The driver of the van was taken by ambulance to Royal Shrewsbury Hospital
The accident on the A49 at Woofferton at around 1.20pm saw the road closed between the A456 and A4117 near Ludlow and a diversion in place.
West Midlands Ambulance Service said it was called to the scene at 1.13pm.
A spokesman said two ambulances, a paramedic and the Midlands Air Ambulance from Strensham attended.
The drivers of both cars were injured, and the driver of the van was seriously injured.
A West Midlands Ambulance Service spokesman said: “The driver of the van, a man, was outside the vehicle when crews arrived and was found to have suffered serious injuries.
“He was treated at the scene before being transported by blue light ground ambulance to Royal Shrewsbury Hospital for further trauma care.
“The driver of the lorry, a man, was treated at the scene for minor injuries and taken to Hereford Hospital for further checks.”
West Mercia Police said officers were called to a crash near Ashford Bowdler at around 1.20pm and closed the road.
A spokesman said one of the drivers suffered a “serious but non-life-changing injury”.
Highways England said diversions were in place in both directions until the road reopened at around 5.30pm.
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