Cheltenham

Cheltenham sits right on the western edge of the Cotswolds, and it makes a brilliant base if you want countryside by day without giving up good restaurants, bars, shops and proper evening options. The town is best known for its Regency architecture and festival calendar, but its appeal is really the mix: elegant streets around Montpellier and the Promenade, green spaces such as Pittville Park, independent food and drink, and easy access out towards the hills and villages.

What Cheltenham does best

Start in Montpellier and the Suffolks, where the town feels at its most distinctive. You will find handsome terraces, independent shops, cafés and plenty of places to stop for a drink. From there it is an easy wander towards the Promenade and town centre, or north towards Pittville and the Pump Room for a quieter, greener side of Cheltenham.

Cheltenham is compact enough that a weekend does not need to feel rushed. You can spend a morning walking the town, take a long lunch, then head out towards Leckhampton Hill or the wider Cotswold countryside before coming back for dinner.

Food, pubs and evenings

This is one of the reasons we think Cheltenham works so well as a Cotswold base. There is far more choice after dark than you will find in most villages, from relaxed pubs and taprooms to cocktail bars, independent restaurants and special-occasion dining. No.131 is one of the town's best-known addresses for drinks, dining and a stylish stay, while Dunkertons at Dowdeswell is an easy stop for cider and a more laid-back afternoon just outside the centre.

The Brewery Quarter is useful when you want everything in one place, particularly with children, on a rainy day or when a group cannot agree on what to do next.

Festivals and racing

Cheltenham calls itself The Festival Town for good reason. Its annual calendar includes major literature, science, jazz and music festivals, alongside a long list of smaller cultural events. The racecourse brings a completely different atmosphere, especially around the Cheltenham Festival and Gold Cup in March, when the whole town becomes noticeably busier.

If you are visiting for one of the headline events, book accommodation and restaurants earlier than you normally would. Outside those peak dates, Cheltenham can feel surprisingly relaxed.

Good for families and dogs

Parks, nearby hills and the number of casual places to eat make Cheltenham easy with children. Pittville Park is a useful option when you need space to run around, while the town also gives you indoor fallbacks when the weather turns. Dog owners have plenty of pub and walking options too, with countryside quickly accessible from the edge of town.

Why stay here rather than in a village?

Choose Cheltenham if you like the idea of exploring the Cotswolds during the day but want more choice in the evening. You can still village-hop, walk and drive through the countryside, then come back to somewhere with taxis, shops, restaurants and bars. For a first Cotswold weekend it is an especially easy base, and it works well for couples, families and groups who want a little more going on around them.