Gentryville Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.

Top Gentryville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
PT6 INN

PT6 INN

2.5 out of 5
Price was CA $4,304, price is now CA $4,283 per person
CA $4,283
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip flight included
London (YXU) to Evansville (EVV)
4.6/10 (112 reviews)

New Harmony Inn Resort and Conference Center

New Harmony Inn Resort and Conference Center

3 out of 5
Price was CA $4,427, price is now CA $4,367 per person
CA $4,367
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip flight included
London (YXU) to Evansville (EVV)
9/10 Wonderful! (543 reviews)
Beautiful room and property. Friendly staff. Very clean.

Reviewed on Aug 1, 2026

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was CA $4,428, price is now CA $4,413 per person
CA $4,413
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip flight included
London (YXU) to Evansville (EVV)
8.6/10 Excellent! (552 reviews)
Loved showing up to a treat bag of goodies. It was a nice little extra surprise.

Reviewed on Jul 23, 2026

La Quinta Inn & Suites by Wyndham Evansville

La Quinta Inn & Suites by Wyndham Evansville

3 out of 5
Price was CA $4,390, price is now CA $4,377 per person
CA $4,377
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip flight included
London (YXU) to Evansville (EVV)
8.8/10 Excellent! (1,001 reviews)

Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was CA $4,360, price is now CA $4,353 per person
CA $4,353
per person
Sep 11 - Sep 13
found 10 hours ago
Roundtrip flight included
London (YXU) to Evansville (EVV)
7.8/10 Good! (321 reviews)
Great hotel, very clean. Only thing I didn't really like was the fact that the concierge was on a monitor

Reviewed on Jul 22, 2026

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Gentryville Hotel Deals

The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World

Gentryville IN
9.4/10 Exceptional! (54 reviews)
"This was a nice place very quiet and was very close to denny’s, which was the closest restaurant and Wendy’s everything else will be about 15 miles away also very close to Holiday world very convenient. Would recommend anyone to stay. It was clean and the house was very nice. They supplied s’mores ..."

Reviewed on Jul 31, 2026

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The Family Oasis just 6 miles from Holiday World
Another Oasis just 6 miles from Holiday World

Another Oasis just 6 miles from Holiday World

Gentryville IN
9/10 Wonderful! (29 reviews)
"We have 9 people with us and it was comfortable for everyone. Plenty of space and will be visiting again."

Reviewed on Aug 1, 2026

Get rates
Another 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
The price is CA $139 per night from Aug 17 to Aug 18
CA $139
CA $535 total
Aug 17 - Aug 18
includes taxes & fees
The Cowboys Slumber' 2 Mi to Lincoln State Park
See all 122 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 from CA $4,283 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?

  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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.