With all of the traveling we have done, I have only used Priceline once and that was for a one day rental from Ft. Myers airport to the Ft. Lauderdale airport.
My daughter and I just returned from a long weekend in Boston. With hotels in downtown Boston averaging over $200 per night (plus 14% tax) I decided to give Priceline a try. I started bidding about two weeks out, looking for a 4 or 3 1/2 star hotel in either the Quincy Market area or just west of downtown in the Back Bay/theater district. My starting bid was $100.
I proceeded at follows:
I selected the Quincy Market area and a 4 star hotel.
When my bid wasn't accepted I added the Theater District
When my bid still wasn't accepted I eliminated the theater district selection and went to a 3 1/2 star hotel.
My bid still didn't get accepted so I added back in the theater district for a 3 1/2 star hotel.
During the entire time, from 8 to 14 days out, I had no luck. Then, literally one week out, I got a 3 1/2 star hotel in the theater district for my $100 bid ... Hilton Back Bay (which I'll review later). For curiosity's sake I went to the Hilton website and if I had booked online, the same hotel would have cost about $190 per night with an AAA discount. So I did good.
But then I got to thinking. In retrospect what I should have done was continue to look for a 4 star in the Quincy Market area, at $100, until about 3 days out. I might have gotten lucky. If I didn't get lucky, I could have always added in the theater district and/or gone to 3 1/2 star at that point.
I am not a patient person and I have to admit waiting like this to book a hotel was difficult. I'm wondering if I should have been a bit more patient and given my first choice (Quincy Market/4 star) another day or two to come through. Either way, it was great having saved over $400 for our Boston stay, money that more than paid for the extras ... food, sightseeing, theater, etc.