Fall 2026 Newsletter

Stronger Rates and a Positive Fall Outlook

Rates increased by 80% after the World Cup ended, as more than 8,000 temporary event listings left the market. With that additional supply gone, conditions are more favourable for our owners.

If the warmer weather we anticipate with a Super El Niño pattern materializes, it should support bookings through fall and year-end.

Premium Service with a Toronto Team

HSG continues to lead in Superhost recognition, Guest Favourite status, and average daily rate (ADR). Our portfolio has Toronto’s highest percentage of units ranked in Airbnb’s top 5%, reflecting the care behind every stay.

Guests always speak with real people based in Toronto. That local knowledge helps us resolve issues and deliver personal support. We are growing our local team to maintain the premium service our owners and guests count on.

Recognized by Airbnb as an Industry Leader

That commitment to staying ahead was reinforced recently when members of the HSG team attended the Airbnb ProHost Summit, bringing together leading professional hosting companies and Airbnb teams from across North America.

We were extremely proud that…

HSG was recognized as a Top 5 company in North America for Excellence by Airbnb

For us, that recognition is especially meaningful because it reflects the same things we focus on every day: exceptional guest experiences, strong property performance, professional operations and continually finding new ways to make our owners' properties more successful.

Your Hostaway Owner Portal

Every HSG owner has a dedicated Hostaway Owner Portal. We encourage you to make it your primary, go-to place to view activity for your units, including bookings, revenue, reservation activity, and overall property performance. Having this information in one place makes it easier to stay informed and see how your properties are performing.

Hostaway now also offers a brand-new Owner Portal feature in its mobile app, making it easier to access this information on the go. Whether you are at home or away, the portal gives you convenient visibility into your units and keeps you connected to their activity.

Protecting Your STR Allowance

We have carefully preserved STR allowance for the periods when it can deliver the most value. Most units are well positioned to welcome short-term guests through year-end, before the annual allowance resets. We will continue to manage each property’s remaining allowance as bookings come in.

Toronto STR Inspections

Toronto’s annual STR inspection is a routine requirement. In our experience, inspections take less than five minutes. We prepare both the unit and the owner, and no owner we have supported has failed an inspection.

Please work with Riham to arrange a convenient inspection time. Once your annual inspection is complete, we do not expect another routine visit that calendar year, although the City may require additional inspections.

Staying Ahead of How Guests Search — AI is everywhere!

The way guests find their next place to stay is changing quickly. In 2026, approximately 40% of travelers are now using AI as part of the travel-planning process, with tools such as ChatGPT, Gemini and AI-powered travel platforms increasingly helping guests decide where to go and where to stay.

At HSG, we believe this represents the next major evolution in online travel search — similar to the shift to mobile booking and the growth of platforms such as Airbnb.

That’s why we have been updating and optimizing our listings specifically for AI-driven searches. We are reviewing listing titles, descriptions, amenities, location information and other content to make it easier for AI platforms to understand exactly what makes each property unique and to match it with the right guest.

Our goal is simple: when a traveler asks an AI assistant for something like “a highly rated two-bedroom apartment in downtown Toronto, close to restaurants and transit,” we want HSG-managed properties positioned to appear prominently among the recommendations.

Planning Ahead for 2027

Starting in the second week of January, listings will switch to medium-term rentals (MTR), with a minimum stay of 28 nights, to protect the 2027 STR allowance. We will open the 2027 short-term booking calendar for stays beginning May 7, 2027, and set listing rates and availability over the next few months.

As an exception to our winter MTR strategy, we are opening selected STR dates in February and March for the Backstreet Boys’ Toronto residency and the PDAC conference. This will help us capture event-driven demand while continuing to manage each property’s annual STR allowance carefully.

More to Share This Winter

Our winter newsletter will share new initiatives to put your listings in front of more potential guests and increase bookings as we prepare for 2027.

Thank you for your continued trust and partnership. We look forward to a strong close to 2026. As always, our Toronto team is here to help at booking@hostservicesgroup.com.

Best regards,

Brad, Kevin, and the HSG Team