Rolling Hills Vacations from $377

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Your Rolling Hills Vacation

Say farewell to the worries of planning and hello to a Rolling Hills vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Jaguas, which is great for nature, watersports and hiking. Fill your schedule with tours of Jose Miguel Agrelot Coliseum, Carolina Beach and Isla Verde Beach, some of the top attractions you just have to see during your trip to Rolling Hills. Don't put off your visit to this city any longer. Your dream Rolling Hills vacation is a couple of clicks away with Expedia.

The Latest Rolling Hills vacation packages

Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel

Ola Boutique Hotel

4.5 out of 5
Condado
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (453 reviews)
Place was very nice to us felt like home

Reviewed on Aug 12, 2025

Urbana Hotel

Urbana Hotel

2 out of 5
San Juan Antiguo
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (317 reviews)
Is there any way i can get a refund since i checked out a day earlier

Reviewed on Aug 16, 2025

The Oliver Hotel

The Oliver Hotel

3 out of 5
San Juan Antiguo
Save 100% on your flight
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (32 reviews)
El hotel por dentro es muy bonito, el staff amable. Pero, como es nuevo necesitan estar mas al día con el mantenimiento (aires, inodoros, agua caliente, etc). También mejorar el manejo de los empleados de limpieza (debe hacer menos escándalo) y mejorar la comunicación con las personas de mantenimiento (horarios para hacerlo y si hay huéspedes en la habitación o no).

Reviewed on Aug 9, 2025

San Agustin Apartments

San Agustin Apartments

3 out of 5
San Juan Antiguo
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (370 reviews)
Worked with me on short notice! Nice property! Great communication! Amazing hosts!

Reviewed on Aug 16, 2025

VILLA JOYUDA

VILLA JOYUDA

3 out of 5
Save 100% on your flight
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
No reviews
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Discover the most popular places to visit in Rolling Hills

San Juan Antiguo showing general coastal views and a coastal town

Port of San Juan

4.5/5(2,281 reviews)

Explore the waterfront in San Juan with a trip to Port of San Juan. Discover the area's top-notch restaurants and its acclaimed art scene.

Port of San Juan
Luquillo Beach featuring a beach

Luquillo Beach

4.5/5(1,031 reviews)

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

4.5/5(1,500 reviews)

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

Puerto Rico: UTV and Can-Am Sightseeing Tours

Puerto Rico: UTV and Can-Am Sightseeing Tours

$68
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

$75
per adult
92% of travellers recommend
LED Kayak Night Glow Tour in Condado Lagoon
Bioluminescent Bay Night Kayaking Experience in Fajardo

Bioluminescent Bay Night Kayak Experience in Fajardo (transport optional)

$49
per adult
88% of travellers recommend
Bioluminescent Bay Night Kayak Experience in Fajardo (transport optional)
See all activities in Rolling Hills

Rolling Hills Hotel Deals

Caribe Hilton

Caribe Hilton

4.5 out of 5
1 San Geronimo Street, San Juan
Fully refundableReserve now, pay when you stay
$254 nightly
The price is $277 total per night from Sep 15 to Sep 16
$277 total
Sep 15 - Sep 16
Total includes taxes and fees
8.4/10 Very Good! (2,153 reviews)
"We liked the room, we had a nice ocean view. The maid came daily which was nice. We liked the free bottles of water from concierge desk. We could walk to the nice beach about a 6 minute walk. Hotel beach was closed due to excessive seaweed. Pools were nice. Hot tubs very small and not hot. Strong ..."

Reviewed on Aug 17, 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
$306 nightly
The price is $333 total per night from Aug 18 to Aug 19
$333 total
Aug 18 - Aug 19
Total includes taxes and fees
8.8/10 Excellent! (2,481 reviews)
"The room was amazing, clean and beautiful. Restaurants were so good. Valet parking service is horrible. Servers at restaurants are professional and nice"

Reviewed on Aug 16, 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
$422 nightly
The price is $469 total per night from Aug 18 to Aug 19
$469 total
Aug 18 - Aug 19
Total includes taxes and fees
8.4/10 Very Good! (1,907 reviews)
"If you need a place to relax, I would definitely recommend. We enjoyed our time there, and the staff is amazing"

Reviewed on Aug 15, 2025

Fairmont El San Juan Hotel
See all 4,009 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.

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Frequently asked questions

How much does a Rolling Hills vacation package cost?
You'll find cheap prices from $377 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?
You're likely to find lower rates and better availability in September, October and December. Explore our cheap Rolling Hills vacation packages and you could score some great off-season deals.
How many days is enough for Rolling Hills?
With a well-organized travel plan, you can easily hit the top Rolling Hills sights in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about 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.
Does Expedia offer Book Now, Pay Later Rolling Hills vacation packages?
Jet off on your ideal getaway to Rolling Hills with Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.