Rolling Hills Vacations from $774
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Rolling Hills Vacation
Reserve a Rolling Hills vacation package that includes everything you need and no unnecessary extras. Good for nightlife, distilleries and craft breweries and shopping, think about basing yourself in the neighborhood of East Market District. Make your trip to Rolling Hills even more enjoyable by going sightseeing. E.P. Tom Sawyer State Park, Mall St. Matthews and Springhurst Towne Center Shopping Center are among the top attractions you'll want to explore. No matter your travel plans or budget, putting together a tailored Rolling Hills vacation is a walk in the park with Expedia.
The Latest Rolling Hills vacation packages
Price found within the past 48 hours. Click for updated prices.
Pillow and Paddock B&B
$1,215
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Don't see what you're looking for?
See all available trips from Columbus to Rolling Hills
View all tripsWhat to do in Rolling Hills
Kentucky Derby Museum - General Admission and Guided Track Visit
$24
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
$129
per adult
94% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
$29
per adult
92% of travellers recommend
Rolling Hills Hotel Deals
Galt House Hotel Trademark Collection by Wyndham
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$144 nightly
$170 total
Oct 27 - Oct 28
Total with taxes and fees
The Brown Hotel
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$156 nightly
$183 total
Oct 25 - Oct 26
Total with taxes and fees
9.4/10 Exceptional! (1,370 reviews)
"A few tech upgrades in the room would have been nice, i.e. updated charging station."
Reviewed on Oct 12, 2026
Radisson Hotel Louisville North
505 Marriott Drive Clarksville IN
Fully refundable
$76 nightly
$85 total
Oct 19 - Oct 20
Total with taxes and fees
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 Rolling Hills Vacation Packages
Rolling Hills Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Louisville Intl. Airport (SDF) |
Population | 960 |
Top Sights | Kentucky Kingdom, Louisville Slugger Museum and Louisville Zoo |
More vacations you might like
Frequently asked questions
How much does a Rolling Hills vacation package cost?
You'll find cheap prices from $774 on Expedia for your Rolling Hills getaway. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Rolling Hills costs.
What are the cheapest months to go to Rolling Hills?
September, November and December are great times to look for cheap Rolling Hills vacation packages. Choosing to travel in less busy periods means you can generally find reduced prices on flights and hotels.
How many days is enough for Rolling Hills?
With a well-planned itinerary, you can easily hit the top Rolling Hills sights in a handful of days. But if you want to discover lesser-known spots or go on day trips, think about booking your Rolling Hills vacation for longer.
How to find the best Rolling Hills package deals?
Begin your search for a Rolling Hills package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Rolling Hills package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Rolling Hills adventure off to a flying start.
Is it cheaper to book a Rolling Hills vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Rolling Hills vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Rolling Hills?
Secure incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Rolling Hills getaway.
Does Expedia offer Book Now, Pay Later Rolling Hills vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Rolling Hills trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
