Calheta Vacation Packages 2025/2026 from $1,081

Calheta flight + hotel vacation packages

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

Pestana Casino Park Ocean and SPA Hotel

$1,081

per person

Feb 4 - Feb 9

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

This smoke-free hotel features a casino, a full-service spa, and a nightclub. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy a meal in one of the 3 restaurants and perks like free WiFi.

Pestana Royal All Inclusive Ocean & Spa Resort

$1,195

per person

Feb 4 - Feb 9

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

This all-inclusive hotel features 2 outdoor pools and 2 bars/lounges. 4 restaurants and a poolside bar offer options for onsite dining and unwinding.

The Views Oasis - Family Friendly

$1,156

per person

Feb 4 - Feb 9

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Bring the family and enjoy the mini golf, children's pool, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and free self parking.

The Views Baia - Adults Only

Sao Pedro

$1,122

per person

Feb 4 - Feb 9

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

Pestana Quinta Perestrello

$3,968

per person

Dec 28 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Funchal (FNC)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the indoor pool and free perks like buffet breakfast and WiFi in public areas. Self parking and a garden are also offered on site.

Top Calheta hotels deals

Saccharum Resort

Rua Serra de Água, 1 Calheta

Free Cancellation

Reserve now, pay when you stay

$231 nightly

$244 total

Nov 22 - Nov 23

Total with taxes and fees

This luxury hotel features a full-service spa, a marina, and 2 restaurants. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. There's fun for all ages with a children's pool and an arcade/game room, and babysitting is an added bonus.

Pool

Spa

Calheta Beach - All Inclusive

Av. D. Manuel I - n.3 Calheta

Free Cancellation

Reserve now, pay when you stay

$220 nightly

$234 total

Dec 11 - Dec 12

Total with taxes and fees

A full-service spa, 3 restaurants, and an outdoor pool are all featured at this all-inclusive property. There's fun for all ages with a free kid's club and a children's pool, and babysitting is an added bonus. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like buffet breakfast and WiFi in public areas.

Pool

Breakfast included

Boutique Hotel Jardim do Mar

Sitio da Piedade 37, Calheta, Madeira

Get rates

A restaurant and an outdoor pool are featured at this hotel. Guests will appreciate free perks like full breakfast and WiFi in public areas. A coffee shop and luggage storage are also provided.

Pool

Breakfast included

Hotel Jardim Atlantico

Caminho Lombo da Rocha, 1 Prazeres, Calheta, Calheta

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A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Families will appreciate the arcade/game room and complimentary bicycles. Enjoy the indoor pool and perks like free self parking and a free beach shuttle.

Pool

Hot Tub

Socalco Nature Calheta

Caminho do Lombo do Salão, 13, Calheta, Madeira

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An outdoor pool, free self parking, and barbecue grills are featured at this farm stay. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden and a picnic area are also provided.

Pool

Breakfast included

Home for Nature Tourism, Madeira Island LAURISHOUSE, Nature and Sea

Prazeres Madeira

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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.

Pool

Kitchen

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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.

Popular places to visit

Casa das Mudas Arts Center

You can spend time browsing the exhibits at Casa das Mudas Arts Center during your trip to Calheta. Wander the seaside in this relaxing area.

Eglise de Faja da Ovelha

You can learn about the history of Faja da Ovelha with a visit to Eglise de Faja da Ovelha. Wander the seaside in this relaxing area.

25 Fontes and Cascada da Risco

Commune with nature and explore the great outdoors at 25 Fontes and Cascada da Risco during your travels in Calheta. Wander the seaside in this relaxing area.

Frequently asked questions

How much are vacation packages to Calheta?

With vacation packages available from as low as $1,081, you won't need to max out the credit card for your trip to Calheta. Travelocity can help. Bundle up hotels, flights and tours into a package and walk away with exciting discounts. The more you book, the greater the savings.

Where can I get the best vacation package deals for Calheta?

For a fun and affordable Calheta package deal, nothing compares to Travelocity. Select from 400 airlines and 1,000,000 properties around the world to create the ideal trip — it couldn't be simpler.

Why should I book my Calheta vacation bundle via Travelocity?

Because you'll never wander on your own if you book your vacation with us, and we offer round-the-clock support and exceptional service to boot. Add to that our Price Match Guarantee and countless destinations and experiences to choose from. We're here to make your daydreams a reality.

Will I save money on my Calheta car rental if I bundle it with my hotel or flight?

Combining your bookings into a Calheta vacation package will leave you with some serious savings. Bundle a car and flight; a car, hotel and flight; or a car and hotel. You won't find a better way to discover the greater Calheta region than with your own ride. You can also add activities and experiences to your Travelocity package.