Poly(norbornene)-based block copolymers containing either adamantane, tetraethylene glycol (TEG) monomethyl ether, or n-butyl side-chains were synthesized using ring-opening metathesis polymerization. The adamantane- and TEG-functionalized AB diblock copolymer is amphiphilic enough to form micelles in aqueous media. In contrast, the other diblock copolymer functionalized with adamantane and n-butyl groups is not amphiphilic because both side-chains are hydrophobic. Upon addition of beta-cyclodextrin, however, the hydrophobic adamantane side-chains are decorated with hydrophilic beta-cyclodextrins through host-guest interactions, affording amphiphilic AB diblock copolymers that can be self-assembled into micellar structures. The polymeric micelles obtained using the two different approaches in this study can also be disassembled through competitive host or guest molecules. The self-assembly and disassembly processes are characterized by SEM and TEM images.