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We commonly speak of samsara (often called the "cycle of birth and rebirth") as a place, the world we live in, but as with many concepts in Buddhism, what we think of as a thing can actually be thought of as a process. (For example, we might say the "self" cannot be reborn because the self is not a thing but a process.)
Thai forest monk Thanissaro Bhikkhu writes:
Samsara literally means "wandering-on." Many people think of it as the Buddhist name for the place where we currently live — the place we leave when we go to nibbana. But in the early Buddhist texts, it's the answer, not to the question, "Where are we?" but to the question, "What are we doing?" Instead of a place, it's a process: the tendency to keep creating worlds and then moving into them. As one world falls apart, you create another one and go there. At the same time, you bump into other people who are creating their own worlds, too.
The play and creativity in the process can sometimes be enjoyable. In fact, it would be perfectly innocuous if it didn't entail so much suffering. The worlds we create keep caving in and killing us. Moving into a new world requires effort: not only the pains and risks of taking birth, but also the hard knocks — mental and physical — that come from going through childhood into adulthood, over and over again. The Buddha once asked his monks, "Which do you think is greater: the water in the oceans or the tears you've shed while wandering on?" His answer: the tears. Think of that the next time you gaze at the ocean or play in its waves.
Read the entire entry on Samsara at Access to Insight.