During this time, Finch continued to appear on stage in various productions while under contract to Olivier. Finch's closeness to the Olivier family led to an affair with Olivier's beautiful but increasingly unstable wife, Vivien Leigh, which began in 1948, and continued on and off for several years, ultimately falling apart due to her deteriorating mental condition.
Finch's next three films saw him support notable female stars: Sophia Loren in Judith (1966), Melina Mercouri in 10:30 P.M. Summer (1966) and Julie Christie in Far from the Madding Crowd (1967). He was reunited with Aldrich for The Legend of Lylah Clare (1968). The Red Tent (1970) was an expensive international adventure film, with Finch as Umberto Nobile.
Finch co-wrote and directed an award-winning short film, The Day (1960) and announced plans to direct a feature but it did not eventuate. He won his third BAFTA for Best Actor for No Love for Johnnie (1961), although like Oscar Wilde, the film lost money. He was originally chosen to play Julius Caesar in Cleopatra (1963) and filmed scenes in London, but when the film was postponed he withdrew; the role was recast with Rex Harrison.