Rolling Hills Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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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.
Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Louisville (SDF)
9/10 Wonderful! (630 reviews)
Cool property, good restaurant and solid location!

Reviewed on Jun. 14, 2025

Caesars Southern Indiana

Caesars Southern Indiana

3.5 out of 5
per person
Sep 19 - Sep 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.2/10 Very Good! (1,002 reviews)
Pool closed I am told for “months” unacceptable I needed to warm som food for my grandma, told at desk, “no microwave available “ on entire property, $30 for breakfast? Really???

Reviewed on Jul. 13, 2025

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
per person
Sep 19 - Sep 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8.8/10 Excellent! (1,003 reviews)
Staff was incredible. Room was okay, but not excellent, as the bathroom was not well-cleaned or ventilated.

Reviewed on Jun. 26, 2025

Hancock House

Hancock House

3 out of 5
Downtown Louisville
per person
Sep 19 - Sep 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
8/10 Very Good! (236 reviews)
Excellent location, great parking, well equipped apartment with a comfortable bed. I’d highly recommend to anyone wanting to explore Louisville, and will definitely stay again!

Reviewed on Jul. 3, 2025

The Brown Hotel

The Brown Hotel

4.5 out of 5
Downtown Louisville
per person
Sep 19 - Sep 21
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Louisville (SDF)
9.4/10 Exceptional! (1,018 reviews)
For been an old property, is in good condition, staff is friendly and helpful.

Reviewed on Jul. 13, 2025

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 $193 per night from Aug 10 to Aug 11
CA $193
CA $228 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (3,445 reviews)
"Downtown location. Beautiful room!"

Reviewed on Jul. 12, 2025

Galt House Hotel Trademark Collection by Wyndham
Crowne Plaza Louisville Airport Expo Ctr by IHG
Crowne Plaza Louisville Airport Expo Ctr by IHG
3.5 out of 5
830 Phillips Lane, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 21 to Jul 22
CA $129
CA $152 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (643 reviews)
"Comfortable"

Reviewed on Jul. 11, 2025

Crowne Plaza Louisville Airport Expo Ctr by IHG
Omni Louisville Hotel
Omni Louisville Hotel
4 out of 5
400 S. 2nd Street, Louisville, KY
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Aug 8 to Aug 9
CA $218
CA $256 total
Aug 8 - Aug 9
includes taxes & fees
9.2/10 Wonderful! (1,502 reviews)
"beautiful hotel. great location"

Reviewed on Jul. 10, 2025

Omni Louisville Hotel
See all 2,025 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

Discover the most popular places to visit in Rolling Hills

Kentucky Exposition Center

Kentucky Exposition Center

4.5/5(14 reviews)

Learn about the events happening at Kentucky Exposition Center during your trip to Louisville. Experience the area's lively festivals and great live music.

Kentucky Exposition Center
Churchill Downs showing land animals and horse riding as well as a small group of people

Churchill Downs

4.5/5(22 reviews)

Find more than mint juleps to enjoy at this iconic racetrack, best known as the annual host of the Kentucky Derby.

Churchill Downs
Louisville Slugger Museum featuring interior views

Louisville Slugger Museum

4.5/5(18 reviews)

Baseball is part of the American fabric. See where one important tool for this sport is produced in the factory that makes ball games possible.

Louisville Slugger Museum

What to do in Rolling Hills

Derby City Ghosts: Louisville Hauntings Tour

Derby City Ghosts: Louisville Hauntings Tour

CA $44
per adult
Derby City Ghosts: Louisville Hauntings Tour
Where every day is Derby Day!

Kentucky Derby Museum General Admission Ticket

CA $30
per adult
90% of travellers recommend
Kentucky Derby Museum General Admission Ticket
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

Self Guided Driving Tour to Four Kentucky Bourbon Distilleries

CA $41
per traveller
Self Guided Driving Tour to Four Kentucky Bourbon Distilleries
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 $719 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.