I'm looking for a place to stay in the south of town.
There are 3 guesthouses and 1 hotel in the south of town. Is there a particular price range you're looking for?
I definitely want to stay in a hotel, not a guesthouse. Is the hotel moderately priced, and does it have free parking?
There are no moderately priced hotels in that side of town. Would you like to try a different side of town?
I see, well how about a guesthouse in that area with free parking?
Yes I have two guesthouses in that area. Would you be interested in either of them?
Yes, which one has room for six guests?
For what day would you like me to try booking for? 
I need it on Sunday, for 3 nights.
Unfortunately, neither of those guesthouses can take in 6 guests for three nights on Sunday. Might I suggest another day or a shorter stay?
OK, can you accommodate 2 nights then?
Unfortunately, neither guesthouse can accommodate 2 nights. Is there another date you'd like to try for, or would you like to try for 1 night rather than 2? 
Is there any other options that we can look into?
Unfortunately those are the only options within that price range. Would you like me to look for a more affordable option?
Just please book for that room for 2 nights.
I'm sorry, as I previously mentioned neither guesthouse can accommodate that request. How about another area of town?
Are you certain there is not either a guesthouse or hotel in the south with free parking for 2 or 3 nights Sunday for 6 people?
Not  based on Sunday arrival - would you like to try another day or shorter stay?
Let's try again. A moderately priced guesthouse in the south with free parking. Sunday, 2 nights, 6 people. 
I apologize. There is no hotel or guesthouse in the south with free parking that can accomodate you with those details. A different day or a shorter stay may work. 
Could you check another area of town perhaps that can accommodate 6 guests for 3 nights starting Sunday with a moderate price and free parking?
I'm sorry to tell you that there is no hotel in any area of town that meets those requirements and can accomodate 6 for 3 days from Sunday. 
Shoot.  Well, okay, how about two nights?
I have booked 6 into Acorn Guest House for 2 days starting Sunday. It is moderately priced, in the north, with parking. Reference number 0GNWIGNC. Is there anything else?  
I need a train from cambridge to broxbourne that leaves after 8:15 on tuesday.
Train TR7656 departs Cambridge on Tuesday at 09:01.  If this works for you how many tickets do you need booked?
I need 6 tickets please.
I have booked 6 tickets for train TR7656 leaving at 9:01 Tuesday. The total fee is 107.4 GBP payable at the station and the reference number is SGNRTY27. Is there anything else I can help you with?
That is all, thank you.
Awesome. Take care!