Bennett, 28, returns to the Seasiders from Northern Football League side Sunderland RCA.
The full-back made one appearance for Whitby Town during the pandemic affected 2020/21 season.
He will be reacquainted with manager Nathan Haslam whom Bennett worked under during his time at Bishop Auckland and Whitley Bay.
"He's a player I've worked with ever since he left Middlesbrough," Haslam said.
"I had him at Bishop Auckland and Whitley Bay, technically he's very good and has a footballing brain.
"He knows everything about me and how I work, what my expectations are, so it's an opportunity for Andre to come in and do well.
"With Soni Fergus being out for as long as he is, he's got a chance to do well and secure a deal with us."
Bennett will go into contention for Whitby Town's North Riding Senior Cup fixture away at Boro Rangers tomorrow evening.
Photo credit: Whitby Town
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