
Chupacallos Holidays
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Top Flight + Hotel Deals in Chupacallos
Price found within the past 48 hours. Click for updated prices.

Urbana Hotel
San Juan Antiguo
Price was €1,353, price is now €847 per person
€847
per person
7 Mar - 14 Mar
found 20 hours ago
Return flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (389 reviews)
Good location to go any part. The building is safe, good gates and security camaras all over. Room was clean ac good. No mcrowave or coffee in the hotel.
Reviewed on 11 Jan 2026

OLV Fifty Five - Adults Only
Condado
Price was €2,791, price is now €1,577 per person
€1,577
per person
7 Mar - 14 Mar
found 20 hours ago
Return flight included
Boston (BOS) to San Juan (SJU)
8.6/10 Excellent! (577 reviews)
It was a great Stay, very nice and great customer service from the staff. Jessica, front desk worker was amazing. Kelvin
Reviewed on 9 Jan 2026

The Oliver Hotel
San Juan Antiguo
Price was €1,527, price is now €914 per person
€914
per person
7 Mar - 14 Mar
found 20 hours ago
Return flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (50 reviews)
Definitely a different experience to not have a ton of amenities or staff on site at all times as they manage multiple properties. That being said, they were always a quick text or phone call away and everyone was extremely friendly and helpful. Great location and very clean room. I would definitely recommend this spot for the next traveler looking for a great (and walkable) place to stay near Old San Juan and/or Condado.
Reviewed on 5 Jan 2026


Olive Boutique Hotel, A Small Luxury Hotel of the World (Adults Only)
Condado
Price was €2,620, price is now €1,591 per person
€1,591
per person
7 Mar - 14 Mar
found 20 hours ago
Return flight included
Boston (BOS) to San Juan (SJU)
9/10 Wonderful! (645 reviews)
We had a great stay at O:live boutique hotel. I’m sorry we didn’t have more time to explore the restaurant, pool, etc but this was a one night stay pre-cruise and we already had dinner reservations off-property. Check in was quick and efficient, the front desk staff was very pleasant. The lobby is cozy and intimate - as is the whole hotel. Our room 203 was a nice surprise - it had a big private courtyard with lounge seating, cafe table and chairs, and a really cool outdoor tub/shower. The bedding was very comfortable, the bathroom clean and modern. I would definitely stay here again and I would set aside some time to experience the pool, restaurant, etc.
Reviewed on 10 Jan 2026
Top hotels in Chupacallos

Hyatt Regency Grand Reserve Puerto Rico
200 Coco Beach Blvd. Highway 955-I Río Grande
Fully refundableReserve now, pay when you stay
The price is €472 per night from 20 Jan to 21 Jan
€472
20 Jan - 21 Jan
includes taxes & fees
9/10 Wonderful! (2,868 reviews)
Great
Reviewed on 9 Jan 2026

El Conquistador Resort
1000 Conquistador Avenue Fajardo
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (3,203 reviews)
A lot of amenities, golf, tennis, pickle ball, ferry to private beach with restrooms/restaurant/beach volleyball and more. Live music every night we were here. Many restaurants, which were about average. Close to El Yunque rainforest and other marinas from which to launch snorkeling trips.
Reviewed on 8 Jan 2026

Wyndham Grand Rio Mar Rainforest Beach and Golf Resort
6000 Rio Mar Boulevard Río Grande
Fully refundableReserve now, pay when you stay
The price is €745 per night from 5 Feb to 6 Feb
€745
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (2,262 reviews)
Great property that did not feel too crowded. Excellent dining options, very nice beach and multiple pools. Very friendly staff. We definitely would recommend this hotel!
Reviewed on 8 Jan 2026
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

El Yunque Rainforest: Waterslides, Waterfalls and Rope Swing
€21
per adult
84% of travellers recommend

Culebra Day Trip from Fajardo by Catamaran
€138
per adult
92% of travellers recommend

All Inclusive Beach and Snorkel Boat Tour to Icacos Island
€119
per adult
94% of travellers recommend
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