Greensburg Vacations from $619

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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.
Marriott Louisville East

Marriott Louisville East

4 out of 5
Jeffersontown
Price was $731, price is now $619 per person
$619
per person
Aug 1 - Aug 5
found 4 hours ago
Roundtrip non-stop flight included
New York (JFK) to Louisville (SDF)
9/10 Wonderful! (1,004 reviews)
We were treated to some excellent live bluegrass music at the bar.

Reviewed on Jun 5, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $793, price is now $657 per person
$657
per person
Jul 27 - Jul 30
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Louisville (SDF)
8.8/10 Excellent! (1,003 reviews)
Beautiful place i want to stay

Reviewed on May 31, 2026

The Trail Hotel

The Trail Hotel

4 out of 5
Price was $1,046, price is now $867 per person
$867
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Louisville (SDF)
9/10 Wonderful! (199 reviews)
Fun environment with convenience of a restaurant and loved the pool!

Reviewed on Jun 3, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was $918, price is now $762 per person
$762
per person
Jul 27 - Jul 30
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Louisville (SDF)
9/10 Wonderful! (1,002 reviews)
Excellent customer service. Centrally located.

Reviewed on Jun 1, 2026

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
Price was $886, price is now $758 per person
$758
per person
Jul 27 - Jul 30
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Louisville (SDF)
9.4/10 Exceptional! (1,229 reviews)
Loved the beautiful historic architecture. Had my first Hot Brown & loved it. Sunset on the 16 th floor was spectacular.

Reviewed on Jun 6, 2026

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Discover the most popular places to visit in Greensburg

Skyline Drive-In Theatre

You can get tickets for a performance at Skyline Drive-In Theatre on your trip to Greensburg. While you're in the area, stroll along the marina.

Skyline Drive-In Theatre

Greensburg Hotel Deals

The House at Cedar Grove

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

Get rates
The House at Cedar Grove
Charming Vintage Home

Charming Vintage Home

Greensburg KY
$191 nightly
The price is $204 total per night from Jun 8 to Jun 9
$204 total
Jun 8 - Jun 9
Total with taxes and fees
9.6/10 Exceptional! (34 reviews)
"The house was very clean, plenty of towels and wash cloths. It worked great for our family of six."

Reviewed on Feb 9, 2026

Charming Vintage Home
Red Roof Inn & Suites Cave City

Red Roof Inn & Suites Cave City

2 out of 5
807 Mammoth Cave St Cave City KY
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Jul 1 to Jul 2
$66 total
Jul 1 - Jul 2
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
"Air / heat unit made more noise than most, beds a little firmer than we're used to. Coffee only in the morning."

Reviewed on Jun 7, 2026

Red Roof Inn & Suites Cave City
See all 197 properties in Greensburg
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 $619 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.