I often get asked, "When is the best time to buy a cottage or sell at cottage?" and the answer really will vary depending on the needs of the asker.
Traditionally prices in the spring generally are a bit higher but that's also when you will see the greatest selection of properties. You are also likely to face more competition from other buyers. After a long, cold, snowy winter people naturally start dreaming of long, lazy summer afternoons at the beach or on the deck of their own private getaway, and so the shopping begins. Depending on the winter and how long it lasts, the spring buying season generally starts in March and April. It can be a bit of a free for all as the seller compete with all the other listings and the buyers compete with all the other people looking for their piece of paradise.
Please note: This is a generality. The reality is very economy and market driven! This year, our spring listings and buyers were in short supply. Our recreational market didn't really start until July and it's still lagging quite a bit behind the previous two years.
But....there is a lot to be said for purchasing at the end of the summer too, especially if you don't mind putting a bit of work or money into your new cottage. Sellers may be more willing to negotiate a bit, in order to not have to carry the property through the winter AND the bonus to the buyer is that if you DO choose to do some work to your new piece of paradise, you can do it when the balmy breezes aren't beaconing. Additionally, you may find that tradespeople are easier to book as they look for jobs to carry them through the slow season.
While winter sales aren't common as sellers remove their properties from the market so as to not have to keep up with the snow, some wise ones keep their properties on and do sell when there is less competition. If you are going to purchase in the winter, be aware that home inspectors will be limited in what they can discover as foundations and roofs may be covered in snow. If you've been watching a property and are confident you know what you are buying, it can be a very good time to negotiate.
As you can see, there is no "best time". Each season has it's risks and benefits - it all depends on your needs and wants.