When Zack and Cody want to make friends, they meet Max and Tapeworm. After the 'Drew Crew' finds out where they live, they suddenly want to hang out with the twins. London needs to higher her grades so Moseby hires Maddie to tutor her. In the meantime, Maddie develops a crush on Lance the lifeguard and asks London for advice on how to be mean because he is obsessed with water.
Zack and Cody want new bikes but can't afford them. A beauty pageant comes to the Tipton and Cody accidentally is put in it. Zack takes advantage of this and convinces him to stay in so they could use the prize money. Cody crushes on a pageant contestant, Rebecca, and wants her to win.
Moseby won't let London go out with her friends because of an article about her in the newspaper, but Moseby lets London go out with her friends because Maddy is going. Maddie and Jason find they have a lot in common with each other and start to like each other. Maddie needs Zach and Cody's help to fool Jason into thinking that she is rich.
Zach and Cody have been spending way too much money which causes them to get grounded. But when they learn a celebrity couple are holding their wedding at the Tipton and that if someone can get a picture of the kiss they get $20,000.00, Zach and Cody will have to use their sly ways to sneak in and get the picture to pay off their moms bill. Will they succeed?
Carrie receives anonymous flowers with a beautiful poem outside her door. She thinks they were sent by the concierge, but Zach and Cody don't think that he is telling their mother the truth. They set out to find their mother's real secret admirer.
Zack and Max enter a dance competition, making Cody feel that Zack is better than him at everything. When Zack hurts his ankle by jumping on the bed, Cody has to step in for him, learning to appreciate his own abilities. London lends Maddie money for her parents, but then uses Maddie's indebtedness to exploit her ruthlessly.
Maddie gets her prom to be at the Tipton after London convinces Mr. Moseby. Maddie also wants someone special to ask her to the dance. Zack, thinking that he is the one that Maddie wants to take her to the prom, shows up to the prom in a tux.
Zack and Cody enter the Battle of the Bands that is held at the Tipton. Zack and Cody have some differences about their band, so they break up the band. Once it comes down to it, they realize that they work better together that apart.
Estebon is accused of stealing from one of the guests at the Tipton, but Zack and Cody think that he is innocent. So, they set out to prove that he is innocent. London goes away on vacation, but cannot bring Ivana with her, so she had Maddie watch her. Maddie and Ivana bond, and Ivana is angry with London for leaving her.
London's father loses his fortune, so he must sell all of London's expensive things. London must move into Maddie's house until her father can find a place for her to stay. London learns what it is like to be poor, and appreciates a life that she's never had to experience.
London falls for the son of her father's enemy, who owns the St. Mark Hotel. They sneak around so they can be together and Maddie helps them. Zack takes advantage of Cody's ability to bake amazing cookies to make some money.
After London starts and rumor about Maddie dating the lifeguard, Maddie unintentionally starts a rumor about London wearing real fox fur. Cody decides that he wants to be separated from Zack and experiments with his look, but it ends up getting him into trouble when the interviewer for a contest that he entered shows up.
Mr. Moseby takes the twins to a baseball game so Carrie can get a day off, but he becomes the most hated man in Boston because he cost the Red Sox the game when he catches a ball for Cody. London sets Maddie on a date with one of her friends, but Maddie's hair will not cooperate.
When Zack and Cody's father arrives in town with his band, Zack decides that his dad is a lot more fun to be with than his mom, causing him to run away by stowing away on his dad's touring bus. Meanwhile, the boys' mom tries to make restitution for driving Zack away by forcing Cody to have non-stop fun with her.
It's Christmas. Everybody gets snowed in the hotel while a pregnant Mexican woman and her husband stays there. As there is no way for the hotel to receive any oil, Arwin has to do what he can to keep everybody warm.
Max impulsively kisses Zack after a basketball victory, causing them both to question their relationship, and the team to urge him to ask her out on a date. Maddie tries to curb London's compulsive shopping habits.
Inspired by a motivational speaker who emphasizes to people to "Be the pilot of your own life", Cody sets out on a mission to get his friends and family to pilot their own lives, throwing the cast into turmoil and chaos. Meanwhile, Maddie and London compete--no holds barred--for a Trendy Teen title.