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Driving conditions from Denver to Winter Park

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Two questions:

1) We are on a bit of a budget and have found a reasonable hotel in Winter Park for $150 per night but Denver has a Marriott for $80 per night. Would you suggest doubling your expenses for the convenience of staying in Winter Park?

2) How are the driving conditions between Denver and Winter Park? We are from the flatlands where the sun shines 365 .... are we ok in a rental car?

THanks

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