Gentryville Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Gentryville Vacation Packages

Gentryville Hotel Deals

The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World

Gentryville IN
9.2/10 Wonderful! (50 reviews)
"Absolute amazing experience. Everything was clean and ready for my family and I. The host was so sweet and great with communication. We already planning to come back again next year!"

Reviewed on 6 July 2026

Get rates
The Family Oasis just 6 miles from Holiday World
The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park

Gentryville IN
Get rates
The Cowboys Slumber' 2 Mi to Lincoln State Park
Another Oasis just 6 miles from Holiday World

Another Oasis just 6 miles from Holiday World

Gentryville IN
9/10 Wonderful! (25 reviews)
"The location was great, its proximity to Holiday World and Lincoln State Park at this price point was wonderful. The parking area is in good shape and easily accommodated 4 vehicles. We had a group of 8 adults and 3 children so the sleeping arrangements were a little snug but the spacious family ..."

Reviewed on 2 July 2026

Get rates
Another Oasis just 6 miles from Holiday World
See all 124 properties in Gentryville
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.

Stay near popular Gentryville attractions

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.
See properties

Frequently asked questions

How much does a Gentryville vacation package cost?
You'll find cheap prices on Expedia for your Gentryville break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Gentryville costs.
What are the cheapest months to go to Gentryville?
Travel in the low or shoulder season and you're likely to score cheap Gentryville vacation packages. Remember that school vacation periods and local festivals and events can have an impact on prices, so do some research before you go.
How to find the best Gentryville package deals?
Begin your search for a Gentryville package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Gentryville package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Gentryville adventure off to a flying start.
Is it cheaper to book a Gentryville vacation as a package?
You can enjoy significant savings on your next Gentryville getaway by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Gentryville?
Score fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Gentryville break.
How to plan a trip to Gentryville?

  1. Pick your dates: What you want to do in Gentryville and your preferred season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your stay, you'll need to factor in other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that could arise during your trip to Gentryville.
  3. Decide how long to go for: Now that you're more familiar with Gentryville, you can work out the ideal length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Gentryville vacation package.