Any recent experience with overlapping stays? I have had reservations for overlapping dates numerous times before, but always cancelled the other reservation in plenty of time. I have a situation I am trying to figure out. I currently have a 4 night stay booked at Hotel A for a very good rate. Plans have changed slightly and I now would like to do 3 nights at Hotel A and 1 night at Hotel B (the 4th night) in another town nearby. When I went to book Hotel A for 3 nights, it shows as sold out but I can book with the Diamond Guarantee for double my current nightly rate... so 3 nights would be about $400 total more than my current reservation for 4 nights.

If I edit my current 4 night reservation to go down to 3 nights, I would essentially have to rebook at the new rate, correct? One option is keep my 4 night stay but leave on day 3. I could easily book a Marriott or non-Hilton for the "Hotel B" single night stay and Hilton would be none the wiser I suppose. But I actually would prefer a Hilton property for my single night stay. So I would be checked in to two Hilton properties at the same time in that situation. I don't want Hilton to cancel my second stay and I would like to earn points for it if I'm paying for it. Anybody had a similar situation recently?