Anthony Taylor, 57, who spent some of the money on luxury hotels and goods, was also banned from being a company director.
He previously admitted an offence each of fraudulent trading, unfairly offering package holidays without security, and engaging in unfair trading relating to holidays and outings the tune of £65,985.
The defendant's Bilston-based TT Tours enterprise ceased trading in February last year leaving hundreds of mainly elderly customers stranded when the coaches failed to turn up to collect them for a break to Torquay, Devon.
Around 300 victims including pensioners' clubs lost their money.
Sentencing him at Wolverhampton Crown Court on Friday, Judge Mr Recorder Marc Brown told Taylor, of Willenhall: "In all the fraud was a prolonged and despicable deception. You raised people's hopes and ultimately leaving them out of pocket."
The judge said Taylor, who has previous convictions for fraud and theft, had managed the company in a "woeful manner" without a business account and no records of transactions.
Mr Ben Mills, prosecuting, said: "On July 7, 2019 Anthony Taylor incorporated TT Holiday Ltd. He had operated as a sole trader for a short period before that.
"No accounts have ever been filed. He based himself at Bilston Indoor Market where he ran a stall selling holidays and day trips.
"In mid 2019 he employed an assistant called Carol Bayliss. He had a brochure full of holidays with deals that were too good to be true.
"He did provide a number of holidays in the later part of 2019, but then throughout the latter half of 2019 he sold a large number of customers a variety of day trips and holidays for 2020 which he then failed to provide.
"In particular they included a cut-price five-day coach holiday to Torquay which customers were told included breakfast, a five-course evening meal, free bar between 7pm and 11pm and two excursions."
The court heard that Taylor, who had gambling issues, had convictions dating to the 1980s including five for obtaining property by deception in 1995; 16 for theft, fraud, making false representation in 2007 relating to £12,000 stolen from employer which he spent on gambling resulting in him being jailed for 12 months.
He was also a convicted for shoplifting in 2018.
Mr Charles Crinion, mitigating, said: "He fully understands the seriousness of the situation and the impact it has had on son many people. He understands that it will be a prison sentence."
For fraudulent trading Taylor, of Mount Road, Portobello, Willenhall, was jailed for four years. He must serve half before being released on licence. There was no separate penalty for the commercial offences.
He was also disqualified from being a company director for 10 years for his actions.