That's a tough one without seeing the place and knowing the specifics. Your best bet would be to go to one of the big rental sites like cyberrentals.com or homeaway.com and see what other similar properties are renting for. In general, weeks into the fall and over holidays (Thanksgiving, New Years, Valentines) can be decent rental weeks. You may be able to get half or more of summer rates for some of those weeks. In general, winter month demand is pretty low for rentals. Things that help rent your place in the winter include water views, fireplaces and short walks to town. One other option is to look for an off season renter to rent your place for the off season if you have no plans to use it. You may not get as much money but you have the benefit of someone watching your place over the winter and paying the utilities.