Rolling Hills Holidays

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    Better together

    Save up to €185 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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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Rolling Hills

Little R&R, Entire Farmhouse, Historical 1908 Train Station

Little R&R, Entire Farmhouse, Historical 1908 Train Station

Evansville
9.8/10 Exceptional! (14 reviews)
Family trip
"Wonderful stay and location."

Reviewed on 22 Jun 2025

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Little R&R, Entire Farmhouse, Historical 1908 Train Station
Pony Express Silverleaf Retreat

Pony Express Silverleaf Retreat

Glenrock
10/10 Exceptional! (2 reviews)
"Really clean with a beautiful view off the front porch. Fenced in back yard with plenty of shade. Deer and turkeys afoot. Loved the openness of the living room kitchen area. Got dinner to go from a local restaurant and ate on the front deck as the sun was going down. 12/10. Would definitely stay ..."

Reviewed on 26 Jul 2025

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Pony Express Silverleaf Retreat
Deer Creek Pony Express Cabin

Deer Creek Pony Express Cabin

Glenrock
10/10 Exceptional! (14 reviews)
"Very peaceful"

Reviewed on 23 Jul 2025

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Deer Creek Pony Express Cabin
See all 5 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.

Frequently asked questions

How much does a Rolling Hills holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Rolling Hills costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Rolling Hills?
January, February and April are the best times to search for cheap Rolling Hills holiday packages. Travelling in less busy periods means you can usually find reduced prices on accommodation and flights.
How many days is enough for Rolling Hills?
With a well-planned itinerary, you can easily tick off the top Rolling Hills attractions in a handful of days. But if you'd like to explore off the beaten track or take day trips, think about booking your Rolling Hills holiday for longer.
How to find the best Rolling Hills package deals?
Use Expedia's handy filters to help you find some tempting Rolling Hills package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Rolling Hills package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Rolling Hills holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the flexibility to create a customised Rolling Hills holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Rolling Hills?
If you're planning an impromptu Rolling Hills adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Rolling Hills?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Rolling Hills.
  2. Plan your budget wisely: Besides the price of your stay, you should consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could arise during your trip to Rolling Hills.
  3. Set the duration of your trip: Start by compiling a list of the attractions you'd like to get to in Rolling Hills. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodation and airfare: Once you've settled on your dates and duration, lock in the perfect Rolling Hills holiday package for you.

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