Checkendon is a pleasant rambling Chilterns village between Woodcote and Stoke Row, north of the A4074 between Wallingford and Reading. It is surrounded by beech woods, with bluebells in the spring, and the rich colour of the autumn leaves. The older part of the village is at one end and is centred around the Church of St. Peter and St. Paul. The area around Checkendon Court and St. Peter's and St. Paul's Church is a conservation area.

The area has a long history of settlement and the parish itself has a record of continuous settlement since the C7 AD. It is listed in the Domesday Book under the name Cecadene, which is Old English for Ceaca's hill or hill-pasture. The Church of St. Peter and St. Paul was built in the C12 by friars from the monastery of Bec in Normandy and probably replaced an earlier timber building which in turn replaced an earlier pagan structure. The lych-gate commemorates the men who fell in the two World Wars.

Next to the church is a fine Tudor mansion known as Checkendon Court with its long drive flanked by clipped yew trees and a pair of imposing cast iron gates. The drive to Checkendon Court runs by the church and part of its length is a public footpath. This estate dates from 1030. Across the road from the church are several timber framed buildings, among them one that used to be the old smithy, also the former post office and the village pub. Next to the church is the primary school, village hall and new rectory.

Newer development is at the other end of the village and here, in a C20 bungalow, is the post office and stores. Between the newer part of the village and the conservation area is a large village green. Around and about the village are dotted a number of country houses.