I wanted to book a 4 star room in the Kaanapali - Lahaina area for October 10 through October 14 but the prices were very expensive on Hotwire ($231 a night) and Priceline Express Deal ($215 a night). So instead, I found that if I were to break my trip up into two pieces, the Priceline Express deal from 10/10 to 10/13 was $175 a night and the Priceline Express deal for 10/13 to 10/14 was $143 a night. So I decided to bid twice and I was able to come up with the following: From 10/10 to 10/13, I won a bid for 4* Maui (Kaanapali - Lahaina) The Westin Maui Resort and Spa at $165 a night From 10/13 to 10/14, I won a bid for 4* Maui (Kaanapali - Lahaina) Hyatt Regency Maui Resort & Spa at $130 a night While its not ideal to change hotels for one night, according to my wonky calculations, I will save approximately $190 by staying in two different hotels. Plus, we will get to check out another pool setup during our stay.