Is this their first winter they are living in the house? 

If you need to protect the house and cut costs, you can hire a licensed, insured plumber to winterize it.Maybe you already know this, but it took me about 10 minutes to even find it listed for rent.

If you're doing this during the winter months -- when Airbnb occupancy would already be super low -- you're likely getting for a medium-term rental what you would have gotten on Airbnb anyway.I'm leery of Westminster for the moment.

Had a quarter-life crisis and decided to needed to get out of the Chicago winters. 

Heating costs go up in winter, as does electric due to the reduced natural light and people being indoors more.

Imagine tax break, winter break and restriction break, who doesn't want that when you can have it all thanks to hybrid working.

My Dad works at Timberline a few weekends during the winter, so it would make sense for him to have somewhere to stay during his shifts.

One of the pools was uprooted from the winter freeze.

., etc.)Second, traditionally (when the market is "normal"), summer tends to be the worst time to buy, and the best time to sell because demand usually peaks in the summer months, and demand usually slows in the winter (especially around the holidays).

I had a STR rental and we just booked 30-day stays, mostly to Canadians and winter visitors from Chicago and New York.