That's planning ahead!
Seems like a good idea - Stowe will provide a good base for the area. Check out Spruce Peak at Stowe for lodging up there - will have a spa. You might also consider a couple of days in Burlington (Hotel Vermont) or Quechee (Woodstock Inn).
Lots of hotel choices in Boston and they'll be pricey in October. Should decide whether you want to be near the water, shopping or tourist sites.