Our story
It started with a room full of people who didn't fit
Canterra Stays grew out of a simple, frustrating gap. When the people who matter most come together — for a wedding, a big birthday, a reunion, a team on assignment — they need room to actually be together. Hotels fragment a group across floors and hallways. Most short-term rentals were never built, prepared or staffed to host ten, twelve, sixteen people well.
So the group compromises. Grandparents end up in a hotel down the road from the kids. The wedding party scatters. The reunion loses the long, lazy mornings around one kitchen table that were the whole point. We thought that was worth fixing.
Twenty years of hosting, and homes chosen since 2009
We weren't guessing at how. Our family has been in hospitality for more than twenty years — welcoming guests and looking after travellers since before "short-term rental" was a phrase anyone used — and we've been investing in Greater Toronto real estate since 2009.
Canterra Stays is where those two lives meet: homes chosen with an investor's eye, and stays run with a host's heart. When your people walk through the door, they're stepping into two decades of knowing what makes a place feel looked after.
A home that fits the occasion, and a stay that takes care of itself
We curate and professionally manage a portfolio of large private estates, family homes, executive condos and long-stay homes — every one prepared to a consistent standard, every booking supported from the first question to the final checkout.
Guests fly in from six time zones for a wedding week, a reunion, a project or a season near family. The goal is always the same: a home that fits the occasion, and a stay that quietly takes care of itself.
One housekeeping note, since travellers occasionally ask: Canterra Stays is an independent short-term rental hospitality company based in the Greater Toronto Area, Ontario, operating 13 professionally managed homes across Brampton, Mississauga and Toronto. Canterra Stays is not affiliated with Canterra Suites Hotel, an extended-stay hotel in Edmonton, Alberta — the similar names are a coincidence, and the two companies are unrelated.








