For business - The Diana Majestic in Milan, where I've been a regular for at least 10 years. It's smart but friendly, comfortable and unpretentious - the lobby isn't intimidating and you don't feel that you have to dress up just to drink in the bar. With 150 rooms, it's quite big so there are usually rooms available and you don't have to book months in advance, but it still feels homely and unpolished, which I love. It has a garden at the back (unheard of in Milan), which is good for impromptu meetings, and the whole place manages to seem off the beaten track even though it is within walking distance of the town centre. Most important of all, it does a great breakfast.
For pleasure - The Grand Hotel d'Angkor in Cambodia is a jewel that can easily stand up to the best hotels in the world - it is somewhere I would recommend to anyone. An old colonial-style hotel (pictured), it was abandoned for many years but restored and reopened by the Raffles Group in 1997. It has an absolutely paradisaical setting right on the doorstep of the breathtaking temples of Angkor Wat. You go sightseeing in the morning, return to the hotel for a splendid meal and then go out again after four when it is cooler. It has a truly faraway feel, the service is fantastic and the Cambodians themselves are amazingly friendly. It is almost unheard of for me to holiday in the same place twice, but I enjoyed my first visit so much that I went back again last year with my family.