This may seem like an odd post coming from a travel agent, but my financial background runs long and deep. Traveling (and traveling nicely) does not have to be as expensive as one may think.
Using Hotwire, Priceline, or Last Minute Travel can really pay off once one can "figure out" how it all works. I have been known to cross reference other websites such as Trip Advisor or Better Bidding. I would say that I find Trip Advisor works best for Hotwire and that Better Bidding works best for Priceline. Last Minute Travel can sometimes be extremely easy as they sometimes post photos of the interior of the hotels. It is easy to cross reference between any of the other travel websites as they usually post the same stock photos. The majority of the time when booking on any of the three websites I am 99% sure what hotel will be revealed.
The first time that I recall making a purchase when I was 99% certain of where I would be staying was in July 2005. We were heading to Fort Lauderdale for a week. I really wish I remembered what we paid (as nothing shows up in the history on the LMT website). The hotel was the Sheraton Yankee Trader. The hotel was beachfront, we could even see the ocean from our room!
Now on to more specific examples from Hotwire (Thank you, Hotwire, for having the winning history!)...
July 2004 - Miami Beach, FL
Sixty Sixty Resort and Hotel (at the time was a Holiday Inn), 3 Stars, $50 per night.
According to TA - Awful reviews, would not recommend!! In 2004, it was nice.
May 2005 - Salt Lake City, UT
I loved it there! Actually wanted to stay there the last time I was in town. Priceline did not agree.
June 2008 - Myrtle Beach, SC
Sheraton Convention Center, 4 Stars, $89 per night. Retail is over $200 per night.
$89 is not a bad deal for booking a same day, Friday night, summer time stay in Myrtle Beach.
May 2009 - Honolulu, Hawai'i
Hilton Hawaiian Village, 4 Stars, $102 per night. Retail starts around $200 per night.
Again, another favorite!! Great location, we could walk pretty much anywhere. Plus, there was a bus stop right out front.
Holiday Inn Sunspree Resort, 3 Stars, $89 per night. Retail is over $200 per night.
The hotel was ok. No real complaints, my guess is that the high retail is due to the proximity of the hotel to the west entrance to Yellowstone National Park. I would be willing to stay there again.
May 2010 - Teton Village, WY
Snake River Lodge and Spa, 4 Stars, $49 per night. Retail is around $300 per night.
Probably my absolute favorite! I already want to visit again, but prefer the $49 price tag.
May 2011 - Myrtle Beach, SC
Embassy Suites, 3.5 Star, $111. Retail is over $200 per night.
Not bad for a holiday weekend. I would definitely stay there again.
May 2010 - Salt Lake City, UT
Honestly, the hotel was older but extremely clean. I would stay there again. Our room was huge, and well, really pink! Very easy walk to Temple Square.
March 2011 - San Juan, Puerto Rico
Intercontinental San Juan Resort and Casino, 4 Star, $115 per night. Retail starts at just over $200 per night.
We were upgraded to the club level which required a key card in order to even enter the wing. The room was nice. The pool and beach were great! I would not ever pay retail to stay here, but we would definitely be willing to stay here again. Our sitting area overlooked the pool.
March 2011 - San Juan, Puerto Rico
Sheraton Old San Juan Hotel, 3.5 Stars, $83 per night. Retail is around $150, but much higher the night before cruise ship turn around.
Convenient!!! We had terrible neighbors (LOUD!). The hotel was clean, the walls were paper thin. Location, location, location would bring us back. Our room overlooked the cruise ship docks.
Savings with Priceline and Hotwire can be paired with getting paid to shop online from Ebates. Cash back for Priceline ranges from 1% to 4.5% depending on what services are purchased. Hotwire's cash back rate is 2%. I am not a huge online shopper, but I have earned $51 since I joined in August 2010.