Yes. Tire pressure for me seems to disproportionately decrease with big cold temperature drops. There is an engineering chart around that shows something like a 1 psi drop for every 10 degree drop BUT personally I've seen tire pressures regularly drop to about 15 psi from about 32 when the temps suddenly drop from the 40's to the low teens.
Probably has more to do with the ability of the valve stem to hold pressure under those conditions rather then the compression of the air in the tires.
Just my observations. Scientists may disagree.