Title: Gentryville Vacation Packages 2026 from $792 | Expedia.com [Hotels in Gentryville](https://expedia.com/Gentryville-Hotels.d553248634983423194.Travel-Guide-Hotels)[Vacation Rentals in Gentryville](https://expedia.com/Gentryville-Vacation-Rentals.d553248634983423194.Travel-Guide-VacationRentals)[Car Rentals in Gentryville](https://expedia.com/Car-Rentals-In-Gentryville.d553248634983423194.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Gentryville Vacations from $792 ## Book a Hotel + Flight or Car together to unlock savings ## 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](https://www.expedia.com/Lincoln-Boyhood-National-Memorial-Lincoln-City.d6091453.Vacation-Attraction), [Colonel William Jones Home](https://www.expedia.com/Colonel-William-Jones-Home-Gentryville.d553248621532656116.Vacation-Attraction) and [Antique Shak](https://www.expedia.com/Antique-Shak-Dale.d553248621532656117.Vacation-Attraction). 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. ![Envi Boutique Hotel Henderson-Evansville South](https://images.trvl-media.com/lodging/1000000/50000/49800/49726/04b6771f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Envi Boutique Hotel Henderson-Evansville South $792 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip flight included Edmonton (YEA) to Evansville (EVV) 8/10 Very Good! (291 reviews) Room was good but the check in is by internet with a person from another country and it was difficult to understand them. Reviewed on Feb 22, 2026 ![New Harmony Inn Resort and Conference Center](https://images.trvl-media.com/lodging/2000000/1410000/1403900/1403845/3aa51c1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### New Harmony Inn Resort and Conference Center $848 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip flight included Edmonton (YEA) to Evansville (EVV) 9/10 Wonderful! (503 reviews) Very nice facility. Clean, comfortable, great restaurant on site, and very walkable to downtown. Reviewed on Feb 16, 2026 ![Fairfield Inn By Marriott Evansville East](https://images.trvl-media.com/lodging/1000000/10000/8100/8056/0ac226df_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairfield Inn By Marriott Evansville East $807 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip flight included Edmonton (YEA) to Evansville (EVV) 8.8/10 Excellent! (453 reviews) Clean room and friendly staff. Older building but well maintained. Breakfast is the same pre-packaged eggs and meats as other hotel chains. It would be nice to see some fresh options available Reviewed on Mar 4, 2026 ![Holiday Inn Express Princeton by IHG](https://images.trvl-media.com/lodging/1000000/120000/119200/119126/2aff9b14_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Express Princeton by IHG $894 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip flight included Edmonton (YEA) to Evansville (EVV) 8/10 Very Good! (348 reviews) Just a pleasant stay. We had everything we needed. Reviewed on Jan 12, 2026 ![Oakland Courtyard](https://images.trvl-media.com/lodging/118000000/117630000/117625600/117625584/dead24ee_edited_36cc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Oakland Courtyard $895 per person Apr 20 - Apr 24 found 16 hours ago Roundtrip flight included Edmonton (YEA) to Evansville (EVV) 8.4/10 Very Good! (10 reviews) Room very clean and spacious. Bed was comfortable. Reviewed on Feb 7, 2026 Don't see what you're looking for? See all available trips from Columbus to Gentryville [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-05/2026-04-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EVV&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248634983423194) ### Discover the most popular places to visit in Gentryville #### 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. [](https://expedia.com/Colonel-William-Jones-Home-Gentryville.d553248621532656116.Vacation-Attraction) ## Gentryville Hotel Deals ![Another Oasis just 6 miles from Holiday World](https://images.trvl-media.com/lodging/95000000/94390000/94381900/94381850/a3216c5e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Another Oasis just 6 miles from Holiday World Gentryville IN [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=94381850&PinnedHotelID=94381850&HadPinnedHotel=true®ionId=553248634983423194) [](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=94381850&PinnedHotelID=94381850&HadPinnedHotel=true®ionId=553248634983423194) ![The Family Oasis just 6 miles from Holiday World](https://images.trvl-media.com/lodging/52000000/51320000/51313500/51313425/779be0dc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Family Oasis just 6 miles from Holiday World Gentryville IN 9.2/10 Wonderful! (45 reviews) Family getaway to Holiday World There was lots of room for our family to spread out, easy check in, and conveniently located near Holiday World. I was concerned that some of the bar stools and kitchen chairs would break while sitting on them due to wear. The outdoor grill did not work, so we couldn’t grill out. We enjoyed ourselves ... Reviewed on Oct 14, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=51313425&PinnedHotelID=51313425&HadPinnedHotel=true®ionId=553248634983423194) [](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=51313425&PinnedHotelID=51313425&HadPinnedHotel=true®ionId=553248634983423194) ![Hampton Inn & Suites Downtown Owensboro/Waterfront](https://images.trvl-media.com/lodging/7000000/6970000/6963800/6963707/73a9d584_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Downtown Owensboro/Waterfront 401 West 2nd Street Owensboro KY Fully refundableReserve now, pay when you stay $114 nightly $134 total Mar 22 - Mar 23 Total with taxes and fees 9.6/10 Exceptional! (1,001 reviews) ....... Reviewed on Mar 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=6963707&PinnedHotelID=6963707&HadPinnedHotel=true®ionId=553248634983423194) [See all 123 properties in Gentryville](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F6%2F2026&endDate=3%2F7%2F2026®ionId=553248634983423194) 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](https://www.expedia.com/Colonel-William-Jones-Home-Gentryville.d553248621532656116.Vacation-Attraction), [Lincoln Boyhood National Memorial](https://www.expedia.com/Lincoln-Boyhood-National-Memorial-Lincoln-City.d6091453.Vacation-Attraction) and [Antique Shak](https://www.expedia.com/Antique-Shak-Dale.d553248621532656117.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Gentryville vacation package cost? ### What are the cheapest months to go to Gentryville? ### How many days is enough for Gentryville? ### How to find the best Gentryville package deals? ### Is it cheaper to book a Gentryville vacation as a package? ### When to book a vacation package to Gentryville? ### Does Expedia offer Book Now, Pay Later Gentryville vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.