Deals on vacations and trips to Gentryville

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Top Gentryville hotels deals

The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World

Gentryville IN
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This vacation home features a picnic area, laundry facilities, and barbecue grills.
Kitchen
Washer
Another Oasis just 6 miles from Holiday World

Another Oasis just 6 miles from Holiday World

Gentryville IN
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This vacation home features laundry facilities.
Kitchen
Washer
Hampton Inn & Suites Downtown Owensboro/Waterfront

Hampton Inn & Suites Downtown Owensboro/Waterfront

2.5 out of 5
401 West 2nd Street Owensboro KY
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $125 total per night
$125 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a hair salon are also on offer.
Pool
Breakfast included
Santas Lodge and Resort

Santas Lodge and Resort

2.5 out of 5
91 W CHRISTMAS BLVD Santa Claus IN
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $124 total per night
$124 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
This hotel features an indoor pool and a seasonal outdoor pool. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area and laundry facilities are also provided.
Pool
Breakfast included
Hampton Inn Jasper

Hampton Inn Jasper

2.5 out of 5
355 3rd Ave Jasper IN
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Jan 17 - Jan 18, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and express check-in are also on offer.
Pool
Hot Tub
Clarion Pointe

Clarion Pointe

2.5 out of 5
272 Brucke Strasse Jasper IN
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $80 total per night
$80 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and free perks like self-serve breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a terrace are also on offer.
Pool
Breakfast included
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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.

Popular places to visit

Colonel William Jones Home

You can find out about the history of Gentryville when you stop by Colonel William Jones Home. Take in the jazz scene and countryside in this family-friendly area.

Colonel William Jones Home

Frequently asked questions

How much are vacation packages to Gentryville?
is all you'll need for an exciting break in Gentryville. Bundle your hotel and flights into a Travelocity package and see your savings start to pile up. With such good prices, traveling has never been so accessible.
Where can I get the best vacation package deals for Gentryville?
Travelocity can help you find a great Gentryville package deal. With more than 400 partner airlines and 1,000,000 properties across the world, we know you'll find the perfect combination.
Why should I book my Gentryville vacation bundle with Travelocity?
We have destinations to suit every kind of traveler, first-rate service and round-the-clock customer support. And to top it off, we'll match any cheaper price you come across with our Price Match Guarantee.
Can I save money on my Gentryville car rental if I bundle it with a hotel or flight?
You certainly can — combine your flight, car and hotel into a Gentryville vacation package and you'll save tons. With so much to see in the Gentryville area, having your own ride will make exploring a joy. Once you've slid into the driver's seat, crank up the tunes and cruise toward Churchill Downs, a top sight around 70 mi from Gentryville.
Which airport is best for Gentryville?
Evansville Regional Airport (EVV) is the major airport for visitors jetting to Gentryville. Once you land, you'll be 25 mi west of downtown.
What is there to do in Gentryville?
Enjoy some excellent photo opportunities at Colonel William Jones Home, one of the most well-known attractions in Gentryville. There's a lot more to discover in this great city, so give yourself enough time to experience some of its lesser-known gems.
Where should I stay when visiting Gentryville?
If you're looking for a place to lay your head, consider the The Family Oasis just 6 miles from Holiday World. It's the top pick for many travelers.

Photos of local treasures

Browse Gentryville vacation photos for more inspiration