Calheta Vacations from $1,636

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Your Calheta Vacation

Say farewell to the hassle of planning and hello to a Calheta vacation package. With everything organized before you take off, you can focus on discovering this city, starting with Achadas da Cruz, which is good for views, hiking and nature. You'll want to do some exploring during your trip to Calheta. Carve out some time for major attractions such as Ponta Do Sol Beach, Paul do Mar Beach and 25 Fontes and Cascada da Risco. Stop daydreaming and start adventuring. Browse the broad range of options on Expedia today and put your Calheta vacation plans in motion!

The Latest Calheta vacation packages

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

Pestana Casino Studios

$1,636
per person
Sep 21 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
9.2/10 Wonderful! (74 reviews)
GOOD LOCATION

Reviewed on Apr 1, 2026

Pestana Carlton Madeira Ocean Resort Hotel

Pestana Carlton Madeira Ocean Resort Hotel

Save 100% on your flight
$2,293
per person
Sep 27 - Oct 3
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Funchal (FNC)
8.8/10 Excellent! (1,000 reviews)
Loved the pool area and access to ocean fantastic

Reviewed on Aug 14, 2026

Pestana Royal All Inclusive Ocean & Spa Resort

Pestana Royal All Inclusive Ocean & Spa Resort

$2,002
per person
Sep 27 - Oct 3
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Funchal (FNC)
8.2/10 Very Good! (141 reviews)
Everything was wonderful!

Reviewed on Aug 14, 2026

Hotel Riu Madeira - All Inclusive

Hotel Riu Madeira - All Inclusive

$1,709
per person
Oct 18 - Oct 24
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Funchal (FNC)
9.2/10 Wonderful! (283 reviews)
Pestana Promenade Ocean Resort Hotel

Pestana Promenade Ocean Resort Hotel

$1,856
per person
Sep 27 - Oct 3
found 22 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Funchal (FNC)
9.2/10 Wonderful! (691 reviews)
Good

Reviewed on May 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Calheta
View all trips

Stay near popular Calheta attractions

25 Fontes and Cascada da Risco

9.4/10 (16 reviews)
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.
See properties

Eglise de Faja da Ovelha

8.4/10 (15 reviews)
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.
See properties

Casa das Mudas Arts Center

7.6/10 (5 reviews)
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.
See properties

Levada Pedregal

8.0/10 (2 reviews)
Commune with nature and explore the great outdoors at Levada Pedregal during your travels in Ponta do Pargo.
See properties

Ponta do Pargo Lighthouse

9.0/10 (4 reviews)
You can find out about the history of Ponta do Pargo with a visit to Ponta do Pargo Lighthouse.
See properties

beach near Serra de Água

Why not spend a lazy afternoon at beach near Serra de Água during your trip to Lombo do Doutor?
See properties

beach near Jardim do Mar

Why not spend a lazy afternoon at beach near Jardim do Mar during your trip to Jardim do Mar?
See properties

What to do in Calheta

Caldeirão Verde Levadas Walk in Madeira

Caldeirão Verde Levadas Walk in Madeira

$55
per adult
Caldeirão Verde Levadas Walk in Madeira
Nuns Valley Tour

Nuns Valley Tour

$28
per adult
Nuns Valley Tour
Aerial view of Cabo Girão Island

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

$32
per adult
100% of travellers recommend
Funchal Hop-On Hop-Off Câmara de Lobos & Cabo Girão 5 Days
See all activities in Calheta

Calheta Hotel Deals

 Saccharum Resort

Saccharum Resort

Rua Serra de Água, 1 Calheta
Fully refundableReserve now, pay when you stay
$370 nightly
$390 total
Sep 13 - Sep 14
Total with taxes and fees
9.4/10 Exceptional! (1,003 reviews)
"Nice hotel, good location…I booked for 2 adults and 1 child, but there was no bed / towels etc for the child. The first bed they brought was tiny and had a rather sharp spike sticking out, the second attempt at the child’s bed was better, and eventually we were given towels for the child. We weren’t ..."

Reviewed on Aug 8, 2026

Saccharum Resort
Calheta Beach - All Inclusive

Calheta Beach - All Inclusive

Av. D. Manuel I - n.3 Calheta
Fully refundableReserve now, pay when you stay
$366 nightly
$385 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (343 reviews)
"Excellent facilities, nice and clean. Staff is very helpful. I would make more fish/seafood choices at the buffet and less meat. Also, the actual beach which I understand ids not really the hotel’s property is there, but the water is not very clean. But the swimming pool is great. In genrral, excellent ..."

Reviewed on Aug 15, 2026

Calheta Beach - All Inclusive
Boutique Hotel Jardim do Mar

Boutique Hotel Jardim do Mar

Sitio da Piedade 37 Calheta Madeira
9.2/10 Wonderful! (63 reviews)
"We stayed here for two nights in Jardim do Mar and overall had a pleasant experience. The hotel is in a very pretty location, set in a quaint little square and not far from the beach, which was lovely. The hotel itself is fairly modern and comfortable. The only downside was on the second night when ..."

Reviewed on Jul 1, 2026

Get rates
Boutique Hotel Jardim do Mar
See all 921 properties in 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.

Find the Best Calheta Vacation Packages

Calheta Beach Vacation

Listen to the sound of waves hitting the shore and stroll by the shimmering waters during your Calheta vacation. If you need an escape from everyday life, a trip to Calheta is just what the doctor ordered. We have plenty of Calheta vacation packages to pick from. Snap one up near Paul do Mar Beach, just 4 miles (7 km) from the center of town, and live out your vacation fantasies without hurting your budget.

Things You Should Know About Calheta

  • If you think a perfect escape is fresh sea air and walks along the shore, check out our Calheta beach hotels. You're sure to forget the headaches of daily life at these perfectly located retreats.
  • Our private vacation homes, including Villa São Lourenço by MHM and Atlantic Pearl Villa - ETC Madeira, are a hit with travelers of all sorts. Check out the amenities and get ready for your vacation in Calheta!
  • There are lots of activities that keep the 1,600 or so residents of Calheta occupied. A quick browse of our Calheta things to do page will show you what this place has to offer.
  • Paul do Mar Beach, 25 Fontes and Cascada da Risco and Eglise de Faja da Ovelha are some great sights that should be on your must-do list. With our Calheta vacation deals, you'll have more money in your back pocket to explore.

Calheta Essential Information

Language
Portuguese
Currency
Euros
Local Welcome
Olá
Local Goodbye
Adeus
Closest Airport
Cristiano Ronaldo Airport (FNC)
Population
1,600
Max Temp Winter
65ºF
Max Temp Summer
70ºF
Top Sights
Ponta Do Sol Beach, Caves of Sao Vicente and Volcanism Center and 25 Fontes and Cascada da Risco

More vacations you might like

Frequently asked questions

How much does a Calheta vacation package cost?
You can pick up a vacation package to this destination from $1,636 on Expedia. However, how much your vacation to Calheta costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Calheta?
If you'd like to snag a cheap Calheta vacation package, consider planning a trip in July, November and December. You're likely to find better prices on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Calheta?
When planning your Calheta vacation, a few days will be enough to tour all the highlights. Make sure to visit Eglise de Faja da Ovelha — it's one of the major sights in this destination. If you want more activities, think about basing yourself here and heading off on some tours from Calheta.
How to find the best Calheta package deals?
Use Expedia's filter tool to help you find some of the best Calheta package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Calheta package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Calheta vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights separately. Better still, you can tailor your Calheta escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Calheta?
If you're considering a spur-of-the-moment 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 land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Calheta?
  1. Choose when to travel: Check your calendar and pack your bags. Your favorite season and the type of activities available will also help you decide when to visit Calheta.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your accommodations will probably be the largest expense during your trip to Calheta.
  3. Explore Calheta using Expedia's trip planning tool: Gain insights into the top attractions and best hotels for your trip to Calheta. You can also save your favorite places, collaborate with your group and organize all your plans in one place.
  4. Decide how many days away: Start by listing all the attractions and activities you want to get to in Calheta. Then, estimate how long you'll need for each, as well as any travel time.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Calheta vacation package that brings all your bookings together.
  6. Book any activities or excursions: Now to the fun part — organizing everything you want to see and do. Browse some of the exciting things to do in Calheta in Calheta and reserve your tickets in advance to save time (and maybe some cash too!).
Does Expedia offer Book Now, Pay Later Calheta vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Calheta break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.