I have both series (gifts from my grandfather). English Speaking Peoples is more of a narrative than a history book, but he provides alot of details not usually found in histories (especially on Marlborough and the wars of Louis XIV). As you can tell from the title, he covers Britain, Canada, Australia, and the US as the "Anglo-Saxon" powers (Britain and her children, so to speak) that share a common language, culture, etc., and eventually banded together to defeat Germany and save the world.
The WWII series combines his personal wartime memoirs with contemporary news clippings, quotes, excerpts from meetings, and so on, and presents an Anglo-centric view (alot of focus on the period between the Fall of France and Pearl Harbor, when Britain stood alone). So instead of a "history", its more of a firsthand account of WWII from someone who was intimately involved. For example, in addition to the usual "Prince of Wales and Repulse were sunk by the Japanese", you also get his reaction when he was woken by a phone call reporting the disaster. He describes the despair that set in as he realized what it meant; that with Pearl Harbor (Dec. 7) and now this (Dec. 10), the Japanese reigned uncontested over the entire expanse of waters between India and the US, without a single Allied capital ship to oppose them, which in turn meant that every single one of Britain's Far East colonies would fall. Needless to say, its very personal and emotional. All his wranglings with Stalin, the French, and his own generals, his relationship with Roosevelt, and so on.
If you like Churchill, you'll like his books. They're just like his speeches; long-winded, but eloquent and inspirational.