Rolling Hills Holidays

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Top hotels in Rolling Hills

Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street, San Juan
Fully refundableReserve now, pay when you stay
The price is €238 per night from 15 Sept to 16 Sept
€238
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very Good! (2,179 reviews)
"Safe , quiet , shopping , dining options was the best part"

Reviewed on 19 Aug 2025

Caribe Hilton
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 €229 per night from 8 Sept to 9 Sept
€229
8 Sept - 9 Sept
includes taxes & fees
8.8/10 Excellent! (2,522 reviews)
"Property was very clean and nice, pool was nice and warm. Great stay"

Reviewed on 21 Aug 2025

Hyatt Regency Grand Reserve Puerto Rico
Fairmont El San Juan Hotel

Fairmont El San Juan Hotel

5 out of 5
6063 Isla Verde Avenue, Carolina
Fully refundableReserve now, pay when you stay
The price is €334 per night from 1 Sept to 2 Sept
€334
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,917 reviews)
"The hotel is amazing. Staff super friendly. The cafe next to the lobby is really good . We had an amazing time . Hopefully coming back next year."

Reviewed on 22 Aug 2025

Fairmont El San Juan Hotel
See all 4,072 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.

Popular places to visit

Luquillo Beach showing a beach

Luquillo Beach

5/5(2 reviews)

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

Luquillo Beach
Condado Beach featuring a coastal town, kayaking or canoeing and a sandy beach

Condado Beach

4.5/5(3 reviews)

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

Condado Beach
Escambron Beach

Escambron Beach

4/5(1 review)

Swim in calm waters among colorful fish at a picturesque beach that is regularly voted one of the best in Puerto Rico.

Escambron Beach

What to do in Rolling Hills

Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

€59
per adult
74% of travellers recommend
Puerto Rico: UTV and Can-Am Sightseeing Tours
City Lights / GLOW

LED Kayak Night Glow Tour in Condado Lagoon

€65
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
San Juan: Casa Bacardi Distillery Tour

San Juan: Casa Bacardi Distillery Tour

€39
per adult
90% of travellers recommend
San Juan: Casa Bacardi Distillery Tour
See all activities in Rolling Hills

Frequently asked questions

How much does a Rolling Hills holiday package cost?
You'll find cheap prices 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 holiday 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 holiday 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-organised 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 holiday 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 holiday package well in advance.
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 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Rolling Hills?
If you have your Rolling Hills holiday 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 favourite time of year and the type of activities on offer will also help you decide when to holiday 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 customised Rolling Hills holiday package.

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