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I've stayed in two:
The Waterford Inne B&B in Waterford, ME (north of Sebago Lake, south of Bethel).
Very nice inn, mostly caters to the skiers heading to Bethel. The dinner, if you choose to have it there, is delicious. There's a nice common room with a fireplace-like woodstove going where we read for hours. Historic house, country location, lovely in October - Waterford has a few B&Bs and not much else. The closest towns with restaurants is Norway & Paris and that's a bit of a drive so if you aren't skiing all day, it's a bit of a pain to go out for meals (it's a bit of a drive). Norway had a decent used book store a few years ago, don't know if it's still there.
Conroy's B&B in Lenox or Stockbridge, Massachusetts (I think it's just within the Stockbridge border).
Rooms in historic house or in the barn (there's an apartment there also - great for larger gatherings or meetups!). Very nice accommodations, breakfasts were kind of dull (if I remember correctly), plenty to see in the Berkshires. We went in late October and there was still plenty to see. Ventfort Hall (I used to live here in the 70s!), Edith Wharton's "The Mount", the Tanglewood grounds...stroll Main Street, Stockbridge...etc.