Emanuele Pecorari told The Press thieves had struck at Ciao in Museum Gardens, which he co-owns with his wife Sophie, four times in one week.
The 42-year-old said the coffee kiosk was targeted on September 3, 5, 7 and 8 when the gardens were closed, in addition to a separate break-in two months before.
“We feel very vulnerable,” he said from outside the kiosk where a joiner was working to repair the damage.
A North Yorkshire Police spokesperson said its investigation into the incidents is ongoing and urged anyone with information to get in touch.
Mr Pecorari said about £200 worth of items have been stolen but more money has had to be spent on repairing the damage.
On September 3, he explained, notes were taken from the till and two days later coins and a card machine were stolen, as well as the till which gardeners found “smashed” in the gardens.
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