The man is the second person to fall from the Stanley Street hotel and apartment complex in recent years.
"He was making his way from his second floor apartment towards the roof," Senior Constable Chris Blackford says.
"He fell to the car park below and suffered a major head injury. His condition is described as critical."
Police couldn't confirm the height the man fell from but the second floor is at least six metres from the car park.
In 2008, Invercargill electrician Shaun Hogan fell to his death at The Glebe after gaining access to the courtyard and climbing to the roof.
Queenstown construction worker Andy Pearson suffered chest and pelvic injuries after he slipped and fell from the third floor of The Glebe when it was being built in 2003.
In 2009, English backpacker James Smith fell about 10m to his death from the roof of Base Backpackers on Shotover Street, Queenstown.
- additional reporting Mountain Scene