Basically, the best advice I can give is two-fold: be patient and follow your gut. And, of course, use the PRICELINE and HOTWIRE links on BetterBidding.com. I don't think there's a good time or a bad time. To me, it's a two-part system: how far out it is and my gut feeling when I'm attempting to book. For part one, take my story for example. We're going to Europe June 17-July 1 (Barcelona - Rome - Lucerne - Brussels - London - Shannon). Right now we're three months out for the trip. I started looking at HW/PL in December (about 6 months out). I didn't see anything I thought was a good deal, so I didn't book (which is part two). Of course, I used BetterBidding.com as a compass In January, things started looking better price-wise, but I still waited. Enter February, when I got a steal of a deal: $49 in London for June! (See my list of dates booked, method used, and prices below.) This weekend (March 6-7) I hit a roll with great prices, so I booked quite a few. I'm currently holding out for Rome and Dublin/Shannon because my gut tells me I can get a better price than what I've seen so far. FYI, booking.com's parent company is...wait for it...wait for it: Priceline. :) Hope this helps! :) AFG --- Wins So Far for Europe (June '09) Trip Method (Hotel / City / Reservation Date / Stars / Winning bid) Date booked Hotwire.com (Holiday Inn Camden Lock / London / June 28 / 4* / $49) 02.13.09 Marriott.com (Swindon / June 26 - free, used points) 03.07.09 Hotwire.com (Tryp Apolo / Barcelona / June 18-19 / 4* / $52) 03.06.09 Booking.com (Schloss Hotel Swiss Chalet / Lucerne / June 22-24 / 3.5* / $84) 03.07.09 Priceline.com (NH Kensington / London / June 29 / 4* / $57) 03.07.09