Chupacallos Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Top Chupacallos Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ola Boutique Hotel
Condado
CA $3,160
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to San Juan (SJU)
9/10 Wonderful! (1,019 reviews)
The staff was amazing! Friendly and welcoming! Answers all your questions, decent location! Street parking is available but hard to find. Shower was fun, but the water leaks into the room. Other than that, there’s a pool table in the lobby, and cute little restaurant at the front.
Reviewed on Oct 22, 2026
WALD HAUS by DW
CA $6,474
per person
Jan 1 - Jan 8
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Juan (SJU)
9.2/10 Wonderful! (11 reviews)
The home itself is absolutely stunning but the road to the villa is not just narrow, it's washed out in many places, we struggled to navigate the potholes even with a jeep and an SUV, I would not drive it at night. There are great amenities like the fridge and bathroom downstairs, the coffee / cocktail bar is fabulous.The kitchen was well-stocked with basic spices and supplies but it was crawling with roaches. Wifi is spotty so be sure to have the guidebook downloaded and screenshots of the phone number to call because the phone number posted throughout the villa is not functioning. Even in August the combination of ACs, fans, and breezes kept the temprature very comfortable. Excellent pool, though very little shallow area, if you're traveling with kids or weaker swimmers.
Reviewed on Aug 13, 2026
Hipodromo by Otium
Santurce
CA $1,312
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to San Juan (SJU)
7/10 Good! (7 reviews)
The stay was clean and the beach is close by. Owners were easy to communicate with and answered every question quick!
Reviewed on Sep 26, 2026
Ready to book your vacation to Chupacallos?
Chupacallos Hotel Deals
Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
CA $368
CA $474 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (3,509 reviews)
"Third time staying here, twice in a room and this time in a villa. Phenomenal experience as always!"
Reviewed on Oct 24, 2026
El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
CA $440
CA $579 total
Oct 26 - Oct 27
includes taxes & fees
9.2/10 Wonderful! (3,662 reviews)
"Palomino Island tops the best item. Parking service is its worst."
Reviewed on Oct 24, 2026
Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
CA $381
CA $524 total
Oct 26 - Oct 27
includes taxes & fees
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.
What to do in Chupacallos
Culebra Day Trip from Fajardo by Catamaran
CA $235
per adult
92% of travellers recommend
El Yunque Rainforest Guided Hiking Tour
CA $124
per traveller
96% of travellers recommend
All-Inclusive Culebra Beach & Snorkel Adventure
CA $216
per adult
88% of travellers recommend
Frequently asked questions
How much does a Chupacallos vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,231 on Expedia. However, how much your vacation to Chupacallos costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chupacallos?
August, September and October are the best times to look for cheap Chupacallos vacation packages. Opting to travel in quieter periods means you can typically find better prices on flights and hotels.
How many days is enough for Chupacallos?
With around 2 days, you'll have enough time to enjoy popular neighbourhoods such as Machos and Barrio Pueblo during your Chupacallos vacation. Remember to also add Splash Tattoo and Playa Medio Mundo to your must-see list. Searching for more adventures? Consider exploring outside of Chupacallos on day trips and tours.
How to find the best Chupacallos package deals?
Use Expedia's handy filters to find some terrific Chupacallos package deals. When you begin your search, just 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 low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically 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 score you significant savings when compared to arranging hotels and flights individually. Better still, you can tailor your Chupacallos escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Chupacallos?
If you're planning an impromptu Chupacallos vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chupacallos?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Chupacallos.
- Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Chupacallos.
- Determine how many days away: Start by listing all the activities and attractions you'd like to experience in Chupacallos. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, lock in the right Chupacallos vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
