Lake Illawarra police are investigating four break and enter incidents at The Grange Golf Club in Kembla Grange during the past two weeks.
The most recent break-in occurred on Friday night with the others on October 18, 22 and 16.
A police spokeswoman said a chainsaw and golf cart were stolen.
Dapto Leagues Club's, which owns the The Grange, executive officer David Hiscox said the number of attempts to break-in was "unusual".
He said CCTV footage showed more than one person trying to break into equipment sheds on the grounds before they bolted because the alarm sounded.
"As nothing appears to have been stolen from side the sheds, it would suggest it is just kids mucking around," Mr Hiscox said.
"It is probably not anything more sinister.
"Additional dead bolts have been installed on the roller doors to make it harder to get in."
He said the cart was not locked inside the shed when it was stolen.
Mr Hiscox said The Grange grounds were isolated making it an easy target however there were CCTV cameras, alarms and lighting to deter would-be thieves.
"The break-ins are disappointing and disruptive to the business as staff are getting calls at 1am to attend," he said.
"[The thieves] are wasting their time."
Mr Hiscox was not sure whether the same or different people were breaking in but he said that was now a matter for police.
Lake Illawarra forensic police have been to the site, collected CCTV footage and investigations are ongoing.
Anyone with information is urged to contact Lake Illawarra police.