Fire crews from Stokesley, Northallerton and Thirsk were called to the incident on the A19 at about 1pm.
Four occupants of one of the vehicles had managed to get out before firefighters arrived and were reported to have suffered only minor injuries.
A casualty in the second vehicle remained inside and firefighters removed the roof of the car to allow paramedics to assess them.
The casualty was then removed from the vehicle.
All five people involved in the collision were taken to hospital for precautionary checks.
The fire service said no serious injuries were reported.
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