You just have to lower your prices. My summer bookings tend to be much shorter stays, anywhere from 1-4 nights usually. In winter I've found that I have to reduce prices by a good 30-40% from what I charge in summer, and I tend to get more people who need a place for a week+. I don't do long term bookings - my max is 10 days - but if you do, it will probably be easier to keep your calendar full. There are a lot of visiting students who only need a place for a month or for one semester who don't want to/can't sign a lease for that reason. In the winter I get a lot of business travelers, Amazon interviewees, apartment/house hunters, convention attendees, students traveling for fall/winter/spring break, etc. My calendar usually stays pretty full in the off-season, but I'm obviously making a lot less money due to off-season pricing.