Southwestern Indiana Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Packages with flights are ATOL protected

How to find a romantic Southwestern Indiana holiday

How can I find the best Southwestern Indiana vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southwestern Indiana. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Southwestern Indiana romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southwestern Indiana that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southwestern Indiana romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Southwestern Indiana?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Southwestern Indiana?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Southwestern Indiana that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Southwestern Indiana with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Southwestern Indiana romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Southwestern Indiana Hotels

Drury Inn & Suites Evansville East

Drury Inn & Suites Evansville East

3 out of 5
100 Cross Pointe Blvd Evansville IN
  • 1 hour drive from Holiday World and Splashin' Safari
Stay at this business-friendly hotel in Evansville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,000 reviews)
The rooms were clean and appeared well maintained. They are on the smaller side as are many of the amenities at this property. The staff was friendly and check in was quick and easy. The lobby is microscopic as is the breakfast/happy hour area. We have stayed at many Drury Inns over the years and ...

Reviewed on 10 May 2026

Drury Inn & Suites Evansville East
Baymont by Wyndham Dale

Baymont by Wyndham Dale

2.5 out of 5
1339 N Washington St Dale IN
  • 15 min drive from Holiday World and Splashin' Safari
Stay at this business-friendly hotel in Dale. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the clean rooms and the property condition ...
6.8/10 (1,003 reviews)
Tv channels terrable....breakfast was pathetic.....supposed to be a hot breakfast..no eggs no bacon no sausage...milk was luke warm.....used to be great place..but must be under different management..and it terrable now

Reviewed on 12 May 2026

Baymont by Wyndham Dale
Bally’s Evansville Casino & Hotel

Bally’s Evansville Casino & Hotel

3 out of 5
421 NW Riverside Drive Evansville IN
  • 2 hours drive from Holiday World and Splashin' Safari
Stay at this business-friendly hotel in Evansville. Enjoy free Wi-Fi, free parking and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,298 reviews)
The room was a nice size, clean, and a comfortable bed. I knocked down 1 star for hotel cleanliness because the carpets from the casino and parking area to the hotel were very soiled. The parking garage is not convenient to hotel guest. You have to walk through the garage to the entrance to the casino ...

Reviewed on 12 May 2026

Bally’s Evansville Casino & Hotel
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. Flight-inclusive packages are ATOL protected.