Chupacallos Vacations from $489

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Your Chupacallos Vacation

Reserve a Chupacallos vacation package that includes everything you need and no unnecessary extras. Good for bars and pubs, shopping and dining, consider staying in the neighborhood of Barrio Pueblo. If your trip to Chupacallos includes some sightseeing, drop by major attractions such as Playa Blanca, Playa Los Machos and Splash Tattoo. Expedia will help you escape your daily routine. Tailor your vacation to Chupacallos to suit your style of travel, whatever that may be.

The Latest Chupacallos vacation packages

Price found within the past 48 hours. Click for updated prices.
Lazy Parrot Inn

Lazy Parrot Inn

3 out of 5
Save 100% on your flight
Price was $875, price is now $489 per person
$489
per person
May 11 - May 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9.2/10 Wonderful! (1,000 reviews)
Great hotel, lots to do around.

Reviewed on Mar 3, 2026

Isla Verde Beachfront Retreat With Parking

Isla Verde Beachfront Retreat With Parking

2 out of 5
Isla Verde
Price was $1,456, price is now $818 per person
$818
per person
May 6 - May 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Juan (SJU)
No reviews
Fortaleza Suites

Fortaleza Suites

3.5 out of 5
Old San Juan
Price was $1,185, price is now $681 per person
$681
per person
May 7 - May 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (1,244 reviews)
Great location for old San juan

Reviewed on Mar 2, 2026

Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Higuillar
Save 100% on your flight
Price was $2,860, price is now $1,687 per person
$1,687
per person
Apr 10 - Apr 15
found 3 hours ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
10/10 Exceptional! (1 review)
Clean, great location, very freidly people

Reviewed on Feb 4, 2026

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
Price was $1,191, price is now $703 per person
$703
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (328 reviews)
Daily maid service, entire resort was near and tidy, restaurant and beach-side staff were super attentive. Entire resort is ****

Reviewed on Mar 2, 2026

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Discover the most popular places to visit in Chupacallos

Ceiba Ferry Terminal

3.5/5(109 reviews)

Explore the waterfront in Machos with a trip to Ceiba Ferry Terminal.

Ceiba Ferry Terminal

Splash Tattoo

Take the family on an outing to Splash Tattoo during your trip to Machos. Stroll along the area's seaside, or simply savor its top-notch restaurants.

Splash Tattoo

What to do in Chupacallos

Culebra Day Trip by Catamaran

Culebra Day Trip from Fajardo by Catamaran

$162
per adult
92% of travellers recommend
Culebra Day Trip from Fajardo by Catamaran
El Yunque Rainforest: Waterslides, Waterfalls and Rope Swing

El Yunque Rainforest: Waterslides, Waterfalls and Rope Swing

$25
per adult
84% of travellers recommend
El Yunque Rainforest: Waterslides, Waterfalls and Rope Swing
El Yunque Rainforest Guided Hiking with Waterfall Tour

El Yunque Rainforest Guided Hiking Tour

$88
per traveler
96% of travellers recommend
El Yunque Rainforest Guided Hiking Tour
See all activities in Chupacallos

Chupacallos Hotel Deals

El Conquistador Resort

El Conquistador Resort

4 out of 5
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
$434 nightly
The price is $473 total per night from Mar 8 to Mar 9
$473 total
Mar 8 - Mar 9
Total with taxes and fees
9/10 Wonderful! (3,250 reviews)
Amazing staff and property. Loved everything

Reviewed on Mar 3, 2026

El Conquistador Resort
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
$510 nightly
The price is $556 total per night from Mar 17 to Mar 18
$556 total
Mar 17 - Mar 18
Total with taxes and fees
9/10 Wonderful! (2,943 reviews)
Gorgeous!

Reviewed on Feb 28, 2026

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
$670 nightly
The price is $743 total per night from Mar 15 to Mar 16
$743 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (2,225 reviews)
The amenities were superb, the room was clean, and the staff were very attentive.

Reviewed on Mar 2, 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
See all 2,027 properties in Chupacallos
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.

Find the Best Chupacallos Vacation Packages

Chupacallos Essential Information

Language
Spanish
Currency
U.S dollars
Local Welcome
¡Hola!
Local Goodbye
Adiós
Closest Airport
Luis Munoz Marin Intl. Airport (SJU)
Top Sights
Playa Blanca, Playa Los Machos and Playa Medio Mundo

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Frequently asked questions

How much does a Chupacallos vacation package cost?
Offering great value package deals from $489 on Expedia, you'll be surprised at how little a vacation to Chupacallos costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Chupacallos?
You can generally find lower rates and greater availability in September, October and December. Explore our cheap Chupacallos vacation packages and you could score some excellent off-season deals.
How many days is enough for Chupacallos?
The ideal duration for your Chupacallos vacation depends on what you'd like to see. Generally, a few days to a week will give you time to hit all the top attractions and discover some hidden treasures along the way.
How to find the best Chupacallos package deals?
Use Expedia's handy filters to find some great Chupacallos package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chupacallos 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 usually best to book your vacation package as soon as possible.
Is it cheaper to book a Chupacallos vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can personalize your Chupacallos getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chupacallos?
If you're planning a spur-of-the-moment Chupacallos getaway, check out 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 sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Chupacallos?

  1. Choose when to travel: Check your diary and get packing. Your preferred season and the activities on offer will also help you decide when to escape to Chupacallos.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Chupacallos.
  3. Organize your Chupacallos escape with our trip planning tool: Search for and book stays and activities all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Chupacallos together.
  4. Work out your trip length: Consider how long you want to spend discovering Chupacallos. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  5. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the right Chupacallos vacation package for you.
  6. Book any excursions or activities: Here's the fun part — locking in everything you want to see and do. Explore some of the incredible things to do in Chupacallos and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Chupacallos vacation packages?
Set off on your ideal getaway to Chupacallos with Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.