Two Mercedes and a VW Golf were involved in the crash on Winkfield Road, Windsor, near the Legoland roundabout, late on Sunday night.
A 23-year-old man from Slough was declared dead at the scene. A 50-year-old man from Bracknell died later in hospital.
Three other people were taken to hospital.
Thames Valley Police said the next of kin of both men had been informed.
Investigations manager Richard Thorpe said: "We are investigating this tragic incident in which two men sadly lost their lives.
"We would like to hear from anyone who was on Winkfield Road before or after the collision and has any information about the vehicles or the incident."
Two car drivers were killed in a crash involving three vehicles near the Legoland theme park in Berkshire.