Complex sentence: In October 1644, he joined with Prince Rupert to attempt to re-occupy the headland at Beachley which had been taken by Massey's Parliamentarians; the attempt failed, and Winter escaped by scrambling down a cliff at Sedbury into a waiting boat.
Split into simpler sentences: In October 1644, he joined with Prince Rupert to attempt to re-occupy the headland at Beachley which had been taken by Massey's Parliamentarians. The attempt failed, and Winter escaped by scrambling down a cliff at Sedbury into a waiting boat.