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 $1,156, price is now CA $977 per person
CA $977
per person
Jan 27 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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 $1,581, price is now CA $1,239 per person
CA $1,239
per person
Jan 27 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.8/10 Excellent! (1,004 reviews)
Housekeeping knocked

Reviewed on Nov 8, 2026

Hotel Distil, Autograph Collection

Hotel Distil, Autograph Collection

4 out of 5
Downtown Louisville
Price was CA $1,910, price is now CA $1,586 per person
CA $1,586
per person
Jan 27 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
9.6/10 Exceptional! (511 reviews)
Excellent location and room!

Reviewed on Nov 6, 2026

The Grady

The Grady

4 out of 5
Downtown Louisville
Price was CA $1,429, price is now CA $1,219 per person
CA $1,219
per person
Jan 27 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
9.4/10 Exceptional! (1,003 reviews)
Would definitely stay here again.

Reviewed on Nov 8, 2026

Holiday Inn Express Louisville Airport Expo Center by IHG

Holiday Inn Express Louisville Airport Expo Center by IHG

2.5 out of 5
Hayfield Dundee
Price was CA $1,141, price is now CA $986 per person
CA $986
per person
Jan 27 - Jan 31
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Louisville (SDF)
8.6/10 Excellent! (1,005 reviews)
Check in was great and fast.The room was nice and clean.The breakfast was above average.Also my daughter flew in from Houston and the staff picked her up with the shuttle from the airport with no problem

Reviewed on Nov 8, 2026

Ready to book your vacation to Rolling Hills?

 

Choose your dates

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 $192 per night from Nov 22 to Nov 23
CA $192
CA $226 total
Nov 22 - Nov 23
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 $147 per night from Nov 25 to Nov 26
CA $147
CA $173 total
Nov 25 - Nov 26
includes taxes & fees
9.4/10 Exceptional! (1,467 reviews)
"The breakfast was lively. The building beautiful. Lovely big room"

Reviewed on Nov 8, 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 $131 per night from Nov 17 to Nov 18
CA $131
CA $154 total
Nov 17 - Nov 18
includes taxes & fees
9.6/10 Exceptional! (2,620 reviews)
"Excelente todo. Solo el desayuno no es la gran cosa para si le dan la opción de pedir desayuno no lo compren no vale la pena en lo demás recomiendo el lugar mil veces"

Reviewed on Nov 8, 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.
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All Inclusive Vacations
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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 $977 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.