Rolling Hills Vacations from ￥77,368

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The Latest Rolling Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Juliette Hostel for Women Only

Juliette Hostel for Women Only

2 out of 5
San Juan Antiguo
per person
Oct 17 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to San Juan (SJU)
9.2/10 Wonderful! (61 reviews)
The staff here are very respectful kind and accommodating. I had no issues whatsoever I even made new friends with the ladies I roomed with. I most definitely recommend staying here.

Reviewed on Jul 21, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
per person
Oct 17 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to San Juan (SJU)
8.8/10 Excellent! (500 reviews)
Very pretty the property

Reviewed on Jul 20, 2025

Bali Posh Hotel PR

Bali Posh Hotel PR

2.5 out of 5
Isla Verde
per person
Oct 17 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to San Juan (SJU)
8.4/10 Very Good! (606 reviews)
Love the staff and service!! I recommend it 1000% and I will be coming back!! ☺️

Reviewed on Jul 23, 2025

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
Isla Verde
per person
Oct 17 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to San Juan (SJU)
8.4/10 Very Good! (1,795 reviews)
It was definitely easy to check in. It was clean the service was amazing. Definitely 10/10

Reviewed on Jul 20, 2025

La Calma Poshtel

La Calma Poshtel

2 out of 5
Santurce
per person
Oct 17 - Oct 21
found 9 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to San Juan (SJU)
7/10 Good! (484 reviews)
The Poshtel was very comfortable and overall very clean. The room info took a little longer to receive after payment which was a little inconvenient because there’s no lobby to the Poshtel so I was waiting on the street until i urgently asked for the info that should have been provided. The room was clean but there was issues with the towels they just didn’t smell or feel clean . Overall for the affordable price point the room was a life saver for my trip in Puerto Rico. If I return to the island I will be sure to book again just bring my own towels

Reviewed on Jul 9, 2025

Find the Best Rolling Hills Vacation Packages

Rolling Hills Hotel Deals

Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
6063 Isla Verde Avenue, Carolina
The price is ￥51,163 per night from Jul 27 to Jul 28
￥51,163
￥68,717 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,839 reviews)
"It was definitely easy to check in. It was clean the service was amazing. Definitely 10/10"

Reviewed on Jul 20, 2025

Fairmont El San Juan Hotel
Hyatt Regency Grand Reserve Puerto Rico

Hyatt Regency Grand Reserve Puerto Rico

4 out of 5
200 Coco Beach Blvd. Highway 955-I, Río Grande
Fully refundableReserve now, pay when you stay
The price is ￥30,375 per night from Aug 4 to Aug 5
￥30,375
￥39,070 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (2,371 reviews)
"The location was great and the people at the hotel did a great job making you field welcome."

Reviewed on Jul 20, 2025

Hyatt Regency Grand Reserve Puerto Rico
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort

5 out of 5
6000 Rio Mar Boulevard, Río Grande
The price is ￥51,163 per night from Jul 27 to Jul 28
￥51,163
￥69,286 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (2,081 reviews)
"Great"

Reviewed on Jul 21, 2025

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
See all 3,967 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.

Discover the most popular places to visit in Rolling Hills

Luquillo Beach featuring a beach

Luquillo Beach

Sample local street food or doze under a palm tree on this picturesque stretch of coast.

Luquillo Beach
Condado Beach featuring kayaking or canoeing, a sandy beach and tropical scenes

Condado Beach

This beach within the bustling city of San Juan is the perfect place to relax for a few hours.

Condado Beach

What to do in Rolling Hills

El Yunque Rainforest Natural Waterslide on a sunny Puerto Rico Day

El Yunque Waterslide and Waterfall Tour with Food and Photos

￥10,115
per adult
94% of travellers recommend
El Yunque Waterslide and Waterfall Tour with Food and Photos
Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

￥9,967
per adult
80% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
City Lights / GLOW

LED Kayak Night Glow Tour in Condado Lagoon

￥10,994
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
See all activities in Rolling Hills

Frequently asked questions

How much does a Rolling Hills vacation package cost?
You'll find cheap prices from ￥77,368 on Expedia for your Rolling Hills break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Rolling Hills costs.
What are the cheapest months to go to Rolling Hills?
September, October and November are great times to look for cheap Rolling Hills vacation packages. Choosing to travel in less busy periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Rolling Hills?
With a well-organized itinerary, you can easily hit the top Rolling Hills attractions in a few days. But if you prefer to discover lesser-known spots or go on day tours, consider booking your Rolling Hills vacation for longer.
How to find the best Rolling Hills package deals?
Use Expedia's handy filters to help you find some unbeatable Rolling Hills package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Rolling Hills package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Rolling Hills vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Rolling Hills vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Rolling Hills?
If you have your Rolling Hills vacation dates confirmed, book as soon as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Rolling Hills?

  1. Choose when to travel: Check your schedule and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to vacation in Rolling Hills.
  2. Set your budget: Factor in costs like flights, transportation and food when working out how much to set aside for your trip to Rolling Hills. Then, pick a property that suits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Rolling Hills. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels 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.