I have a rental house in Gilford on Winnipesaukee. I have been renting it out since 2003 using this site and Craigslist for advertising. It is always full in the summer when it is rented weekly, and I have had good luck finding one renter for October 1, through Memorial Day every year. The winter monthly rate is less than half of the summer weekly rate. The vast majority of the renters have been decent and respectful and the problems have been minimal. At this point over half of the summer renters come back every year so there are not that many weeks to fill.
One thing (and I may be wrong about this) is with a rental property your real estate taxes become a business expense. It is my belief that, despite the new limitation on the real estate tax deduction, you may be able to deduct beyond that limit depending upon the percentage of time you use the house. I would certainly check with an accountant.
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