There are a lot of Airbnb listings for places like Cannon, Waterville, etc. It’s so common to rent out houses and condos in these ski resort areas that you’ll find a lot of realtors that can walk you through the process and give you ideas of what is involved. I’m not sure where you are in MA but I’d really do NH over VT. While they seem pretty equally close VT is a lot more geographically isolated in that it’s harder to get from here (wherever in VT) to there (wherever in VT). I love the Whites and really wanted a place up there but ultimately decided it was a pipe dream. One thing I’d consider is _when_ would you want to use it. There are times that are particularly popular for rentals, like Columbus Day, February break, etc. and those are the times you’d be most assured renters, but also most likely to want to use it yourself. We know people who live in Newton and rent their cape house for the summer weeks except maybe one or two. They only really use it for themselves in the off season as they can get so much more renting it per week over the summer. When you’d want to use vs. rent will make a difference in the economics. Some of these areas have more amenities that make them nice year round but not sure how full the ski villages are in the non-ski season.
momma to DD 12/08 & DS 3/13