Rolling Hills Vacations from $619

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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.
Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was $696, price is now $619 per person
$619
per person
Dec 22 - Dec 24
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Bed was hard but good stay

Reviewed on Nov 14, 2026

Omni Louisville Hotel

Omni Louisville Hotel

4 out of 5
Downtown Louisville
Price was $799, price is now $689 per person
$689
per person
Feb 2 - Feb 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.4/10 Exceptional! (2,202 reviews)

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was $770, price is now $674 per person
$674
per person
Feb 2 - Feb 4
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Louisville (SDF)
9.6/10 Exceptional! (511 reviews)
Very luxurious hotel in a great location for great restaurants and some shopping. Close to some Louisville attractions like the Slugger museum, Angel’s Envy and Old Forester distilleries. The Repeal restaurant inside the hotel was truly a perfect experience!

Reviewed on Nov 10, 2026

Homewood Suites by Hilton Louisville Downtown, KY

Homewood Suites by Hilton Louisville Downtown, KY

3 out of 5
Downtown Louisville
Price was $1,172, price is now $1,033 per person
$1,033
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
9.4/10 Exceptional! (1,009 reviews)
This was one of the best moderate price hotels in which we’ve ever stayed. The hotel was beautifully decorated; room was spacious and comfortable; staff were great and breakfast was exceptional with a huge variety with lots of toppings and touches. Location was perfect as well for our downtown walking exploration.

Reviewed on Nov 13, 2026

Wingate by Wyndham Louisville East

Wingate by Wyndham Louisville East

3 out of 5
Jeffersontown
Price was $987, price is now $877 per person
$877
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Denver (DEN) to Louisville (SDF)
8.6/10 Excellent! (1,007 reviews)
Not impressed with this place at all, walk in all lighting is dim and depressing, room is worn and furniture with soils. Breakfast buffet was a joke and was supposed to be the best around. Front desk people rarely at the counter that is also in a dark corner like they don’t want you to see them. Room service: asked them to service the room, new towels were replaced but no toilet paper and they didn’t bother to vacuum. Plumbing in the shower a mess, toilet you have to hold down for it to flush. Unacceptable hotel

Reviewed on Nov 14, 2026

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What to do in Rolling Hills

Kentucky Derby Museum

Kentucky Derby Museum - General Admission and Guided Track Visit

$24
per adult
94% of travellers recommend
Kentucky Derby Museum - General Admission and Guided Track Visit
Louisville: 3-Hour Food and History Tour of NuLu District

Louisville: 3-Hour Food and History Tour of NuLu District

$129
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby

$29
per adult
92% of travellers recommend
Old Louisville Ghost Tour as Recommended by The New York Times @ 4th and Ormsby
See all activities in Rolling Hills

Rolling Hills Hotel Deals

Galt House Hotel Trademark Collection by Wyndham

Galt House Hotel Trademark Collection by Wyndham

4 out of 5
140 North Fourth Street Louisville KY
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $152 total per night from Nov 24 to Nov 25
$152 total
Nov 24 - Nov 25
Total with taxes and fees
9/10 Wonderful! (4,511 reviews)
"clean room"

Reviewed on Nov 14, 2026

Galt House Hotel Trademark Collection by Wyndham
The Brown Hotel

The Brown Hotel

4.5 out of 5
335 W Broadway Louisville KY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $143 total per night from Nov 22 to Nov 23
$143 total
Nov 22 - Nov 23
Total with taxes and fees
9.4/10 Exceptional! (1,482 reviews)
"Great hotel. Historic and well maintained. Food and service at the bar is the best of anywhere you can go."

Reviewed on Nov 14, 2026

The Brown Hotel
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)

4 out of 5
4520 Poplar Level Rd Louisville KY
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $108 total per night from Nov 17 to Nov 18
$108 total
Nov 17 - Nov 18
Total with taxes and fees
9.6/10 Exceptional! (2,623 reviews)
"Ok"

Reviewed on Nov 14, 2026

Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,162 properties in Rolling Hills
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

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Frequently asked questions

How much does a Rolling Hills vacation package cost?
You'll find cheap prices from $619 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.