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The parish is situated in a part of Sussex where the Low Weald becomes the High Weald with the northern part significantly higher than the southern. Historically it is one of the largest parishes in the county and reputed to be in the exact centre of Sussex. It was also for many centuries one of the poorest and unsurprisingly was the site for the district workhouse during the 19th century. This poverty also ensured that a large number of the commons within the parish survived periods of enclosure particularly the 17th century when virtually all of the commons of the neighbouring parishes to the west disappeared. More information can be found on the Chailey Common description.

The original settlement of Chailey lies in the centre of the parish but the bulk of the population lives in either South Chailey or North Chailey both those communities having grown up from the 19th centuries around the South and North Common respectively. There are two major roads through the parish, the A275 runs north-south and is the Lewes to East Grinstead road which follows the line of the old medieval Lewes to London route. The A272 runs east-west and is a newer turnpike constructed in the late 18th century. Both cross each other at North Chailey. A station existed which was shared with Newick as it lay midway between the two from 1882 to 1958 when the line was shut. Newick & Chailey station was the next station south of Sheffield Park the current terminus of the Bluebell Railway.