Search Deals onCalheta Vacation Packages
Calheta Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Casa d'Avó Guesthouse
Price was $754, price is now $734 per person
$734
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Book a stay at this business-friendly guesthouse in Velas. Enjoy free WiFi, free parking, and room service. Popular attractions Pico da Esperanca and Velas Marina are located nearby.

Hotel da Graciosa
Price was $995, price is now $889 per person
$889
per person
Oct 28 - Nov 3
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Book a stay at this spa hotel in Santa Cruz da Graciosa. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Velho do Monte d'Ajuda and Centro Cultural de Santa Cruz da Graciosa are located nearby.
Hotel is nice, check-in was quick and easy. All was clean and stafg was extremely helpful.
Location is close to the little marina with a beach, pretty much across the local road from the hotel.
Unfortunately, we did not have time to check the sauna.
Reviewed on Jul 26, 2026

Casa Lagar de Pedra T3
Price was $1,237, price is now $1,149 per person
$1,149
per person
Oct 26 - Nov 1
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this apartment in Santa Cruz da Graciosa. Enjoy a garden. Popular attractions Centro Cultural de Santa Cruz da Graciosa and Velho do Monte d'Ajuda are located nearby.

Cabanas da Viscondessa
Price was $1,953, price is now $1,827 per person
$1,827
per person
Oct 4 - Oct 10
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this hotel in Velas. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Velas Marina and Igreja de Sao Jorge are located nearby.
It was a perfect place to explore the island. Staff was super friendly and very helpful. A very peaceful place, would highly recommend. Would definitely come back and stay there again.
Reviewed on Jul 15, 2026

Casa Lagar de Pedra T2
Price was $1,166, price is now $1,092 per person
$1,092
per person
Oct 26 - Nov 1
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this apartment in Santa Cruz da Graciosa. Popular attractions Centro Cultural de Santa Cruz da Graciosa and Velho do Monte d'Ajuda are located nearby.

Quinta da Magnólia
Price was $2,014, price is now $1,896 per person
$1,896
per person
Oct 4 - Oct 10
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this hotel in Velas. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Pico da Esperanca and Velas Marina are located nearby.
The property is situated in a beautiful location and very close to the airport. The staff was super helpful and kind. Breakfast was delicious. Room was big with great view. I would advise to bring your own toiletries. It only has shower cap and soap. I was prepared so it wasn't a big deal.
Reviewed on Aug 4, 2026

Make It Happen Farm
Price was $823, price is now $803 per person
$803
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this farm stay in Velas. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Velas Marina and Igreja de Sao Jorge are located nearby.
An overall nice experience for something different. Would stay again.
Strengths: Well located with a nice view of Pico and the ocean. Well done appointed rooms with comfortable beds. Amenities such as laundry, drying racks, tea kettles, bikes, and common room. Fresh bread and local cheese were great. Store with many staples. Animals to pet and feed.
Opportunities: Noise from nearby construction and operating business plus neighboring dogs was distracting. One egg each for included breakfast.
Reviewed on Jun 27, 2026

Casas dos Vimes
Price was $1,568, price is now $1,533 per person
$1,533
per person
Oct 4 - Oct 10
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
Stay at this cottage in Calheta. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Fajã dos Cubres are located nearby.
Wonderful cozy house with a fully equipped kitchen. The food supplied on our arrival was unexpected and appreciated as we arrived later than expected. Quiet, friendly community right near the ocean with trails within walking distance of the home.
Reviewed on Apr 14, 2024
Calheta Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Calheta Vacation Packages 5-7 Night Stays
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