@Jennie170 it sounds like you need a local co-host who is familiar with your house and what needs to be done to winterize it between guests. Smart systems aside, there are always things to be checked on and monitored during the winter, particularly if you get a really cold snap.
I'm in a bit of a similar situation, and I don't think I'd rest easy unless I knew with certainty that the systems for my house had been shut down or adjusted properly.
I spent the time and effort to have the pipes at my cabin wrapped with heat tape (it's small, so just a run from the basement to the kitchen and bathroom), and I have no central heat, so I keep the heat at a bare minimum (50 degrees) between guests.
My own little house on the same property has no heat other than a wood stove, so I have to drain the water from the plumbing system when I leave in the winter. It's not rocket science, but I don't know that I'd trust guests to do something like that, nor would I ask them to.
A local co-host can handle all this for you, check on the place during or after a big storm or cold snap, and prepare for incoming guests. Yes, it will cost money, but it's entirely worth it to alleviate the worry and also to provide a great guest experience.
I'm assuming that you'll need someone anyway since it's not your primary residence and it seems to be some distance from your home.
Absolutely make it worth your while by charging enough to justify opening, shutting down, and cleaning the house.
Cold snaps are always a bit nerve wracking for me, but I'm lucky enough to either be on the property or have someone check on things when that happens.
I have yet to find a competent co-host, but I'm ever hopeful.......
Good luck, Kia