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I'm an American living in Canada. I was getting my residency while living in Canada and was told that I may not be let into the country if I leave before obtaining my residency. Well I did leave and came back. Before I did, I went to the border to see if I'd have any troubles. They told me no. They look for people like you! They look for Americans living in Canada and working in the US and NOT obtaining their residency in Canada. They can deny you re-entry into Canada any time they want to. But I think they look for people who are staying in Canada for a long term.
However, because it's for the summer and you own a summer cottage, thus vacationing, it may be a bit different. I'd stop at the crossing and ask the border agent.
I know Native Americans can generally come and go as they please. I'm sure there's paperwork with that, too.
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