Family Friends, based in Imperial Road, was awarded £13,230.
The money will go towards funding two part-time family support workers who will provide one-to-one support to members of the Armed Forces community and their families.
Daniel Elser, from the Royal British Legion, said: “Armed Forces families are often faced with challenges such as frequent relocation and long periods of separation which can be very difficult to deal with, and may lead to problems such as anxiety and stress.
“We are proud to work with Family Friends, which will make a real, long-lasting, difference to children and families in the Windsor and Maidenhead area.”
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The Met Office has issued a yellow alert for Windsor and Maidenhead, Slough and Wokingham, warning that rain moving eastwards across the south of the country may turn to snow in some places.