Southwestern Indiana Romantic Vacations 2026

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4 Night Romantic vacations in Southwestern Indiana

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

Howard Johnson by Wyndham Evansville East

$559

per person

Sep 18 - Sep 22

found 10 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Evansville (EVV)

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

Everything was great

Reviewed on Aug 8, 2026

Drury Inn & Suites Evansville East

$681

per person

Sep 18 - Sep 22

found 10 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Evansville (EVV)

9.4/10 Exceptional! (1,005 reviews)

We booked a one bedroom suite to give our family more space. Nice layout and very clean. No lock on the bedroom door which would have been appreciated. The hotel offers one free alcoholic drink per evening that you are staying there. Honestly this just created more of a bar atmosphere. When you're traveling with kids that's the last thing I want to deal with.

Reviewed on Aug 9, 2026

Hilton Garden Inn Evansville

$678

per person

Sep 18 - Sep 22

found 10 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Evansville (EVV)

8.8/10 Excellent! (758 reviews)

The breakfast to me was for consumption. There were children playing in the fruit with their hands,the bacon was over cooked and there was a $14 charge for the buffet. The cashier was very nice and only charged for what we got. The room was very nice.

Reviewed on Aug 9, 2026

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Southwestern Indiana romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Southwestern Indiana?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Southwestern Indiana?

Put a price on love with stunning deals for duos starting at just $559. Prices and availability are subject to change. Additional terms may apply.

Can I book Southwestern Indiana spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Southwestern Indiana?

To book a loved-up break in Southwestern Indiana, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

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

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Southwestern Indiana Hotels

Drury Inn & Suites Evansville East

100 Cross Pointe Blvd Evansville IN

1 hour drive from Holiday World and Splashin' Safari

A hot tub and more await visiting couples at this romantic hotel.

9.4/10 Exceptional! (1,003 reviews)

"We booked a one bedroom suite to give our family more space. Nice layout and very clean. No lock on the bedroom door which would have been appreciated. The hotel offers one free alcoholic drink per evening that you are staying there. Honestly this just created more of a bar atmosphere. When you're ..."

Reviewed on Aug 9, 2026

Baymont by Wyndham Dale

1339 N Washington St Dale IN

15 min drive from Holiday World and Splashin' Safari

Book a stay at this business-friendly hotel in Dale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms and the property condition ...

6.8/10 (1,025 reviews)

"More clean de rooms and the bathroom too small"

Reviewed on Aug 9, 2026

Bally’s Evansville Casino & Hotel

421 NW Riverside Drive Evansville IN

2 hours drive from Holiday World and Splashin' Safari

Rekindle the spark in your relationship. Book a romantic getaway at this hotel where you and your special someone are sure to love the 3 restaurants and 2 ...

7.8/10 Good! (1,292 reviews)

"The facility was filthy, smoking in the casino. Cavanah's on the River was the highlight of the weekend."

Reviewed on Aug 9, 2026

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.