There is a relatively cheap Econo Lodge in Brattleboro, VT close to a large grocery store and a restaurant or two, but you will have to climb a hill to get there. I've ridden VT/MA 142 south from Brattleboro then some other roads to Deerfield, MA. 142 is pretty low traffic in the morning. Most of the vehicles are heading towards the Brattleboro area.
BTW...I would map out both sides carefully if you goal is to avoid as many hills as possible. I would also use Street View to check for shoulders.
Last edited by indyfabz; 04-11-19 at 04:41 AM.