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Questions About Winter Trip (especially where to stay) in Maine

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Hello! I'm in the process of planning a very last minute quick trip to Maine (from Boston) with my mom. I have a couple of questions that I was hoping to get other peoples' opinions on:

First, neither of us has ever driven in snow before (I live in Boston so I'm familiar with it, just haven't driven in it) -- if we stick with coastal destinations, do you think this will be a problem (late February)?

Also, we aren't sure where to stay -- we're looking for somewhere reasonably nice, maybe cabins, but would prefer something larger than just a B&B, perhaps a resort or something along those lines -- budgetwise, we'd aim for under $200 a night but would consider more if it were especially nice. An indoor pool would be great, but not necessary. After looking around on google, we came across Point Lookout, which seems promising, but were hoping to get opinions from others if there was anything they'd recommend.

Thanks so much for your help with this, it's very much appreciated.

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