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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