CanadaStays was a Canadian online marketplace for short-term vacation rental properties, with over 250,000 cottages, cabins, chalets and condos available to rent across Canada, the US, the Caribbean, Mexico and South America.

[3] CanadaStays was founded in Toronto in 2008 by Mark Bordo under the name CottageCountry, with the aim of creating a remote rental marketplace for owners looking to rent their properties in Canada.

[8] The Globe & Mail covered the cottage rental industry in 2012, citing CottageCountry as a major player alongside other free services such as Craigslist.

The industry of vacation rentals saw a boom during this time, with sites such as CottageCountry providing a great return on investment, with "most cottages rent for at least $1,000 per week", according to The Globe and Mail.

[10] The strategy was said to expand viewers and potential bookings for its clients, with up to 2.5 million unique visitors per month viewing each listing.

In 2017, CanadaStays reported growing Canadian demand for vacation rentals after seeing a 74% increase in bookings and rising trip values over the course of the year.

[16] The company was also featured in the Daily Hive, which published a list of Canada's most in-demand vacation rental destinations based on CanadaStays' 2017 search and booking data.