Estreito da Calheta Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Estreito da Calheta Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pestana Casino Park Ocean and SPA Hotel

Pestana Casino Park Ocean and SPA Hotel

CA $2,081
per person
Oct 31 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Funchal (FNC)
8.6/10 Excellent! (1,000 reviews)
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 Grand Premium Ocean Resort

Pestana Grand Premium Ocean Resort

CA $2,525
per person
Oct 4 - Oct 10
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Funchal (FNC)
9/10 Wonderful! (589 reviews)
Villa in Porto da Cruz With Ocean Views

Villa in Porto da Cruz With Ocean Views

CA $2,892
per person
Oct 9 - Oct 15
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Funchal (FNC)
No reviews
Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

CA $2,240
per person
Oct 13 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Funchal (FNC)
9.2/10 Wonderful! (283 reviews)
Pestana Carlton Madeira Ocean Resort Hotel

Pestana Carlton Madeira Ocean Resort Hotel

CA $2,106
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Funchal (FNC)
9/10 Wonderful! (1,002 reviews)
Loved the pool area and access to ocean fantastic

Reviewed on Aug 14, 2026

Ready to book your vacation to Estreito da Calheta?

Choose your dates

Estreito da Calheta Hotel Deals

 Saccharum Resort

Saccharum Resort

Rua Serra de Água, 1 Calheta
Fully refundable
CA $487
CA $513 total
Sep 21 - Sep 22
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Great stay. Loved the location and ocean access."

Reviewed on Aug 21, 2026

Saccharum Resort
Savoy Palace - The Leading Hotels of the World - Savoy Signature

Savoy Palace - The Leading Hotels of the World - Savoy Signature

Avenida do Infante, 25 Funchal
Fully refundable
CA $695
CA $730 total
Sep 1 - Sep 2
includes taxes & fees
Savoy Palace - The Leading Hotels of the World - Savoy Signature
Reid's Palace, A Belmond Hotel, Madeira

Reid's Palace, A Belmond Hotel, Madeira

Estrada Monumental 139 Funchal
Fully refundableReserve now, pay when you stay
CA $1,205
CA $1,260 total
Sep 17 - Sep 18
includes taxes & fees
9.8/10 Exceptional! (639 reviews)
"Beautiful well kept property. Kid friendly. Everyone that worked there was friendly and went above and beyond. A true Gem!"

Reviewed on Aug 23, 2026

Reid's Palace, A Belmond Hotel, Madeira
See all 4,602 properties in Estreito da Calheta
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.

What to do in Estreito da Calheta

Nuns Valley Tour

Nuns Valley Tour

CA $40
per adult
Nuns Valley Tour
Caldeirão Verde Levadas Walk in Madeira

Caldeirão Verde Levadas Walk in Madeira

CA $77
per adult
Caldeirão Verde Levadas Walk in Madeira
Aerial view of Cabo Girão Island

Funchal Hop-On Hop-Off Câmara de Lobos & Cabo Girão 5 Days

CA $46
per adult
100% of travellers recommend
Funchal Hop-On Hop-Off Câmara de Lobos & Cabo Girão 5 Days
See all activities in Estreito da Calheta

Frequently asked questions

How much does an Estreito da Calheta vacation package cost?
You can snap up a vacation package to this destination from CA $2,081 on Expedia. But how much your vacation to Estreito da Calheta costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Estreito da Calheta?
To score cheap Estreito da Calheta vacation packages, organize your getaway outside of peak periods such as school holidays. You'll typically find better availability and lower prices for hotels and flights.
How many days is enough for Estreito da Calheta?
Estreito da Calheta vacations come in many shapes and sizes, but to really get a feel for this destination, we'd suggest 7 days is a good ballpark. With this timeframe, you can fit in major attractions like 25 Fontes and Cascada da Risco and Casa das Mudas Arts Centre as well as hidden gems. Don't miss out on cool areas such as Lombo do Doutor and Canhas either. If you plan wisely, you can even take a day trip outside of Estreito da Calheta too.
How to find the best Estreito da Calheta package deals?
Finding a cheap Estreito da Calheta package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Estreito da Calheta package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Estreito da Calheta vacation as a package?
You can enjoy significant savings on your Estreito da Calheta getaway by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Estreito da Calheta?
If you're considering an impromptu Estreito da Calheta trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Estreito da Calheta?
  1. Choose the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Estreito da Calheta.
  2. Calculate your budget: Make sure you have enough money to cover everything from food and transportation to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Estreito da Calheta.
  3. Decide your trip length: Consider how much time you want to spend exploring Estreito da Calheta. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Estreito da Calheta vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.