The title is a question I have been asked occasionally, and one I’ve pondered far more frequently. It is a peculiarly beautiful and beautifully peculiar place to live.
This town, home to Legoland, countless monarchs, Eton College, and some more monarchs still, became my temporary residence in the six weeks prior to Christmas. Working at Heathrow’s Terminal 5, I desired accommodation nearby and found a picturesque room through Airbnb.
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Where to begin? Logically, with the castle. All roads lead to it, and all roads lead from it, acting as the gravitational sun of the Windsor-ial solar system. One of the Royal Family’s official and the largest inhabited castle in the world, its origins date back to William the Conqueror in the 11th century.
The castle grounds are immaculate: lawns manicured to perfection, stonework so refined that it appears carved from butter, and fluttering flags dancing on steadfast turrets. The bastion’s silhouette is visible from miles around, resembling somewhere found in Far, Far Away.
Extending from the castle is the Long Walk: a 2.65-mile tree-lined avenue, that extends in almost a straight line. Serene, gorgeously envisioned, and again, clearly centuries old, it is a stunning place to run. I only scratched the surface of the 4,800-acre Great Park that extends past it, but nowhere else have I seen such old and glorious oaks.Hilary Mantel’s Bring Up the Bodies features Henry VIII riding to Windsor from London: such is the place’s timelessness, that one half expects him to appear at any moment.
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One Sunday morning, a fellow houseguest mentioned she was attending a service in the castle’s 14th-century St George’s Chapel. Though neither religious nor a churchgoer, only a fool would have denied the opportunity to join her.
Language alone, or at least my grasp of it, cannot capture the space. “Chapel” – suggesting modesty, intimacy, quaintness – is grossly misappropriates its grandeur. “St George’s (Micro) Cathedral” would be more apt. Extraordinarily ornate vaulted ceilings, ancestral crests and shields, representing great clans and families of an England long dead, and iconography worthy of Michelangelo.
This space is the final resting place of Queen Elizabeth II, Prince Philip, Henry VIII and Jane Seymour. It hosted Harry and Meghan’s wedding, and the blessing of King Charles and Camilla. Yet that Sunday, scarcely fifteen people inhabited that hallowed interior. An experience so uniquely Windsor.
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Adjacent to the town, only a short walk over a pedestrianised bridge, is Eton. Home to one of England’s most notorious and prestigious public schools, I ran through the town school on multiple occasions. The architecture was stunning, but more so was the clearly gargantuan quantities of wealth sunk over the preceding centuries.
Reports of The High Street’s Death are evidently yet to wash up on the Thames’ shoreline in Windsor. Every single restaurant and every shopping unit in the town centre was well occupied. Myriad middle-class chains thrive (see: Bills, Browns, The Ivy, Wagamama, Pizza Express, Zizzi’s, Gails), and many independent places seemingly do too. In Gails I spent a beatific afternoon, with my cousin’s week-old son nestled in the crook of my elbow.
I never went out drinking during my time in Windsor, but I have been well assured that it is home to many excellent breweries and pubs. I haven’t been to Legoland in many years but if my six-year-old self is deemed a respectable judge, it is a bloody good day out.
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My biggest qualm with Windsor, was mirrored, or perhaps illuminated, by my occupancy situation. With a normal spare room rental, you have a contractual agreement and operate as a tenant. There is a clear transactional understanding, and the terms are normatively and legally defined. Longer stays on Airbnb are different, however. A different dynamic is created, specifically, when you are renting in the live-in-owner’s house.
You are paying over the odds. But you are not a tenant. And you are not a guest either. It’s a purgatorial, limbo state, between rightful autonomy and gracious hospitality.
The room I stayed in was nice. As was the house in which the room was. As was the man who owned the house. But I couldn’t shake the feeling that I was staying in someone else’s house – never quite relaxed, never quite at home, never quite carefree.
This sensation parallels my broader impression of the town itself. A magnificent place, no doubt, but Windsor is not the home of its inhabitants: it is the home of the Castle, and those who reside in its walls.
They allow the commonfolk to make abodes in the city limits. They allow trade, and markets, and even the local peoples to come worship in their chapel. But do not get it twisted: Windsor will never be a place you can make yours, and it’s somewhere I could never call home.
Go visit for a weekend and enjoy its grand splendor. But if you want somewhere to call home, somewhere you can call yours, I’d maybe recommend you just ride on past.

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