Greensburg Vacations from $421
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Your Greensburg Vacation
With a Greensburg vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your getaway has been taken care of before you depart, so you can spend more time discovering this lively city. Like some inspiration on what to see or do first during your trip to Greensburg? Head for major attractions like Skyline Drive-In Theatre. Your ultimate Greensburg vacation is a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored just for you.
The Latest Greensburg vacation packages
Price found within the past 48 hours. Click for updated prices.
Pillow and Paddock B&B
$710
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
10/10 Exceptional! (52 reviews)
Courteous staff and the room was outstanding. It was our second stay at the inn. Everything is first class. We highly recommend it.
Reviewed on Dec 22, 2025
Hyatt Regency Louisville
Downtown Louisville
$450
per person
Dec 19 - Dec 22
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Gorgeous atrium style hotel just steps away from convention center. Lots to do and see near hotel.
Reviewed on Oct 1, 2026
Stay near popular Greensburg attractions
Skyline Drive-In Theatre
9.0/10 (2 reviews)
This 1956 drive-in theater offers a nostalgic experience watching first-run films under the stars. Arrive early to claim a prime spot and enjoy classic concessions before the show begins.
Hobson Island
Commune with nature and explore the great outdoors at Hobson Island during your travels in Greensburg. Take in the theater scene while you're in the area.
Marcum Island
This secluded Kentucky island offers a tranquil escape surrounded by wetlands and natural beauty. Explore its serene landscape during spring when wildflowers enhance the peaceful walking experience.
Russell Island
Commune with nature and explore the great outdoors at Russell Island during your travels in Greensburg. Take in the theater scene while you're in the area.
White Island
Commune with nature and explore the great outdoors at White Island during your travels in Greensburg. Take in the theater scene while you're in the area.
Green County Public Library
This welcoming community hub offers diverse resources and comfortable reading areas for all ages. Explore their digital newspaper archives or join one of their regular educational programs.
Greensburg Hotel Deals
Walk to Dtwn Greensburg: Charming Unit w/ Deck!
Greensburg KY
10/10 Exceptional! (1 review)
Perfect
"What a great place in a perfect location. The beds were comfortable and we had everything we needed. We walked to restaurants and the Green River. We will definitely be back."
Reviewed on Jul 7, 2025
Modern Secluded Riverfront Cabin
Greensburg KY
$204 nightly
$219 total
Oct 12 - Oct 13
Total with taxes and fees
10/10 Exceptional! (17 reviews)
"Nice place. Host was very organized and had great communication."
Reviewed on Aug 31, 2026
Baymont by Wyndham Cave City
799 Mammoth Cave St Cave City KY
Fully refundableReserve now, pay when you stay
$57 nightly
$63 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"We enjoyed our overnight stay. The property is well maintained and a great location for visiting Mammoth Cave."
Reviewed on Oct 3, 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 Greensburg Vacation Packages
Greensburg Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,100 |
Max Temp Winter | 45ºF |
Max Temp Summer | 85ºF |
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Frequently asked questions
How much does a Greensburg vacation package cost?
You can grab a vacation package to this popular destination from $421 on Expedia. But how much your vacation to Greensburg costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Greensburg?
November, December and January are the best times to search for cheap Greensburg vacation packages. Choosing to travel in quieter periods means you can generally find lower prices on flights and hotels.
How many days is enough for Greensburg?
Usually, a handful of days is enough to tick off the top attractions during your Greensburg vacation. However, if you prefer to have time to kick back or go on day trips, think about extending your itinerary.
How to find the best Greensburg package deals?
Use Expedia's filter tool to help you find some tempting Greensburg package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Greensburg package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Greensburg vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can personalize your Greensburg escape to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Greensburg?
Land incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Greensburg break.
Does Expedia offer Book Now, Pay Later Greensburg vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Greensburg break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
