Southwest Wisconsin Vacations from $336

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Your Southwest Wisconsin Vacation

Choose a vacation package to Southwest Wisconsin and make planning your adventure a breeze. With all the details arranged before you leave, you can focus on enjoying every second in this destination. A trip to Southwest Wisconsin wouldn't be complete without experiencing some of its best cities, starting with Wisconsin Dells. A couple of the most popular attractions here include Mt. Olympus Water and Theme Park and Chula Vista Waterparks. La Crosse is another favorite city with Southwest Wisconsin travelers. Visitors to this destination enjoy Oktoberfest Grounds and Onalaska Omni Center. From the moment you book your Southwest Wisconsin vacation to when you get back home, Expedia will take care of you every step of the way.

The Latest Southwest Wisconsin vacation packages

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites, Lincolnshire by IHG
The Emily Hotel
Chicago Athletic Association, a Hyatt Hotel
Staybridge Suites Chicago O'Hare - Rosemont by IHG
Holiday Inn Chicago O'Hare – Rosemont by IHG
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Where to stay in Southwest Wisconsin

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

Discover the most popular places to visit in Southwest Wisconsin

Southwest Wisconsin Hotel Deals

Mt. Olympus Water & Theme Park Resort

Mt. Olympus Water & Theme Park Resort

3 out of 5
655 N. Frontage Road, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
$45 nightly
The price is $50 total per night from Sep 1 to Sep 2
$50 total
Sep 1 - Sep 2
Total includes taxes and fees
6.8/10 (2,351 reviews)
"Great"

Reviewed on Aug 18, 2025

Mt. Olympus Water & Theme Park Resort
The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $161 total per night from Aug 31 to Sep 1
$161 total
Aug 31 - Sep 1
Total includes taxes and fees
9.4/10 Exceptional! (2,987 reviews)
"walking distance from the Capitol building, restaurants, and bars."

Reviewed on Aug 17, 2025

The Madison Concourse Hotel and Governor's Club
Days Inn & Suites by Wyndham Wisconsin Dells

Days Inn & Suites by Wyndham Wisconsin Dells

2.5 out of 5
2504 Wisconsin Dells Parkway, Wisconsin Dells, WI
Fully refundableReserve now, pay when you stay
$48 nightly
The price is $54 total per night from Sep 7 to Sep 8
$54 total
Sep 7 - Sep 8
Total includes taxes and fees
7/10 Good! (1,514 reviews)
"It was good"

Reviewed on Aug 18, 2025

Days Inn & Suites by Wyndham Wisconsin Dells
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.

Things to do near Southwest Wisconsin

Southwest Wisconsin is a fantastic destination for outdoor enthusiasts, offering a variety of activities such as scenic bike trails, camping spots, and hiking trails. Visitors can enjoy recreational areas and educational experiences, along with opportunities for skiing. Whether you're seeking adventure or simply want to soak in the beautiful scenery, Southwest Wisconsin has something for everyone looking to explore the great outdoors.

Shopping

In Southwest Wisconsin, explore unique finds at the Spring Green General Store, located 20 miles away. For outdoor enthusiasts, WI River Outings, 27 miles out, offers great gear. Don’t miss The Red Geranium Framing and Gifts, 30 miles distant, for charming souvenirs and local art.

Recreation

West Side Park is a vibrant playground perfect for families, offering outdoor fun just 6 miles away. For a tranquil retreat, explore the Sauk County Forest, located 17 miles away, where you can relax amidst nature. Fireman's Park, 16 miles away, provides a peaceful atmosphere for recreation and wellness.

Adventure

Explore the 400 State Trail, a scenic hiking experience 14 miles from Southwest Wisconsin, offering stunning landscapes and adventurous trails. For a closer option, Miner Hill Trails Park, 5 miles away, provides a perfect blend of outdoor fun and beautiful scenery. Don't miss the Meadow Valley Trailhead, 28 miles out, for more hiking excitement.

Nightlife

Southwest Wisconsin boasts a vibrant nightlife with charming taverns and lively venues. Visit The Old Rock Bar for local brews and live music. For a laid-back atmosphere, check out The Blue Room in Prairie du Chien, where you can enjoy cocktails and great company under cozy lights.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Southwest Wisconsin

Southwest Wisconsin is a picturesque destination ideal for outdoor enthusiasts and adventure seekers. Visitors can explore urban parks, nature preserves, and fascinating caves while enjoying family-friendly activities and cultural experiences. Key highlights include the scenic Wisconsin River, the renowned Wisconsin Dells, and the stunning state parks of the Wisconsin River Valley, making it a perfect spot for those looking to immerse themselves in nature's beauty.

  • Krouskop Park: Enjoy a vibrant urban park just 5 miles from Southwest Wisconsin, perfect for family outings and outdoor activities. With its spacious green areas and recreational facilities, it's an ideal spot for picnics, playing sports, or simply soaking up the city vibes.
  • A.D. German Warehouse: Located 6 miles away, this striking architectural gem showcases the rich cultural history of the area. Explore its unique design and learn about its significance through guided tours that delve into its fascinating past.
  • Eagle Cave: Adventure awaits at Eagle Cave, situated 15 miles from Southwest Wisconsin. This natural wonder offers thrilling exploration opportunities, making it a great destination for outdoor enthusiasts and those seeking a little adventure.

Best time to go to Southwest Wisconsin

The best time to visit Southwest Wisconsin is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.800000000000001°C)No RainMostlyModerately LowSlightly Low
February20.7°F (-6.300000000000001°C)No RainMostlyModerately LowAverage
March34.7°F (1.5°C)Light RainMostlyAverageSlightly Low
April44.1°F (6.7°C)Light RainMostlyAverageAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnyModerately HighSlightly High
July71.2°F (21.8°C)Light RainMostly SunnyModerately HighSlightly High
August70.2°F (21.200000000000003°C)Light RainMostly SunnyModerately HighSlightly High
September62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
October49.3°F (9.6°C)Light RainMostly SunnyAverageAverage
November37.6°F (3.1°C)Light RainMostly SunnyAverageAverage
December23.7°F (-4.6000000000000005°C)Light RainMostlyModerately LowSlightly Low

Tips to save on your trip to Southwest Wisconsin

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Southwest Wisconsin during the low season (March and December to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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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.