Southwestern Indiana Romantic Vacations

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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

Howard Johnson by Wyndham Evansville East

$631
per person
Oct 8 - Oct 12
found 18 hours ago
Roundtrip non-stop flight included
Sarasota (SRQ) to Evansville (EVV)
8/10 Very Good! (1,002 reviews)
The rooms were dirty with stains on the chairs and bed. We had to switch to a different room then the pillows had hair on it. Not my hair. There was a crack in the bathtub. You only allowed two towels which are tiny and rough. Over half the outlets in the room didn’t work including the charging outlets to charge your phone. The rooms smelled. We tried three of them.

Reviewed on Aug 12, 2026

Drury Inn & Suites Evansville East

Drury Inn & Suites Evansville East

$743
per person
Oct 8 - Oct 12
found 18 hours ago
Roundtrip non-stop flight included
Sarasota (SRQ) to Evansville (EVV)
9.4/10 Exceptional! (1,008 reviews)
Hilton Garden Inn Evansville

Hilton Garden Inn Evansville

$743
per person
Oct 8 - Oct 12
found 18 hours ago
Roundtrip non-stop flight included
Sarasota (SRQ) 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 to find a romantic Southwestern Indiana vacation

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 and visiting outside busy months of .

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 $631. Stay during the quiet season, in , for breaks to make your bank balance smile. 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.

What’s the best time of year for a romantic vacation in Southwestern Indiana?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

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

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.
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
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 ...
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
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 ...
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.