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Recently come back from this year's double-header. Flight to Toronto; day in Niagra and over the border to Buffalo; day in Letchworth State Park and drive to Ithaca; 3 days at Watkins Glen; drive back to Toronto; several days sightseeing; 3 days at Mosport; fly back from Toronto. If I was to do it again I'd probably add a few extra days in the US to enjoy the scenery and a few days less in Toronto.
All the guides I read said to tell the rental car company you are going across the border as immigration will check the rental agreement. My experience was that nothing was checked and no-one cared. Took about half an hour waiting in the office to get into the USA, and about 30 seconds getting back into Canada.
As far as accommodation goes, I wanted something close to a few bars/restaurants rather than a B&B in the middle of nowhere. Ithaca is about half hour drive to Watkins Glen. Toronto traffic is pretty awful so stay on the east side of town. Took about an hour to get to Mosport.
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