One can find many pictures to illustrate examples of the tangent bundle, eg from wiki
The simple explanation would be that, to get the tangent bundle, you collect union up the tangent spaces at each point of the circle. Simple, intuitive and straight to the point.
But, how does the cotangent space looks like? If not a picture, could some geometric intuition for it be provided?
I couldn't find any good sources on this after searching :/

Each red line in the picture represents what we call the fiber of a bundle. There is exactly one for each point in the base manifold (depicted as the blue circle), commonly denoted $M$.
Each type of bundle has a specific type of fiber. The tangent bundle fiber at $p\in M$ is called the tangent space at $p$ and denoted $T_pM$. This is defined rigorously in all the standard textbooks on manifolds or differential geometry. For example, it can be viewed as the space of all possible velocity vectors at $p$ of curves passing through $p$.
From here, it’s linear algebra. $T_pM$ turns out to be a vector space. There are other vector spaces naturally associated to a vector space $V$. The most important is the dual vector space $V^*$. The cotangent bundle is the bundle whose fiber at $p$ is the dual vector space of $T_pM$, denoted $T^*M$.