Rolling Hills Vacation Packages

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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.

Top Rolling Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,078, price is now CA $885 per person
CA $885
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
8.8/10 Excellent! (1,012 reviews)

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,350, price is now CA $1,139 per person
CA $1,139
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
There was no room available for my accommodation after I drove 6 hours and notifies the hotel of my arrival time. When I got to the registration desk I was notified that the hotel was full and I needed to stay at an hotel that was substandard to the Hyatt. I was then directed to a holiday inn that was 15 minutes away from downtown which made my business trip meeting difficult considering all my colleagues were staying downtown.

Reviewed on Oct 24, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,697, price is now CA $1,434 per person
CA $1,434
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.6/10 Exceptional! (511 reviews)

Holiday Inn Louisville Airport South by IHG

Holiday Inn Louisville Airport South by IHG

3 out of 5
Price was CA $1,084, price is now CA $932 per person
CA $932
per person
Jan 6 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was CA $1,580, price is now CA $1,373 per person
CA $1,373
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Louisville (SDF)
9.4/10 Exceptional! (1,003 reviews)

Ready to book your vacation to Rolling Hills?

 

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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
The price is CA $190 per night from Nov 9 to Nov 10
CA $190
CA $224 total
Nov 9 - Nov 10
includes taxes & fees
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
The price is CA $146 per night from Nov 25 to Nov 26
CA $146
CA $172 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,446 reviews)
"Wonderful stay at the Brown Hotel. Beautiful hotel with top notch service. Had a concern with our room and Management was quick to respond and moved us to an upgraded room. Customer service is unmatched. Kind and helpful staff. The food is amazing in the cafe and the restaurant. Upscale old school ..."

Reviewed on Oct 30, 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
The price is CA $125 per night from Nov 3 to Nov 4
CA $125
CA $147 total
Nov 3 - Nov 4
includes taxes & fees
Derby City Gaming & Hotel - A Churchill Downs Property (Adults Only)
See all 2,144 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Rolling Hills

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

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

CA $182
per adult
94% of travellers recommend
Louisville: 3-Hour Food and History Tour of NuLu District
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket

CA $28
per adult
94% of travellers recommend
Louisville: Muhammad Ali Center Skip-the-Line Entry Ticket
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour

CA $14
per adult
80% of travellers recommend
Old Louisvilles Famous Ghosts Smartphone Guided Walking Tour
See all activities in Rolling Hills

Frequently asked questions

How much does a Rolling Hills vacation package cost?
You'll find cheap prices from CA $885 on Expedia for your Rolling Hills escape. However, a range of factors like the length of stay, the season 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?
You can typically find lower prices and greater availability in January, February and November. Take a look at our cheap Rolling Hills vacation packages and you could land some great off-season deals.
How many days is enough for Rolling Hills?
Rolling Hills vacations can be short or long, but to get a real feel for this place, we'd say 2 days is about right. This will mean you can visit top sights like Oxmoor Centre and Paddock Shops and track down some lesser-known spots. Don't forget to visit neighbourhoods such as Hurstbourne and Lyndon either. If you're clever with your time, you can even take a day trip outside of Rolling Hills too.
How to find the best Rolling Hills package deals?
Begin your search for a Rolling Hills package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Rolling Hills package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Rolling Hills adventure underway.
Is it cheaper to book a Rolling Hills vacation as a package?
You can enjoy significant savings on your Rolling Hills getaway by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Rolling Hills?
If you're considering a spontaneous Rolling Hills adventure, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Rolling Hills?

  1. Pick your travel dates: The things you'd like to do in Rolling Hills and your favourite season can help you decide when to get away.
  2. Set your budget: Factor in costs such as food, flights and transportation when calculating how much to put aside for your trip to Rolling Hills. Then, pick a property that fits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Decide how long to go for: Now that you're more familiar with Rolling Hills, you can figure out the perfect length of your vacation. Put together a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Rolling Hills vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.