How to Turn STR Guests Into Loyal Customers
Podcast Summary
Most short-term rental operators focus on adding more units, entering new markets, and automating their operations. But what if the strongest competitive advantage is not the size of your portfolio, but the relationship you build with your guests?
In this episode of STR Global Unlocked, I speak with Matthew Orley, CEO of Red Cottage, about how STR operators can build a memorable brand that drives guest loyalty, repeat stays, and direct bookings.
Matthew explains why many property managers do not truly own their guest relationships, how Red Cottage built a successful membership program, and why loyalty needs to offer more than simple discounts. He also shares how a clearly defined target guest, a consistent portfolio, and proactive communication can turn one-time bookings into long-term customer relationships.
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Connect with Matthew Orley on LinkedIn and learn more about how brand ownership, membership and repeat-guest loyalty, human communication as a moat against automation, and Red Cottage's guests-first model are reshaping the future of short-term rentals and hospitality.
Guest Appearing in this Episode
Matthew Orley
Matthew Orley is the CEO and owner of Red Cottage, a premium vacation rental management and hospitality brand specializing in distinctive homes across the Northeastern United States.
His relationship with Red Cottage began as a guest in 2012. Impressed by the company’s carefully curated properties, consistent service, and strong brand identity, he acquired the business in 2022. Since then, Matthew has led Red Cottage through a period of significant expansion, growing its portfolio from approximately 50 homes to more than 200 properties through organic growth and strategic acquisitions.
Drawing on his background in brand management, entrepreneurship, and hospitality, Matthew is focused on building a scalable regional platform without losing the local expertise and personal service that differentiate Red Cottage. Under his leadership, the company has introduced new concepts such as a guest membership program and expanded its presence across New York, Vermont, New Hampshire, and other key markets in the Northeast.
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