Our Journey
North Yorkshire Cottage Holidays’ journey began in 2020 following the launch of our very own successful holiday cottage in the heart of Pickering, North Yorkshire. We are very much a family-run business with a great partnership between Matt and Lisa.
We began our exciting journey of managing other people’s holiday homes in 2022, with our main goal of offering a cross section of properties across our beautiful county of North Yorkshire, ensuring a personal service to both owners and guests.
In August 2025, we opened our first office in the beautiful North Yorkshire market town of Helmsley. A very exciting venture and an opportunity for us to be more visible, approachable, and showcase all our stunning properties across the wider community.
3 Meeting House Court, Helmsley, YO62 5DW
01439 788649
Our personal approach to property management
We handle all aspects of the process, from marketing and reservation management to housekeeping and maintenance, ensuring a seamless and enjoyable experience for both property owners and guests.
We recognise that each property is unique and work closely with owners to tailor our services to their specific needs and preferences. We take pride in our attention to detail and commitment to quality, striving to exceed expectations and provide an unforgettable holiday experience.
Meet the Team
Matt Cressey – Founder / Partner
Matt has lived in North Yorkshire all his life, so his knowledge of the area is extensive. Before setting up North Yorkshire Cottage Holidays, Matt worked for many years as General Manager for a local Luxury Holiday Lodge Company. He brings an abundance of experience within the tourism and hospitality industry, having a wealth of knowledge and invaluable customer service skills.
In his personal time, you will find Matt walking his beloved Labradors and also fulfilling his passion for both shooting and beating at Duncombe Park Estate in Helmsley.
[email protected] / 07796 040606
Lisa Harrison-Cressey – Founder / Partner
Lisa was also born and bred in North Yorkshire. Having successfully managed other people’s holidays homes and housekeeping services for several years, she has a keen eye for detail and vast knowledge and understanding within this area of holiday property letting. Before setting up North Yorkshire Cottage Holidays, Lisa previously worked for 25 years in the NHS in a diagnostic and management capacity, gaining valuable transferable managerial and service development skills.
In her personal time, Lisa enjoys nothing more than spending time with her family.
[email protected] / 07547 113976
Arthur, Albert & Vincent – The office Dogs
Arthur, Albert, and Vincent love spending their days in NYCH HQ, specialising in many a distraction and patrolling the office for any unwanted persons!!
In their personal time, Arthur and Albert are keen to sniff out a pheasant or two, assisting Matt beat! Vincent much prefers to stay home, snuggled around the office fire.
We would be lost without their commitment and enthusiasm in NYCH HQ!
“Together we feel we can fill a gap in the existing local market with our varied and extensive knowledge of holiday home letting, making North Yorkshire Cottage Holidays the perfect choice for potential holiday home owners!”
Born and bred in North Yorkshire, both Matt and Lisa know the area very well and can offer guests an abundance of knowledge, including areas of interest and places to visit, and all the hidden gems that North Yorkshire has to offer.
Whether you plan to visit as a guest in one of our lovely properties or you are a holiday homeowner yourself, we very much look forward to hearing from you.
Matthew Cressey & Lisa Harrison-Cressey