southeast Wisconsin, it can be tricky to know where to begin. Kick off your journey in Milwaukee at American Family Field and Wisconsin State Fair Park — two much-loved attractions here. Another top city worth adding to your itinerary is Lake Geneva. Be sure not to miss Geneva Lake and Walworth County Fairgrounds. Expedia has everything you need for planning your Southeast Wisconsin vacation. From accommodations and flights, to car rentals and activities, we know how to curate a travel experience like no other.

The Latest Southeast Wisconsin vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
The Langham, Chicago
Hotel Riu Plaza Chicago
Hilton Garden Inn Naperville/Warrenville
La Banque Hotel
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Where to stay in Southeast Wisconsin

Find the best Southeast Wisconsin areas and neighborhoods for the activities you enjoy most. Learn more about Southeast Wisconsin

Discover the most popular places to visit in Southeast Wisconsin

Southeast Wisconsin Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $187 total per night from Sep 1 to Sep 2
$187 total
Sep 1 - Sep 2
Total includes taxes and fees
9/10 Wonderful! (1,214 reviews)
"convenient location to downtown Lake Geneva. Friendly staff"

Reviewed on Aug 11, 2025

Harbor Shores on Lake Geneva
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
$205 nightly
The price is $242 total per night from Sep 3 to Sep 4
$242 total
Sep 3 - Sep 4
Total includes taxes and fees
9.4/10 Exceptional! (1,686 reviews)
"Excellent option for couples"

Reviewed on Aug 10, 2025

The Pfister Hotel
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$233 nightly
The price is $260 total per night from Aug 14 to Aug 15
$260 total
Aug 14 - Aug 15
Total includes taxes and fees
8.6/10 Excellent! (2,936 reviews)
"We can never have a bad stay at Timber Ridge, amazing family friendly waterpark, great restaurants on both properties, and amazing amenities."

Reviewed on Aug 12, 2025

Timber Ridge Lodge and Waterpark
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.