The Evangelical Stance - Many evangelicals will condemn repetitive prayers (to say nothing of who the Rosary is seemingly built around) because of Matthew 6:7 which states, "But when ye pray, use not vain repetitions, as the heathen do: for they think that they shall be heard for their much speaking."
The Counter Argument - The first question that must be asked is, was Jesus ever in the habit of condemning Himself? A strange question with a very obvious answer - No. Absolutely not. So why ask this question in the first place? Because Jesus, for all his Messianic-ship, was a devoted Jew who devotedly followed the Jewish customs. One of these being, meditating upon the Psalms daily - in particular, Psalm 136. There's probably not a more repetitious prayer-Psalm in the entire Bible - 26 times we read, "for his mercy endureth for ever", "O give thanks" 4 times, and the "To Him" exhortation 8 times. As a devoutly practicing Jew, Jesus would have prayed through the Psalm on a weekly, if not daily basis. Even when faced with his certain death, Christ prays in the Garden of Gethsemane in a repetitive fashion, as is noted in Matthew 26:39-44 where he prays to his Father to "let this cup pass" 3 times. So is Jesus condemning something He Himself does?
In heaven, we are told in Revelations 4:8 that the angels rejoice in prayer without ceasing three words - " Holy, Holy, Holy". It is important to note that these can be identified as the exact same angels who repeated this exhortation to Isaiah - identifying this repetitive exhortation had been going on incessantly since at least the time of Isaiah up until the writing of Revelation, some 700 years. There is little doubt that their repetitive exhortation of prayer stopped after Revelation - so it can be safely surmised that it continues to this day and will continue in the future. Would Jesus condemn his own perfect kingdom and angels in heaven for thousands of years of praying this repetitive exhortation? No. Of course not. There's more to this story ...
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So what then is Matthew 6:7 talking about? To start with, the best translation of this verse is NOT the King James Version because in it's translation (it was used in the beginning because it is the standard translation many Evangelicals turn to), it looses the meaning of the original words used in Matthew's writings. A closer translation to Matthew's original words can be found using the NIV or ESV (to name only a couple) that translate the original more specifically using the words "babbling" and "empty phrases". Why is this distinction important? Because in the culture of the Gentiles of this time in history, their daily life and conduct had no connection to their sacrificial systems and prayer lives. This is why Matthew uses the choice words that is most accurately translated as "babbling" or "empty phrases" and not "repetitious prayer". The 'prayers' of Gentiles were traditionally a jumble of words which we void of meaning, value, truth, and love.
To make the distinction even more concrete, Matthew 15:7-9 says, "This people honors me with their lips, but their heart is far from me; in vain do they worship me, teaching as doctrines the commandments of men." To put it more succinctly, if there's honor with your speech but not your heart, then your worship doesn't matter and is in vain. Christ is not condemning repetitious prayer (obviously not or He would be guilty of what He Himself was condemning) but babbling, empty prayer that is empty and devoid of love, worship, and truth that comes from the heart of a person in love with their Creator. 
That is why repetitive prayers like the Rosary and Jesus Prayer must be animated with and by love alone. We are called to meditate on God's word night and day and these types of repetitious prayers provide us with an option do just that on a convenient rope. Every single phrase in these repetitious prayers have their birth and creation rooted in the words in Holy Scripture and the love that springs from them. And this is where all our prayer lives should originate from - repetitive or not. And I'm not just babbling about that, either.
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