Greensburg Vacations from $722
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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.
Holiday Inn Express Louisville Airport Expo Center by IHG
Hayfield Dundee
$722
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
8.6/10 Excellent! (1,010 reviews)
It is absolutely misleading seeing the 8.6 rating for this property! Location is 100 % unsafe! I’m 6’6” 250 lbs and I felt uneasy walking the parking lot at 10:30pm. There was a homeless guy half naked sitting in front of the entrance yelling obscenities as we walked in. Inside looked and smelled as decommissioned mental institution against better judgment checked in and went to the room. In the room it got even worse smell was horrible the beds were made but it looked like someone sat on them bathroom was grimy and smelled even worse than the room it was dark it was noisy (room 319 directly overlooks the interstate). I checked out 10 mins later cause for same price you can ….
Reviewed on Aug 19, 2026
Louisville Marriott Downtown
Downtown Louisville
$1,224
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Property was nice! Room was as expected! Valet/service was much to be desired! Room service snd bar service was some of the worst I’ve ever encountered! Was told by room service they had water; but if I wanted then I had to come get them myself! She wasn’t delivering them! Bartender in the hotel lounge was so bad it was laughable!! Told us she was doing us a favor by waiting on us! Lost her mind when I ask for 3 small bowls to put nuts in so our party of eight didn’t have to pass around the same cardboard cup she put them in!
Reviewed on Aug 16, 2026
Hotel Distil, Autograph Collection
Downtown Louisville
$1,227
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (489 reviews)
Love this hotel. The bed was incredibly comfortable for a hotel bed. Linens were high end. Staff were great - neighborhood was great. Restaurant had a great breakfast. Would definitely stay again.
Reviewed on Aug 5, 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.
Greensburg City Hall
Greensburg City Hall houses the mayor's office and city administration in this Kentucky town. Visit during regular weekday hours or attend a public council meeting on the third Monday of each month.
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.
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.
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.
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.
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.
Greensburg Hotel Deals
The House at Cedar Grove
Greensburg KY
10/10 Exceptional! (18 reviews)
Ashley’s Wedding Party
"We had such a wonderful experience at this amazing home. This home was the perfect size for our family to gather and prepare for a family wedding. We has so much space, fun with the pool table, movie theater, and ping pong table. It was spotless, efficient and the owners were so quick and friendly ..."
Reviewed on Jun 2, 2025
Red Roof Inn & Suites Cave City
807 Mammoth Cave St Cave City KY
Fully refundableReserve now, pay when you stay
$58 nightly
$65 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (1,010 reviews)
"Good value and cleanliness for the price"
Reviewed on Aug 18, 2026
Baymont by Wyndham Cave City
799 Mammoth Cave St Cave City KY
Fully refundableReserve now, pay when you stay
$65 nightly
$72 total
Sep 1 - Sep 2
Total with taxes and fees
8/10 Very Good! (1,027 reviews)
"It's a cheap place to sleep for a couple of nights, no more. Rooms were decent. Pool was dirty, so we did not want to go in. Property grounds were clean. Internet was good enough. Parking was free and easy. Lots of Fast Food and a few restaurants in the same block. We had 2 rooms next to each other. ..."
Reviewed on Aug 19, 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 $722 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.
