Dave Anderson has spent almost a fortnight inside the property at Ribblehead Station, having sealed the windows and doors under cover of darkness on January 22.
He was greeted by a coach-load of supporters from his hometown of Widnes in Cheshire when emerged from the cottage after noon today.
The protest, previously described as his “last stand”, is the culmination of a long-running dispute with Network Rail.
It began after he carried out work as part of the renovation of the station master’s house more than four years ago.
In a statement, The Settle and Carlisle Railway Trust said: “The Trust and its trading subsidiary, Settle & Carlisle Railway Properties Limited, are disappointed by the unlawful occupation of the Station Master’s House, which has continued to date.
“At the start of his rental period he barricaded himself in the property without authority.”
The trust said Mr Anderson “has been informed that he has opportunities” for pursuing his dispute directly.
The property on the scenic Settle and Carlisle Railway underwent a significant renovation totalling around £300,000, which was completed in April 2013.
It is now marketed as a holiday home sleeping up to four, with rates of up to £1,095 for a week.
Mr Anderson told The Yorkshire Post that his firm – DTA Construction Ltd – had worked on the project for 12 weeks.
He said he has since lodged a claim with Network Rail for more than £160,000, which he says he is owed for expenses incurred.
And last weekend other contractors attended a peaceful gathering outside the cottage, saying they too were out of pocket.
Initially, Mr Anderson was using Facebook Live to broadcast messages about his protest from inside the property.
But since phone lines were apparently disconnected last week, his only means of communication has been walkie talkie link to supporters at the nearby pub.
During one of his earlier broadcasts, Mr Anderson told how he had lost his business and been forced to sell the home he built for his family as a result.
The 52-year-old explained that he did not have the finances needed to bring a civil court case so he had decided to stage the protest.
“I’ve rented this property out,” he said. “I’m not looking to harm anybody or doing anything wrong.
“There’s no criminal damage. All I’ve done is board myself up. I’m here and I’m here to stay until this is sorted.”
The one-week lease ended on January 27 but no attempts have been made to evict Mr Anderson since then.
Network Rail has previously said it is aware of the situation but it would be inappropriate to comment until they have spoken to Mr Anderson about his concerns and established the full facts.