A very friendly but accident-prone octopus checks into the Furchester Hotel. As soon as Olivia the Octopus sets foot in the hotel, she starts knocking things and people over. Cookie Monster is announcing the soon-to-be-famous Furchester Cookie Tower, but Olivia cannot keep track of her arms and sends the tower flying. Elmo and Phoebe put their furry heads together and think of a way to help Olivia keep track of her arms so she won't keep knocking things over.

The Furchester Hotel's Monster Babysitting Service is in full swing, and they are looking after a baby monster called Adrianna. Adrianna is supercute and loves to crawl about everywhere. Her parents can never manage to get her to fall asleep, so they ask if the Furchesters know any tricks for getting a baby monster to sleep. Suddenly all the guests are giving suggestions on how to get Adrianna to fall asleep.