Calheta Vacations from $903

Book a Hotel + Flight or Car together to unlock savings

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 d'Avó Guesthouse

Casa d'Avó Guesthouse

3 out of 5
Price was $934, price is now $903 per person
$903
per person
Sep 26 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
9.8/10 Exceptional! (45 reviews)
Ben arredata; pulitissima e personale gentilissimo

Reviewed on Aug 7, 2025

Quinta da Magnólia

Quinta da Magnólia

3 out of 5
Price was $1,270, price is now $1,170 per person
$1,170
per person
Oct 11 - Oct 15
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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

Quinta do Almanac

Quinta do Almanac

2 out of 5
Price was $1,218, price is now $1,139 per person
$1,139
per person
Sep 26 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
No reviews
Cabanas da Viscondessa

Cabanas da Viscondessa

3.5 out of 5
Price was $1,254, price is now $1,179 per person
$1,179
per person
Sep 26 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
10/10 Exceptional! (9 reviews)
Setting was peaceful, easy parking, restaurant was wonderful. Jorge and the staff in the restaurant were very helpful and very nice

Reviewed on Jun 13, 2025

Kuanza Nature Experience

Kuanza Nature Experience

4 out of 5
Price was $1,222, price is now $1,186 per person
$1,186
per person
Sep 26 - Sep 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sao Jorge Island (SJZ)
10/10 Exceptional! (6 reviews)
This property is in a spectacular location overlooking the magnificent Atlantic Ocean. You have to coordinate the resorts ATV transportation but it's we'll with the effort. This is a perfect place to escape so stay at least a few days if not more. You should stop at the grocery store and be fully stocked for meals although you're greeted with homemade bread, local cheese and the owners produced wine.

Reviewed on Apr 28, 2025

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

Calheta Hotel Deals

Azores Youth Hostels - São Jorge

Azores Youth Hostels - São Jorge

2 out of 5
Canada da Vinha Nova, Fajã Grande, Calheta
$45 nightly
The price is $52 total per night from Sep 3 to Sep 4
$52 total
Sep 3 - Sep 4
Total with taxes and fees
8.2/10 Very Good! (20 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
$223 nightly
The price is $237 total per night from Sep 15 to Sep 16
$237 total
Sep 15 - Sep 16
Total with taxes and fees
10/10 Exceptional! (6 reviews)
"This property is in a spectacular location overlooking the magnificent Atlantic Ocean. You have to coordinate the resorts ATV transportation but it's we'll with the effort. This is a perfect place to escape so stay at least a few days if not more. You should stop at the grocery store and be fully ..."

Reviewed on Apr 28, 2025

Kuanza Nature Experience
Matilde's House, in the paradise Fajã de São João

Matilde's House, in the paradise Fajã de São João

Santo Antão, São Jorge
9.4/10 Exceptional! (3 reviews)
Sehr schöne 3 Tage
"Haus ist etwas dunkel, aber ansonsten sehr gut eingerichtet und sauber. Blick von der Terrasse aufs Meer und auf die Insel Pico. Wer Katzen mag, ist hier sehr gut aufgehoben."

Reviewed on May 30, 2025

Get rates
Matilde's House, in the paradise Fajã de São João
See all 237 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Calheta vacation package cost?
Offering excellent value package deals from $903 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.