Southwest Wisconsin Vacations from $302

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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.
Hotel Riu Plaza Chicago
Level Chicago – Old Town
Hotel Felix River North/Magnificent Mile
Hilton Chicago O'Hare Airport
theWit Chicago, a Hilton Hotel
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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

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 Jan 18 to Jan 19
$161 total
Jan 18 - Jan 19
Total with taxes and fees
9.4/10 Exceptional! (3,427 reviews)
This was a great place to stay! The room was clean & spacious. The location is close to everything downtown Madison. The weather wasn’t great & the hotel has a shuttle service that will take you most anywhere you want to go. The bar & bartender Dallas were awesome! Dallas gave us great recommendations ...

Reviewed on Jan 4, 2026

The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Jan 12 to Jan 13
$122 total
Jan 12 - Jan 13
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Great amenities and really friendly staff.

Reviewed on Jan 9, 2026

DoubleTree by Hilton Madison East
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $84 total per night from Jan 19 to Jan 20
$84 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
The front dest staff were exceptional, always a smiling face and a welcoming greeting. The room was clean and comfortable. I am confused about the billing. I was charged, but also credited for more than the charge of the room.

Reviewed on Jan 3, 2026

Hampton Inn & Suites Madison-West
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.

Find the Best Southwest Wisconsin Vacation Packages

Things to do near Southwest Wisconsin

Southwest Wisconsin offers a perfect blend of outdoor adventures and scenic beauty, making it ideal for romantic getaways. Visitors can explore great bike trails and enjoy scenic trips while discovering numerous camping spots and hiking trails. With recreational areas and campgrounds available, there's plenty to do for nature lovers looking to immerse themselves in the stunning landscapes of this charming region.

Shopping

For unique gifts, visit The Red Geranium Framing and Gifts, located 30 miles from Southwest Wisconsin. Closer at 19 miles, the Viking Village Shopping Center offers a mix of entertainment and family-friendly shopping. Don’t miss the Spring Green General Store, just 20 miles away, for local specialties.

Recreation

West Side Park, a family-friendly playground 6 miles from Southwest Wisconsin, offers a vibrant outdoor atmosphere. For a more serene experience, visit Sauk County Forest, 17 miles away, perfect for wellness and relaxation. Fireman's Park, located 16 miles from the area, also provides a tranquil setting for recreation.

Adventure

At Miner Hill Trails Park, hike scenic trails surrounded by nature, located 5 miles from Southwest Wisconsin. The 400 State Trail offers breathtaking views and adventure within 14 miles. For a longer trek, explore Meadow Valley Trailhead, a stunning hiking destination 28 miles away, perfect for outdoor enthusiasts.

Nightlife

Experience the vibrant nightlife in Southwest Wisconsin by visiting the lively bars in Madison or the charming taverns in Prairie du Chien. Enjoy live music at local venues or unwind with friends at cozy breweries, embracing the friendly atmosphere that defines this region's evening entertainment.

*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 offers a perfect blend of outdoor adventures, stunning scenery, and romantic getaways. Explore urban parks, nature preserves, and captivating caves, ideal for family outings and cultural experiences. Don't miss the picturesque Wisconsin River Valley and its state parks, or the famous Wisconsin Dells, ensuring an unforgettable trip filled with natural beauty and recreational activities.

  • A.D. German Warehouse: Explore the remarkable A.D. German Warehouse, an architectural gem located 6 miles from Southwest Wisconsin. This historic site exudes cultural vibes and showcases the region's rich heritage, making it a must-visit for history buffs and architecture enthusiasts alike.
  • Eagle Cave: Experience the thrill of adventure at Eagle Cave, situated 15 miles away. This captivating cave offers outdoor exploration opportunities, perfect for those who love hiking, spelunking, and discovering natural wonders in a breathtaking setting.
  • Pier County Park: Enjoy the serene beauty of Pier County Park, just 4 miles from Southwest Wisconsin. This picturesque reserve is ideal for picnicking, hiking, and immersing yourself in the tranquility of nature, making it a perfect spot for relaxation and outdoor activities.

Best time to go to Southwest Wisconsin

The best time to visit Southwest Wisconsin is dependent 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 cloudy with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January18.0°F (-7.800000000000001°C)No RainMostly CloudyModerately LowSlightly Low
February20.7°F (-6.300000000000001°C)No RainMostly CloudyModerately LowAverage
March34.7°F (1.5°C)Light RainMostly CloudyAverageSlightly Low
April44.1°F (6.7°C)Light RainMostly CloudyAverageAverage
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 RainMostly CloudyModerately 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 during the off-peak season (typically March and December to January) for more affordable package holidays to Southwest Wisconsin.
  • 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.

Southwest Wisconsin Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)

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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.