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Mastering old-world hospitality with backend precision

Apr 16, 2025

131.82%

Property growth in less than 2 years

16.52%

Average Daily Rate (ADR) growth

19.11%

Revenue Per Available Listing (RevPAL) growth

5X

Overall revenue increase

Meet Red Cottage

Red Cottage started as a boutique property management company in scenic Upstate New York with 60 carefully curated properties. They quickly established a reputation amongst discerning NYC clientele seeking authentic weekend getaways. 

When Matthew Orley took leadership in 2022, he switched operational systems from Lodgix to Guesty to invigorate the company’s brand and vision of growth with a robust, malleable tech stack for back-end operations. Since then, Red Cottage has developed a strong marketing foundation and enjoyed significant portfolio growth with an additional 93 new properties across the Northeast.

  • Locations

    Hudson Valley, Hamptons, Poconos, Catskills, Connecticut

  • Joined Guesty

    2022

  • Property type

    Vacation homes catering to weekend travelers from NYC

Overcoming growth barriers, bottlenecks, and rising market demands

As they expanded across the Northeast, Red Cottage relied on new technological solutions to support growth without compromising their commitment to authentic, personalized experiences and old-world charm. 

Limited booking opportunities in a competitive local market 
Red Cottage initially depended on a strong local reputation and direct bookings. In an increasingly saturated local market, they had to widen their distribution strategy and begin listing on a variety of channels while still preserving the brand’s unique appeal. 

Outdated property management systems 
Red Cottage was initially hampered by inefficient backend operations, impacting revenue management, bookings, and guest communications. Their property management systems proved frustrating, slow, and unable to adapt to the rapidly evolving demands of their expanding operation and the dynamic short-term rental market.

Meeting market demand and guest expectations 
Red Cottage had built a strong network of local vendors to meet their guests’ needs. However, with rising demand for digital convenience and seamless service integration, managing these external partnerships became increasingly complex and time-consuming as they scaled operations.

Adapting for scale: backend proficiency and lifetime value 

A strategic approach to distribution and visibility   
Guesty’s Distribution Hub provided a crucial entry point to new customers, allowing Red Cottage to tap into the vast reach of prime distribution channels while still nurturing its direct booking avenues. Supported by Guesty’s high-level integrations, Red Cottage effortlessly tracked reservation opportunities from diverse sources and captured new leads, driving significant portfolio growth.

“The platform’s CRM and lead management features consistently helped convert first-time guests into loyal customers. Guesty gives us the highest quality website and direct booking engine in the industry." 

Matthew Orley, CEO

Embracing innovative management solutions  
Guesty’s suite of management tools provided Red Cottage the technological efficiency required to expand its operations. Automated messages and saved replies accelerated guest communications, while Guesty’s enterprise-level revenue management tools offered sophisticated pricing and promotional strategies. Supported by a powerful backend structure, Red Cottage successfully launched a loyalty program offering local perks and discounts.

”Building our membership program is something we would not have been able to do with any other PMS.”

Matthew Orley, CEO

Anticipating guest needs with seamless integrations 
Facing increasing demand for digital convenience and the complexities of managing local vendors, Red Cottage adopted Guesty’s comprehensive Marketplace. With over 200 third-party features and a high-level API, Red Cottage easily integrated digital services to elevate guest experiences, freeing them from the intricate and time-consuming task of managing numerous individual vendor relationships. 

The impact: a scalable model for future growth    

Red Cottage’s loyalty program fostered remarkable customer retention, with over half its guests returning for multiple stays. Despite expanding to key booking channels, direct bookings still account for an enviable 50-67% of its business. The company’s success with third-party integrations proved so strong that it now exclusively selects service providers listed on Guesty’s Marketplace.

This technological foundation has fueled significant growth, with a 131.82% increase in properties, a 16.52% rise in ADR, and a 19.11% growth in RevPAL. With a commitment to personal service amplified through technological efficiency, Red Cottage has built a scalable model that preserves the genuine experiences its guests deeply value, setting them up for continued success. 

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