I need a place to stay, preferably a guesthouse with free wifi 
Sure, is there a particular part of town you prefer?
Still deciding that part but would definitely need the expensive price range.
It looks like there are no expensive guesthouses with free wi-fi. Are there any other place you would be interested in?
Can you find any expensive hotels then?
There are 5 hotels that match your request. To help you further I will need to know what part of town you want to be in.
The part of town does not really matter to me. Can you recommend something please and let me know whether or not they have free parking?
huntingdon marriott hotel is a 4 star hotel that would fit all your needs. It does have free parking. It is located in the west. Would you like me to book you a room?
Not at the moment. I need info on a place to dine, in the centre area that serves Italian food.
Okay.  Well, Italian restaurants are pretty popular in that area as there are many to choose from.  Do you care about the price range?
no. recommend and give me the price range, postcode and phone number
Okay, sure.  There's a great restaurant called Pizza Express located at Regent Street City Centre.  They are moderately priced and their phone number is 01223324033.
Thank you goodbye
enjoy your stay in cambridge