Building a Design-Driven STR Portfolio with Red Cottage CEO Matthew Orley

In this episode of STR Data Lab, Jamie sits down with Matthew Orley, CEO of Red Cottage, to explore the company’s unique approach to short-term rentals. Matthew shares the story behind Red Cottage, which he acquired two years ago, and explains its focus on design-centric homes in the Catskills and Hudson Valley regions. Red Cottage primarily caters to weekend travelers from New York City, Boston, and Philadelphia, with an emphasis on aesthetically appealing properties across various price points.

Matthew highlights how Red Cottage provides unique value to homeowners by attracting a distinct clientele and curating listings that stand out in the competitive short-term rental market. He also touches on their impressive direct booking rate and the recent launch of a membership program offering exclusive perks like discounted rates, waived fees, concierge services, and early access to new properties.

He explains how the steady demand for weekend getaways in their market helps them manage lower seasonality compared to other vacation destinations. Matthew also reflects on the impact of COVID-19, noting the initial surge in demand followed by market normalization. To stay competitive, he emphasizes the importance of adopting new software, leveraging technology, and building strong partnerships.

Matthew also dives into the operational challenges of property management, stressing the need for scalable systems and efficient information management. He wraps up by discussing the future of the property management industry, predicting continued consolidation and professionalization as a response to rising operational costs and the increasing need for advanced tech solutions.

You don’t want to miss this episode!

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https://www.linkedin.com/in/mattheworley

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Episode 98