Windsor

The castle, the Long Walk, and the shortest Thames crossing to Eton — 30 minutes east of Reading and always busy.

Windsor is 30 minutes east of Reading and does not need much introduction — the castle is the oldest continuously occupied royal residence in Europe, and its silhouette over the Thames dominates everything. The town below is a mix of tourist honeypot (Peascod Street, the Royal Shopping Arcade) and genuine market town (Windsor & Eton Central Station, the Two Brewers pub on Park Street). Eton College sits across the Thames via the pedestrian bridge. At 9pm the castle sits floodlit above and the tourists have mostly gone; the pubs on Church Street and Park Street are where the actual town drinks.

Stay in Windsor for the royal-town experience with the castle on your doorstep and easy London trains. It's expensive, and the volume of visitors in high season is genuinely tiring — the castle car park queues start at 9am on summer Saturdays. Don't stay here on a budget or if crowds bother you. What's overrated: the tourist trap restaurants on Peascod Street — chain quality at 30% premium. What's underrated: the Long Walk, 4 km of straight avenue south of the castle through Windsor Great Park to the Copper Horse statue — free, uncrowded once you're 500m in, and stunning at sunset.

Day-trippers arrive mostly for the Changing of the Guard outside the castle gates — usually mid-morning on alternate days, free to watch from the pavement on Castle Hill, and worth timing your visit around rather than fighting the crowd blind. Families tend to split the day between the castle and Legoland, with the Thames towpath and Alexandra Gardens as the quiet middle ground — a flat riverside green good for a sandwich away from the queues. French Brothers river cruises leave from Barry Avenue, a short walk from the castle, and are the easiest way to see the castle from the water without booking anything in advance.

Windsor in November and January is a different town — half the coach parties gone, the castle interior still open, and the Long Walk empty enough to have to yourself on a weekday morning. The Christmas market on Castle Hill runs through December and is worth the extra crowd if you are visiting anyway. Stay here if you want the castle walkable from your room and don't mind paying London-adjacent prices for it; if you are on a tight budget or travelling with a car and don't need to walk to the castle gate, Maidenhead or Bracknell are 15-20 minutes away and considerably cheaper.

Where to stay in Windsor

The Windsor Trooper on Thames Street, close to Windsor & Eton Riverside station, is the best base for castle-facing rooms and an easy walk back from the Church Street pubs — expect £140-£220 in summer, £100-£160 in January and February. The Oakley Court, a Gothic riverside mansion at Water Oakley on the road to Maidenhead, suits a quieter country-house stay with the castle a ten-minute drive away, from around £180. Holiday Inn Express Windsor by IHG, near the Legoland approach road, is the reliable budget option at £95-£135 and books out fastest for peak Legoland weekends. Windsorian Experience suits longer stays or a family group. Under £90 a night is essentially unavailable in Windsor itself in high season — for cheaper beds, base yourself in Slough or Bracknell. Book the Windsor Trooper if the castle view matters more than the price.