A succah in Jerusalem
When asked what the real significance of the Biblical injuction of dwelling in the Succah for seven days is about, Rabbi Eliezer in the Talmud stated it referred to the Clouds of glory that protected the Children of Israel in the wilderness; Rabbi Akiva stated it referred to the physical structure itself.
Rabbi Ashlag, in a letter writing, his students on Succot asks how was it that two such great Sages came up with such very different ideas? He explains that they are both looking at the succah as representing faith in God but one is looking at the light of faith and the other at the creation of the actual vehicle for this great light. Faith is the vehicle with whihc we may connect with God both in times of God’s light being revealed to us and in times when it is hidden from us.
The festival of succot gives us an opportunity to build our refuge of faith for the entire coming year.
From a letter by Rabbi Baruch Shalom Ashlag
The children of Israel were given three gifts to protect them through the travails of the wilderness. Manna from heaven, Miriam’s well and the clouds of Glory. The clouds of Glory have the same essence of that of Aaron the priest, chesed the Sephirah of loving-kindness, and this is the same light we attract to ourselves when we sit in the Succah. The roof of the Succah symbolizes the shelter of faith . Sitting under its shelter gives us faith for the New Year now open to us . Listen to full talk, 8 minutes)
The Zohar teaches us that three gifts were given to the Children of Israel when travelling through the wilderness. One of them was the clouds of glory which led them and protected them from the heat of the sun and hid them from unfriendly eyes. Their essence is the same as that of the succah. Listen to full talk http://www.nehorapress.com/115470/audio-on-festivals