Last winter I drove to Vermont, and passed by this cute property, the Sylvanus Lodge . It's in Hillsdale, NY, but it's pretty much in the Berkshires area. I didn't go inside, but from looking at the pictures, and seeing how reasonable it is ($80-$125 in peak season), I think it's worth giving it a try. The studio apartment is really the only option for families, and it can sleep up to five.
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