Pico Island Vacation Packages 2026 from $811

Photo by Brian Scrivner

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Pico Island vacation packages

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

Sara Village

$811

per person

Nov 6 - Nov 9

found 22 hours ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

8.4/10 Very Good! (66 reviews)

We did not stay and cancellation was not accepted.

Reviewed on Aug 6, 2026

Adegas do Pico

$854

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

9/10 Wonderful! (40 reviews)

Wonderful location as a home base to explore the island. Very clean, super helpful staff, and the view was amazing!

Reviewed on Aug 22, 2026

35th Atlantic View

$1,064

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

8.4/10 Very Good! (43 reviews)

Casa do Porto Santa Cruz B&B

$881

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

No reviews

A Casa do Ouvidor

$1,003

per person

Dec 6 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pico Island (PIX)

9.6/10 Exceptional! (33 reviews)

There is no hottub at this property! We were really disappointed to see this when we arrived as it was one of the main reasons we booked here. The property need to update their expedia profile but please note there hasnt been a hottub there in a while. Otherwise, beautiful view and a nice stay at the property. A bit rough around the edges in places but perfectly adequate for our 4 night stay

Reviewed on Jun 9, 2026

Don't see what you're looking for?

See all available trips from Columbus to Pico Island

View all trips

Stay near popular Pico Island attractions

Mount Pico

9.2/10 (65 reviews)

Commune with nature and explore the great outdoors at Mount Pico during your travels in São Caetano. Discover the area's mountain views and sunrises.

See properties

Pico Island Vineyard Culture

9.0/10 (44 reviews)

You can enjoy a tasting or tour at Pico Island Vineyard Culture during your travels to Criação Velha. While you're in the area, stroll along the marina.

See properties

São João Forest Reserve

9.2/10 (21 reviews)

Explore the great outdoors at São João Forest Reserve, a lovely green space in São João.

See properties

Azores Wine Company

You can enjoy a tasting or tour at Azores Wine Company during your travels to Bandeiras.

See properties

Museu do Vinho

8.8/10 (12 reviews)

You can spend time exploring the galleries in Museu do Vinho in Madalena. While you're in the area, stroll along the marina.

See properties

Gruta das Torres

9.0/10 (26 reviews)

Explore the great outdoors at Gruta das Torres, a lovely green space in Criação Velha. While you're in the area, stroll along the marina.

See properties

Caiado Lagoon

8.4/10 (14 reviews)

Explore the great outdoors at Caiado Lagoon, a lovely green space in Lajes do Pico. While you're in the area, stroll along the seaside.

See properties

Sao Roque Church

8.6/10 (10 reviews)

After visiting Sao Roque Church, make a plan to see the other sights and activities in Sao Roque do Pico. While you're in the area, stroll along the seaside.

See properties

What to do in Pico Island

Happy Cows Buggy Tour

$353

per traveler

Picture 10 for Activity Horta, Faial: University based Whale & Dolphin Expedition

Horta, Faial: Research Whale & Dolphin Expedition

$104

per adult

100% of travellers recommend

Whale and Dolphin Watching in Pico Island - Half Day

$83

per adult

See all activities in Pico Island

Pico Island Hotel Deals

Vinhas do Calhau

Porto do Calhau 42 Madalena Madalena

$139 nightly

$144 total

Oct 24 - Oct 25

Total with taxes and fees

9.6/10 Exceptional! (63 reviews)

"The bungalow was very spacious and well equipped. Unfortunately, there was neither a table nor sunbeds on the terrace. Breakfasts were very simple, with a limited selection of food."

Reviewed on Sep 18, 2026

Hotel Caravelas

Rua Conselheiro Terra Pinheiro, 3 Madalena

$101 nightly

$105 total

Sep 28 - Sep 29

Total with taxes and fees

8/10 Very Good! (248 reviews)

"Service was very good. Breakfast was excellent cleanliness was a five star. Location is just the best."

Reviewed on Sep 19, 2026

Azores Youth Hostels - Pico

Rua João Bento Lima Sao Roque do Pico

$29 nightly

$30 total

Oct 3 - Oct 4

Total with taxes and fees

8/10 Very Good! (46 reviews)

"The hostel is such a lovely place, very good located and the staff was really helpful, wherever you need they are always there to help you. Very nice and peaceful place. 100% recommended. The unic thing that I missed was a kitchen so you can cook your own food. But there are very nice local restaurants ..."

Reviewed on Sep 12, 2026

See all 393 properties in Pico Island

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.