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Estreito da Calheta Vacation Packages

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Estreito da Calheta Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pestana Ocean Bay Resort

Pestana Ocean Bay Resort

4 out of 5
Price was $1,236, price is now $1,067 per person
$1,067
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this beach hotel in Funchal. Enjoy free WiFi, a beach locale, and a marina. Popular attractions Funchal Marina and Praca do Municipio are located nearby.
Carla and the management team was excellent.

Reviewed on Aug 14, 2026

Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

4 out of 5
Price was $2,350, price is now $1,776 per person
$1,776
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this beach hotel in Santa Cruz. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Funchal Farmers Market and Praca do Municipio are located nearby.

Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $2,108, price is now $1,602 per person
$1,602
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this luxury hotel in Funchal. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Funchal Marina and Praca do Municipio are located nearby.
Good basic 4 star hotel, as a base with a pool and breakfast it was fine for us. As long as a little tired decor doesn’t trigger you you’ll be great. Location is fantastic with a small park next door, shopping centre 5mins walk away and dozens of bars and restaurants nearby.

Reviewed on Aug 6, 2026

Pestana Miramar Garden & Ocean Resort

Pestana Miramar Garden & Ocean Resort

4 out of 5
Price was $2,056, price is now $1,642 per person
$1,642
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this spa hotel in Funchal. Enjoy free WiFi, a full-service spa, and a fitness center. Popular attractions Lido Bathing Complex and Funchal Marina are located nearby.
We really enjoyed staying at this hotel - quiet peaceful setting in beautiful gardens. Would definitely return.

Reviewed on Jul 13, 2024

Moon & Sun Funchal

Moon & Sun Funchal

4 out of 5
Price was $1,839, price is now $1,471 per person
$1,471
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this hotel in Funchal. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Funchal Marina and Praca do Municipio are located nearby.

Pestana Churchill Bay

Pestana Churchill Bay

4 out of 5
Price was $1,847, price is now $1,491 per person
$1,491
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Stay at this hotel in Camara de Lobos. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Formosa Beach and Lido Bathing Complex are located nearby.

Aqua Natura Bay

Aqua Natura Bay

4 out of 5
Price was $1,733, price is now $1,516 per person
$1,516
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this spa hotel in Porto Moniz. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Porto Moniz Natural Pools and Lava Pools are located nearby.

Sé Boutique Hotel

Sé Boutique Hotel

4 out of 5
Price was $1,485, price is now $1,304 per person
$1,304
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Book a stay at this spa hotel in Funchal. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Praca do Municipio and Funchal Marina are located nearby.

Estreito da Calheta Vacation Packages 3-4 Night Stays

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

Pestana Churchill Bay

4 out of 5
Price was $1,236, price is now $1,057 per person
$1,057
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $1,553, price is now $1,236 per person
$1,236
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

4 out of 5
Price was $1,785, price is now $1,448 per person
$1,448
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Ocean Bay Resort

Pestana Ocean Bay Resort

4 out of 5
Price was $1,236, price is now $1,067 per person
$1,067
per person
Nov 10 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)

Estreito da Calheta Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Moon & Sun Funchal

Moon & Sun Funchal

4 out of 5
Price was $1,839, price is now $1,471 per person
$1,471
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

4 out of 5
Price was $2,350, price is now $1,776 per person
$1,776
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

5 out of 5
Price was $2,108, price is now $1,602 per person
$1,602
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
Pestana Miramar Garden & Ocean Resort

Pestana Miramar Garden & Ocean Resort

4 out of 5
Price was $2,056, price is now $1,642 per person
$1,642
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)

Top Flight Deals

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

TAP Portugal
Fri, Nov 27 - Sun, Dec 13
LIS
Humberto Delgado
FNC
Cristiano Ronaldo
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select TAP Portugal flight, departing Fri, Nov 27 from Humberto Delgado to Cristiano Ronaldo, returning Sun, Dec 13, priced at $98 found 2 days ago
easyJet
Mon, Nov 30 - Fri, Dec 11
LIS
Humberto Delgado
FNC
Cristiano Ronaldo
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select easyJet flight, departing Mon, Nov 30 from Humberto Delgado to Cristiano Ronaldo, returning Fri, Dec 11, priced at $111 found 2 days ago
Condor
Sun, Sep 27 - Sat, Oct 3
FRA
Frankfurt Intl.
FNC
Cristiano Ronaldo
$466 Roundtrip, found 2 days ago
$466
Roundtrip
found 2 days ago
Select Condor flight, departing Sun, Sep 27 from Frankfurt Intl. to Cristiano Ronaldo, returning Sat, Oct 3, priced at $466 found 2 days ago
TAP Portugal
Tue, Nov 17 - Thu, Nov 26
EWR
Newark Liberty Intl. Airport
FNC
Cristiano Ronaldo
$626 Roundtrip, found 10 hours ago
$626
Roundtrip
found 10 hours ago
Select TAP Portugal flight, departing Tue, Nov 17 from Newark Liberty Intl. Airport to Cristiano Ronaldo, returning Thu, Nov 26, priced at $626 found 10 hours ago