The Winston Guesthouse is conveniently situated close to the popular Bicester Village designer shopping outlet, the town centre and other local shops, with just a 20 minute walk to the outlet and a 15 minute walk to the town centre. There is a regular bus service from right outside the guesthouse to the historic Oxford city centre, and there are also public transport connections to Woodstock and neighbouring towns.

The guesthouse also has very close business connections to neighbouring towns such as Oxford, Milton Keynes, Stratford-upon-avon, Buckingham, Swindon, Northampton, the M4, M40 and the Bicester train station.