Gentryville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Gentryville Vacation
Take away the hard part of organizing your next great adventure with a Gentryville vacation package. Whether you're here for its cuisine, history, art or other highlights, you'll find countless exciting experiences to delve into. You'll want to take in some sights during your trip to Gentryville. Carve out some time for top attractions such as Lincoln Boyhood National Memorial, Colonel William Jones Home and Antique Shak. Whatever your travel plans or budget, organizing your ultimate tailored Gentryville vacation is a breeze with Expedia.
Ready to book your vacation to Gentryville?
Gentryville Hotel Deals
The Family Oasis just 6 miles from Holiday World
Gentryville IN
9.4/10 Exceptional! (56 reviews)
"Booked this house for our short stay for holiday world. This house isn’t extravagant by any means but just what we needed for a short stay with our family. So close to holiday world and got the best pizza from Hoosier pizza and wings!"
Reviewed on Aug 22, 2026
The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville IN
CA $153
CA $528 total
Sep 29 - Sep 30
includes taxes & fees
10/10 Exceptional! (1 review)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
Reviewed on Aug 11, 2026
Another Oasis just 6 miles from Holiday World
Gentryville IN
9/10 Wonderful! (33 reviews)
"Very spacious, great location and easy access to the house. One bathroom is pretty small. Kitchen has only cooking and eating utensils - bring everything else you need."
Reviewed on Sep 2, 2026
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.
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 many days is enough for Gentryville?
The ideal duration for your Gentryville vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the main attractions and explore some hidden treasures along the way.
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 travellers 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?
- Pick your dates: What you want to do in Gentryville and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
