The Winchester is hands down a better made gun. Take a look at the stocks. Winchester has the best looking factory stocks out there. The Featherweight is a real knockout.
Winchester's controlled round feed grips more of the case. It has an adjustable trigger (important in these days of lawyer-proof factory triggers). The Winchester also has a lot of aftermarket parts and accessories available, second only to the 700.
I have heard that Ruger has pretty loose tolerances for its barrels, while recent Winchester barrels have been very good in my experience.
While Ruger's rings and bases are free, they also limit you. Want to try another brand - too bad. Want to get rings a little higher or lower - too bad.
The Winchester has a lot of other key features - coned breech, fixed ejector, field-stripable bolt, etc. Ruger may also have these, I am not sure.
There is no doubt that the Ruger is more reasonably priced, but this is one of those instances of you definately get what you pay for. Anyway, Gart's Sports has Model 70s on sale right now for $429, which is only a few bucks more than the usual sale price for a Ruger in my area ($400).