Calheta Vacations from $941

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Your Calheta Vacation

The coastal scenery and spectacular views are just the beginning of the things Calheta has to offer. Enjoy the best parts of this interesting city your way with a customized Calheta vacation package. You'll want to do a little exploring during your trip to Calheta. Carve out some time for leading attractions such as Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge, Pico da Esperanca and Santa Bárbara Church. Your ideal Calheta vacation is just a few clicks away. Browse flights, accommodations and more on Expedia for an adventure that's tailored to suit your style.

The Latest Calheta vacation packages

Price found within the past 48 hours. Click for updated prices.
Casa do Zé - AL

Casa do Zé - AL

3 out of 5
Price was $970, price is now $941 per person
$941
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
9.6/10 Exceptional! (7 reviews)

Casa d'Avó Guesthouse

Casa d'Avó Guesthouse

3 out of 5
Price was $1,029, price is now $980 per person
$980
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
9.8/10 Exceptional! (55 reviews)
Our room had a patio with sliding doors overlooking the ocean! Gorgeous!!! There is a central kitchen that guests can use to make meals and lots of great places to sit. The staff are amazing. They help to call taxis, provide laundry service and any other help you may need. The owner came by regularly to check on how things were going and was easy to access.

Reviewed on Jul 11, 2026

Make It Happen Farm

Make It Happen Farm

3 out of 5
Price was $1,059, price is now $1,028 per person
$1,028
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sao Jorge Island (SJZ)
9.6/10 Exceptional! (14 reviews)
An overall nice experience for something different. Would stay again. Strengths: Well located with a nice view of Pico and the ocean. Well done appointed rooms with comfortable beds. Amenities such as laundry, drying racks, tea kettles, bikes, and common room. Fresh bread and local cheese were great. Store with many staples. Animals to pet and feed. Opportunities: Noise from nearby construction and operating business plus neighboring dogs was distracting. One egg each for included breakfast.

Reviewed on Jun 27, 2026

Casa Lagar de Pedra T2

Casa Lagar de Pedra T2

2 out of 5
Price was $2,413, price is now $2,216 per person
$2,216
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Sao Jorge Island (SJZ)
No reviews

Quinta da Magnólia

Quinta da Magnólia

3 out of 5
Price was $1,898, price is now $1,779 per person
$1,779
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Sao Jorge Island (SJZ)
9.8/10 Exceptional! (30 reviews)
The rooms and property are really lovely and quiet and the staff was very generous and wanted to make our stay special.

Reviewed on Jul 10, 2025

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Stay near popular Calheta attractions

Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge

9.6/10 (8 reviews)
Explore the great outdoors at Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge, a lovely green space in Calheta.
See properties

Calheta Hotel Deals

Azores Youth Hostels - São Jorge

Azores Youth Hostels - São Jorge

2 out of 5
Canada da Vinha Nova Calheta
$68 nightly
The price is $75 total per night from Jul 24 to Jul 25
$75 total
Jul 24 - Jul 25
Total with taxes and fees
8/10 Very Good! (22 reviews)
"Excellent location. Staff was friendly. Air conditioner was not working in our room and it was so hot to sleep. The staff tried but could not fix it. Breakfast was simple but fine. Very clean all around and well kept. View was incredible from the front shared spaces."

Reviewed on Jul 15, 2025

Azores Youth Hostels - São Jorge
Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Faja do Belo Calheta Azores
$307 nightly
The price is $324 total per night from Jul 23 to Jul 24
$324 total
Jul 23 - Jul 24
Total with taxes and fees
Kuanza Nature Experience
Casas dos Vimes

Casas dos Vimes

3 out of 5
Fajã dos Vimes Calheta Azores
10/10 Exceptional! (4 reviews)
"Wonderful cozy house with a fully equipped kitchen. The food supplied on our arrival was unexpected and appreciated as we arrived later than expected. Quiet, friendly community right near the ocean with trails within walking distance of the home."

Reviewed on Apr 14, 2024

Get rates
Casas dos Vimes
See all 199 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 Essential Information

Language
Portuguese
Currency
Euros
Local Welcome
Olá
Local Goodbye
Adeus
Closest Airport
Pico Island Airport (PIX)
Population
3,800
Max Temp Winter
60ºF
Max Temp Summer
70ºF
Top Sights
Igreja de Sao Jorge, Fajãs das Lagoas de Santo Cristo e dos Cubres de São Jorge and Velas Marina

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Frequently asked questions

How much does a Calheta vacation package cost?
Offering excellent value package deals from $941 on Expedia, you'll be thrilled with how little a vacation to Calheta costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Calheta?
You can generally find lower prices and greater availability in November, December and January. Check out our cheap Calheta vacation packages and you could land some great off-season deals.
How many days is enough for Calheta?
The ideal length for your Calheta vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to go to all the main sights and explore some hidden treasures along the way.
How to find the best Calheta package deals?
Use Expedia's handy filters to find some terrific Calheta package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Calheta package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Calheta vacation as a package?
You can enjoy significant savings on your Calheta retreat by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Calheta?
If you have your Calheta travel dates locked in, book as soon as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for traveling on a whim.
How to plan a trip to Calheta?

  1. Pick your travel dates: The things you plan to do in Calheta and your favorite season can help you decide when to get away.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Calheta.
  3. Organize your Calheta escape with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Calheta together.
  4. Determine how many days away: Start by listing all the attractions you'd like to experience in Calheta. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Calheta vacation package for you.
  6. Book experiences or activities in advance: Whether it's entrance to a major attraction or a day trip, you won't have to worry about missing out on the highlights of Calheta. Find all the incredible things to do in Calheta with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Calheta vacation packages?
If you're anything like us, you love traveling the world but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Calheta break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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