Recommendations for outdoor temperature sensor

How cold?

Any battery powered device is going to have difficulty once you go below freezing for a prolonged period, although some do better than others.

Cao Gadget Kumo Wireless Sensor Tags are exceptionally weatherproof, but will require that you also buy one of their ethernet bridges for each 40 tags.

There are a number of community members using them.

You can either get integration through IFTTT or through a community created service manager:

Or

There are some other options as well, but I think those handle the widest range of temperature variation.

But again, it depends on the exact conditions. Are we talking about a Minnesota winter?