Gentryville Vacations from $655
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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.
The Latest Gentryville vacation packages
Price found within the past 48 hours. Click for updated prices.
New Harmony Inn Resort and Conference Center
$798
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Evansville (EVV)
9/10 Wonderful! (549 reviews)
New Harmony Inn starts out at an advantage. It is basically the northern demarcation of a lovely destination. The grounds are peaceful and surrounded by nature or history wherever you look. You can rent golf carts to explore the town or many of the trails. The rooms are quiet and well-appointed. I did not eat at the Red Geranium this trip since it's hours didn't align with my visit. However, past experience was phenomenal, both in quality of food and in service.
Reviewed on Aug 24, 2026
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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.
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
Another Oasis just 6 miles from Holiday World
Gentryville IN
9/10 Wonderful! (32 reviews)
"Very close to Holiday World and lots of space for a large family group"
Reviewed on Aug 16, 2026
The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville IN
$349 nightly
$391 total
Aug 27 - Aug 28
Total with taxes and 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
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.
Find the Best Gentryville Vacation Packages
Gentryville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Owensboro-Daviess County Regional Airport (OWB) |
Top Sights | Colonel William Jones Home, Lincoln Boyhood National Memorial and Antique Shak |
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Frequently asked questions
How much does a Gentryville vacation package cost?
Offering excellent value package deals from $655 on Expedia, you'll be surprised at how little a vacation to Gentryville costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Gentryville?
If you'd like to book a cheap Gentryville vacation package, consider visiting in December, January and February. You'll generally find better prices on hotels and airfares during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Gentryville?
The ideal length of your Gentryville vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to visit all the major attractions and discover some hidden spots along the way.
How to find the best Gentryville package deals?
Use Expedia's handy filters to find some great Gentryville package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Gentryville package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Gentryville vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Gentryville vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Gentryville?
Enjoy incredible discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Gentryville adventure.
Does Expedia offer Book Now, Pay Later Gentryville vacation packages?
Your Gentryville break should be an escape from your daily routine, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
