Holland grew up in Bolton, Ontario. As a youth, he played in the 2004 Quebec International Pee-Wee Hockey Tournament with the Brampton Junior Battalion minor ice hockey team. After a successful minor midget season, where Holland had 119 points (59 goals and 60 assists in 60 games), he was selected in the first round, 11th overall, by the Ontario Hockey League (OHL)'s Guelph Storm in the 2007 OHL Priority Draft. His 2008–09 season caught the attention of scouts, as he earned a spot in the OHL All-Star Game, played in the Canada-Russia Challenge and participated in the 2009 CHL Top Prospects Game. He also represented Team Canada at the 2009 IIHF World U18 Championships. Heading into the 2009 NHL Entry Draft, Holland was ranked 19th by the NHL Central Scouting Bureau. The Anaheim Ducks selected Holland in the first round, 15th overall.