Southwestern Indiana Vacation Packages 2026 from $638

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Your Southwestern Indiana Vacation

Leave the travel planning to us with a Southwestern Indiana vacation package. With everything organized before you leave home, the only thing you'll need to do is sit back, relax and experience this destination's culture and charm. With so many things to see on a trip to Southwestern Indiana, it can be difficult to know where to start. Kick off your journey in Evansville at Ford Center and Bally's Evansville Casino — two popular attractions here. Another city to add to your itinerary is Jasper. Be sure not to miss Sultan's Run Golf Course and Jasper City Mill. Expedia is your one-stop shop when it comes to organizing your Southwestern Indiana vacation. From flights and hotels, to activities and more, we're here to help you create a travel experience like no other.

The Latest Southwestern Indiana vacation packages

Price found within the past 48 hours. Click for updated prices.

Howard Johnson by Wyndham Evansville East

$638

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Evansville (EVV)

8/10 Very Good! (1,002 reviews)

New Harmony Inn Resort and Conference Center

$794

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Evansville (EVV)

9/10 Wonderful! (547 reviews)

Very calm place. The town is a very quiet, peaceful place as well. If you are looking for a getaway where you just want to relax maybe take a bike ride or a nice walk. Do a little shopping in an adorable downtown. Enjoy a good meal this is the place for it.

Reviewed on Aug 9, 2026

Residence Inn by Marriott Evansville East

$774

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Evansville (EVV)

8.6/10 Excellent! (553 reviews)

Holiday Inn Express Evansville West by IHG

$871

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Evansville (EVV)

8.6/10 Excellent! (596 reviews)

Simply Home Inn & Suites

$756

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Chicago (CHI) to Evansville (EVV)

7/10 Good! (8 reviews)

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Stay near popular Southwestern Indiana attractions

A water slide with a yellow and green inflatable raft carrying three people.

Holiday World and Splashin' Safari

9.4/10 (294 reviews)

Every day is a holiday at this fun-filled combination theme park and water park, where visitors of all ages can explore roller coasters, raft rides and wave pools.

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A leopard lying on grass with a chain-link fence in the background.

Mesker Park Zoo

8.0/10 (158 reviews)

Meet the animals who live at Mesker Park Zoo during your trip to Evansville. While you're here, you can savor the lively bars.

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Ford Center

8.4/10 (472 reviews)

Catch an event at Ford Center during your trip to Evansville. While you're here, you can savor the lively bars.

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Ellis Park Race Course

8.4/10 (27 reviews)

Why not roll the dice with a visit to Ellis Park Race Course during your time in Henderson? Stroll along the riverfront or experience the festivals in this family-friendly area.

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Deaconess Sports Park

8.4/10 (31 reviews)

Deaconess Sports Park is just one of the places to see in Evansville, so why not enjoy the other things to explore during your travels? Check out the shops and top-notch restaurants in this family-friendly area.

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Old National Events Plaza

8.2/10 (122 reviews)

Catch an event at Old National Events Plaza during your trip to Evansville. While you're here, you can savor the lively bars.

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Vincennes University

8.6/10 (77 reviews)

Take a campus tour or just explore the area of Vincennes University, during your trip to Vincennes. Discover the entertainment venues and cathedral in this family-friendly area.

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Eastland Mall

8.4/10 (503 reviews)

You can browse for the perfect souvenirs at Eastland Mall during your trip to Evansville. Attend a sporting event while you're in the area, or simply enjoy its cocktail bars.

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Southwestern Indiana Hotel Deals

Santas Lodge and Resort

91 W CHRISTMAS BLVD Santa Claus IN

Fully refundableReserve now, pay when you stay

$111 nightly

$124 total

Aug 17 - Aug 18

Total with taxes and fees

8/10 Very Good! (407 reviews)

"Nice"

Reviewed on Aug 10, 2026

Jasper Inn

951 Wernsing Road Jasper IN

Fully refundableReserve now, pay when you stay

$81 nightly

$91 total

Aug 17 - Aug 18

Total with taxes and fees

8/10 Very Good! (806 reviews)

"Adequate. The rooms weren't as clean as one might like and the bathroom desperately needed updating. The breakfast was a little below average for a hotel hot breakfast."

Reviewed on Aug 9, 2026

Bally’s Evansville Casino & Hotel

421 NW Riverside Drive Evansville IN

Fully refundableReserve now, pay when you stay

$86 nightly

$99 total

Aug 17 - Aug 18

Total with taxes and fees

See all 401 properties in Southwestern Indiana

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.