Classic Cottages Brand Guidelines: The Cornish Agency Begun With Two Porthleven Cottages

A couple, a fishing village and a portfolio that grew.

Classic Cottages dates itself to 1977. The company says that Tony and Clare Tregoning, who had decided to settle in the South West, began the business with two run-down fishermen’s cottages in Porthleven, on the south coast of west Cornwall, and turned them into holiday homes they would want to stay in themselves. As word spread in the village, it says, other local owners asked them to take on their cottages too, and the couple soon had about 25 properties to fill.

That was the turn from owners to agents. By the company’s account, the systems they had built for bookings, payments and arrivals could handle many more homes, so the emphasis moved to the agency side. In 1986 it expanded beyond Cornwall into Devon, Somerset and Dorset, and the business, until then called Cornish Cottages, took the name Classic Cottages. Companies House lists Classic Cottages Limited as incorporated in November 1985 and still active.

The company says it had 250 cottages on its books by the end of the 1980s, administered on a single ICL computer about a metre square, and that the founders’ son, Simon, joined as a partner in that period. It puts its portfolio at about 700 properties by the end of the 1990s, and it marks a visit by the Princess Royal in 1999 as one of the landmarks of that decade, telling with some humour how Tony declined to part with a new Apple Macintosh computer that caught the royal visitor’s eye.

Regional offices and a group behind them.

The 2000s and 2010s brought new places and new people, as the company tells it. In 2007 the founders’ daughter Kate joined, bringing design experience, and the company says the Classic brand was refreshed across all its touchpoints, winning awards for its website and brochure; it does not name them. In 2015 it took on a collection of cottages on the Roseland peninsula and opened an office there; in 2017 it moved onto the Isle of Wight, teaming up with a local agent and opening a high-street office at Seaview; and in 2018 it opened regional offices at Bridport in Dorset and Battle in Sussex.

Growth also came by acquisition. In July 2024 TheBusinessDesk.com reported that Classic Cottages had bought Norfolk Holiday Homes, adding 30 properties and keeping that agency’s office at Hunstanton on the north Norfolk coast and appointing a local property manager and assistant to run the portfolio; the report put Classic’s portfolio at 1,462 letting properties across the UK. The company’s own website now says it offers more than 1,600 holiday cottages and employs more than 50 people.

Behind the brand sits a group. The company says the founding family and its chairman created Sapphire Holidays as a holding company, a step it dates to 2021, and Companies House lists Sapphire Holidays Limited as the controlling shareholder of Classic Cottages Limited. In September 2024 TheBusinessDesk.com described Sapphire as a family-owned group of self-catering letting agencies including Aspects Holidays, Boutique Retreats, Classic Cottages and Unique Hideaways, managing about 2,650 holiday properties; in January 2025 it reported that the group had bought Grandeur Property Management of Poole, which kept its own name.

Design and documentation.

Holiday cottage agencies sell places rather than products, and their pages are built around the property photograph. A typical listing opens on an exterior shot of a cottage, a cabin or a tent in its landscape, followed by interiors, the view from the door and, increasingly, the hot tub or the log burner. The companies publish these images themselves, usually taken for the agency or supplied by the owner, and the look of a brand is set as much by that photography as by any logo.

Naming follows the way people plan a break. Agency menus are organised by region (the Lake District, Cornwall, the Scottish Highlands, North Wales) and by collection: dog-friendly cottages, cottages with a hot tub, coastal cottages, large houses for groups, last-minute breaks. Sykes Holiday Cottages, for example, lists collections of this kind alongside its region pages, and glamping and campsite platforms apply the same logic to shepherd’s huts, yurts, treehouses and pitches.

Search is the core interface. Guests enter a place, dates and party size, then filter by features and browse results as a list or on a map. Some groups now add conversational search: in February 2026 Awaze said it had launched an app within ChatGPT that starts with Cottages.com and returns live availability from a plain-language request.

Behind the consumer brands sits a second audience: property owners. Most agencies run separate pages that invite owners to let their home through them, and corporate sites describe group structures. Several of the names in this guide belong to larger groups: Cottages.com to Awaze, and Sykes Holiday Cottages to Forge Holiday Group, the parent brand Sykes launched in 2023. This guide sets out who founded each brand, who owns it, and what it publishes, and marks what rests only on the company’s own word.

From a Georgian house in Helston to Onyx House in Hayle.

The company’s offices tell the story of its scale. For many years it worked from a Georgian house in Helston; in the summer of 2020, it says, it moved to a new head office in Hayle, the building later known as Sapphire House. In November 2025 the Voice newspapers in Cornwall reported that Sapphire Holidays had opened a second building nearby, Onyx House on Hayle Business Park, a former industrial building repurposed as offices. According to that report, Classic Cottages occupies its ground floor, with Boutique Retreats and Unique Hideaways on the mezzanine, while Sapphire House continues to house Aspects Holidays and the group’s shared teams. The paper said the building has a rooftop solar array with batteries, ground-source heating from six deep boreholes, rainwater harvesting and a car park planted as a wildflower meadow, and that it was designed by the Truro practice KAST Architects. It put the group’s staff at more than 205 people, after acquisitions in Dorset, North Devon and the Isle of Man during 2025, and quoted Simon Tregoning, owner and chairman of Sapphire Holidays, describing it as a long-established, family-owned group.

Classic Cottages also presents itself through environmental and community commitments. Its website says it is a certified B Corp, giving an overall B Impact score of 90.2, and lists staff volunteering days, support for local charities, solar power at its Cornish headquarters and green guides for guests and owners; it says those values go back to its beginnings in 1977. Its home page gathers properties into themed collections, such as cottages by the sea, cottages by a sandy beach, cottages that take dogs, cottages with hot tubs and a glamping selection, beside seasonal pages for short breaks, Christmas and the school summer holidays.

For a design guide, Classic Cottages shows how a family agency can keep a regional, coastal voice while a group grows behind it. Compare Original Cottages, another agency built from local brands, and Sykes Holiday Cottages. For this guide we use a harbour blue, a sand and a clay accent with a serif, an unofficial interpretation; no product or logo is reproduced.

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