Southwestern Indiana Romantic Holidays

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

Photo by Jamie Stacy
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  • Rest easy

    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

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 ...
Drury Inn & Suites Evansville East
Baymont by Wyndham Dale

Baymont by Wyndham Dale

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 (1,028 reviews)
"Went as a group with 2 bookings. At check in they told us we had to move to another hotel managed by the same company. They said there was a maintenance issue with one of the rooms. Would have been nice to know before driving 4 hours to the hotel. They gave us a $100 discount for the stay, only come ..."

Reviewed on 11 Aug 2026

Baymont by Wyndham Dale
Bally’s Evansville Casino & Hotel

Bally’s Evansville Casino & Hotel

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 ...
Bally’s Evansville Casino & Hotel
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.

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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.