Rolling Hills Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Top Rolling Hills Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sage & Sand Motel

Sage & Sand Motel

2.5 out of 5
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Casper (CPR)
7.8/10 Good! (46 reviews)
Good location for one night sleep

Reviewed on Jul. 17, 2025

Riverside Hotel

Riverside Hotel

2.5 out of 5
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Casper (CPR)
8/10 Very Good! (534 reviews)
Very nice and newly remodeled!

Reviewed on Jul. 25, 2025

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Rolling Hills Hotel Deals

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 Jun. 22, 2025

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

Pony Express Silverleaf Retreat

Glenrock
The price is CA $160 per night from Jul 29 to Jul 30
CA $160
CA $210 total
Jul 29 - Jul 30
includes taxes & fees
10/10 Exceptional! (1 review)
Wonderful retreat with great views
"Beautiful property with views of chickens, deer and great views of the hill side. Totally relaxing space and front deck. This place is pristine."

Reviewed on Jun. 28, 2025

Pony Express Silverleaf Retreat
Deer Creek Pony Express Cabin

Deer Creek Pony Express Cabin

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

Reviewed on Jul. 23, 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Rolling Hills vacation package cost?
Offering great value package deals from CA $1,256 on Expedia, you'll be thrilled with how little a vacation to Rolling Hills costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Rolling Hills?
You can usually find reduced prices and greater availability in January, February and April. Explore our cheap Rolling Hills vacation packages and you could get some excellent off-season deals.
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 prefer to venture off the beaten track or go on day trips, think about booking your Rolling Hills vacation for longer.
How to find the best Rolling Hills package deals?
Start your search for a Rolling Hills package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Rolling Hills package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Rolling Hills escape off to a flying start.
Is it cheaper to book a Rolling Hills vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component separately. And you'll still have the flexibility to create a customized Rolling Hills vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Rolling Hills?
If you're considering a spontaneous Rolling Hills getaway, 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 score awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Rolling Hills?

  1. Choose your dates: What you plan to do in Rolling Hills and your preferred season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your hotel will probably be the biggest expense during your trip to Rolling Hills.
  3. Decide how long to go for: Now that you're up to speed on Rolling Hills, you can figure out the right length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized 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.