Answer: First of all, I prefer to call the holidays you are referring to Biblical holidays. I think they were put in scripture for everyone. They certainly do not bring us salvation but they can give us a deeper spiritual life as we celebrate them and study their meaning for us. Yes, Jesus/Yeshua celebrated the holidays.
In Luke 22:7-8 Jesus discussed with his disciples preparing for Passover. In Luke 22:14-15 he talked more about Passover.
Jesus directed his disciples in Acts 1:4, Acts 2:1-4 to not leave Jerusalem but to wait for the promise of the Father. He knew this would be the time that everyone would be in Jerusalem for Shavuot/Pentecost.
In John 7 Jesus discussed going up to Jerusalem for the Feast of Tabernacles. He debated not going but later he went.
John 10:22-23 talks about the feast of dedication. If you look at the passage in Hebrew it is called Chanukkah.
When you consider the Biblical feasts and whether you should celebrate them let Jesus/Yeshua set the example.