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

Quinta Achada Fazenda
Price was $866, price is now $844 per person
$844
per person
Oct 29 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Stay at this apartment in Santa Cruz. Enjoy free WiFi, free parking, and 10 outdoor pools. Popular attractions Pedra Badejo Beach and Pedra Badejo Municipal Mall are located nearby.

Hotel Principal
Price was $927, price is now $882 per person
$882
per person
Oct 29 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Stay at this hotel in Tarrafal. Enjoy free breakfast, free WiFi, and free parking. Popular attractions lighthouse and Tarrafal Beach are located nearby.
Small, clean, efficient rooms. Noise was a major issue as rooms have no noise insulation to stop sounds from hallways. We could hear conversations in the hallway crystal clearly and we lost sleep over this until all guests were asleep. Breakfast was nice. They are trying their best. Nice location close to bakery and mini market.
Reviewed on Aug 20, 2025

Aparthotel Palace
Price was $1,580, price is now $1,505 per person
$1,505
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Stay at this hotel in Praia. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Estadio da Varzea and Quebra Canela Beach are located nearby.

Hotel Vulcão
Price was $956, price is now $915 per person
$915
per person
Oct 29 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Book a stay at this business-friendly hotel in Cidade Velha. Enjoy free WiFi, 2 outdoor pools, and 2 bars/lounges. Popular attraction Royal Fortress of São Filipe is located nearby.
Nothing to say
Reviewed on Jun 26, 2026

Pestana Trópico
Price was $1,156, price is now $1,116 per person
$1,116
per person
Sep 29 - Oct 2
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Book a stay at this beach hotel in Praia. Enjoy free WiFi, room service, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Prainha Beach and Centro Cultural Português are located nearby.
We had to return to this wonderful hotel for its 5-star tranquility. A home from home, smiling and approachable staff, and an environment you can truly relax in. The manager Ana was a delight to talk with, and it shows the culture of the place. I’m sure other hotels in Cidade Praia are good, but this place is special. Low-key luxury.
Reviewed on Aug 16, 2026

Vivi Hotel
Price was $1,401, price is now $1,362 per person
$1,362
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Stay at this hotel in Praia. Enjoy free WiFi, free parking, and 6 beach bars. Popular attractions Quebra Canela Beach and Centro Cultural Português are located nearby.
It’s a modest hotel easy access to the beaches and restaurants as well as Praia shopping. However no lifts, Wi-Fi connection is poor and bathroom ventilation is noisy.
The gym is next to the hotel but can be noisy in the morning.
The swimming pool is out of service at the moment due to refurbishment.
Reviewed on Jan 2, 2025

Hotel Cantinho
Price was $911, price is now $888 per person
$888
per person
Oct 29 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Stay at this hotel in São Salvador do Mundo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Porto Madeira and Espinho Branco are located nearby.
Tolle Lage sehr abgelegen und ruhig mitten in den schönen Bergen
Reviewed on Dec 6, 2025

Baia Verde Resort Tarrafal
Price was $945, price is now $922 per person
$922
per person
Oct 29 - Nov 2
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Santiago Island (RAI)
Book a stay at this beach hotel in Tarrafal. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Tarrafal Beach and lighthouse are located nearby.
Calheta de Sao Miguel Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Calheta de Sao Miguel Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Aug 23 - Thu, Sep 17
BOS
Logan Intl.
RAI
Praia Intl.
$829 Roundtrip, found 4 days ago
$829
Roundtrip
found 4 days ago

Sun, Aug 23 - Mon, Sep 14
BOS
Logan Intl.
RAI
Praia Intl.
$1,523 Roundtrip, found 2 hours ago
$1,523
Roundtrip
found 2 hours ago

Sun, Aug 23 - Mon, Sep 14
BOS
Logan Intl.
RAI
Praia Intl.
$2,068 Roundtrip, found 2 hours ago
$2,068
Roundtrip
found 2 hours ago

Sat, Aug 29 - Mon, Sep 14
BOS
Logan Intl.
RAI
Praia Intl.
$2,277 Roundtrip, found 5 days ago
$2,277
Roundtrip
found 5 days ago
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