How to Priceline Like a Pro

Not only do I love to travel – I love planning travel. It’s a huge puzzle and I enjoy fitting all the pieces together to create the perfect adventure. How will we get from point A to point B? What will the currency be at point B? Is it within walking distance of point C? And is there a restaurant at point C with rave reviews?  (I already know I’m weird so you don’t have to tell me.) When I traveled to Europe for three weeks last summer, my travel companions teased me about the 3-ring binder I brought along but I think they were secretly grateful. If it involves research, making a reservation, or packing a suitcase, I’m so on it. I have an inner circle of websites that I’ve come to depend on. I can work Trip Advisor, Hotwire, Priceline, VRBO, Seat Guru, Luxury Link, and Better Bidding like a boss. I own those sites like Ke$ha owns glitter.  If you’ve been intimated to try Priceline’s “Name Your Own Price” feature, have no fear – the expert is here!

Hotels want to fill their rooms to make money. If they have a significant amount of rooms available during your travel dates, they’d rather you pay half the price than to not make any money at all. They don’t want you to know they are willing to accept half the price so the hotel name is kept a secret until you’ve paid. It’s intimidating for first timers but once you know how to make this site work for you, you’ll LOVE it. Priceline has become like a verb for me, similar to Google or Chi. I’ve “Pricelined” hotels everywhere from Sedona to Spain and haven’t had a bad experience yet. 

To place a bid for the “Name Your Own Price” feature, you’ll need to make the following decisions: destination, travel dates, neighborhood, star rating, and your bid per night. Follow these Priceline tips to ensure you are not only getting a good deal but placing an educated and informed bid.

Where will you be going? (First things first.)

Research the area! Is there a central location where you really want to stay? Do you want to be on the beach? Or downtown? Is there a shady area you want to avoid? Decide a couple of neighborhoods you’d be happy to stay in. I usually do significant research, then put all my eggs in one basket and fight to the death to get it. (If you’re not as type-A as me and can be flexible, then Priceline is your new best friend.)

Do some undercover work. This is where Better Bidding comes into play. This website is basically a massive forum where people are not only posting which hotel they won through Priceline or Hotwire but also how much they paid.

1. From the Better Bidding homepage, scroll down until you find the state you are traveling to. There is an international section at the bottom if you are traveling abroad. Let’s say I’m traveling to New York.

2. The next page allows you to choose between Priceline forums and Hotwire forums for New York. I usually book through Priceline so I’m going to click on the Priceline forum.Here you can see travelers posting the neighborhood they booked in, the star level, and how much they paid.

3. At the very top of this message board, click on “Priceline Hotel List – New York”

4. Click on the city you are traveling to.This will bring up a list of neighborhoods in that city that are available through Priceline.

5. Click on the neighborhoods you are interested in. Let’s be bold and say I want to stay in Times Square.

6. Now you can see every hotel available through Priceline depending on the star level. If I bid on a 4.5 star hotel in Times Square, I know I’ll get The Intercontinental because it’s the only 4.5 star in that neighborhood available through Priceline. Let’s say I’m happy with staying in a 4 star hotel – then we’ve got 9 options! At this point, I usually pull up every single option on Trip Advisor and check out their rating and read reviews. If I’d be satisfied with any of them, then it’s time to move on to the next step. If there are a couple I really don’t want to stay at then I might go up or down a star level to guarantee I’m staying at a hotel I want. The 4.5 star and 5 star in the Theater District both have great ratings on Trip Advisor so I’ve narrowed it down to 2 hotels I’d be thrilled to win.

Decide the maximum amount you are willing to spend per night and stick to it! This can sometimes be like a Wheel of Fortune slot machine for me. It’s bad. To help you have a better understanding of what you’ll pay, check travel websites that will reveal the name of the hotel like or Priceline’s regular booking system. I can usually count on paying at least 30% cheaper than what it’s currently priced at. I can see that for my travel dates The Intercontinental is priced at $354/night. This will make my starting bid around $175. I usually start around 40-50% off the standard rate just in case. I’ve snagged some great hotels by lowballing it!

Place your bid! If you don’t win your bid – this is just the beginning! I almost ALWAYS lose my first bid due to extreme lowballing. One of the downsides to Priceline is you can only place a bid once every 24 hours. In typical Cason fashion, I’ve found a loophole. Priceline will let you immediately place another bid if you are willing to add additional neighborhoods and/or change the star level you are willing to stay at. Because I definitely want to stay in a 4.5 or 5 star hotel in Times Square, all I need to do is find a neighborhood that doesn’t have a 4.5 or 5 star hotel available. If I’m not changing my star rating, and there isn’t a 4.5 or 5 star hotel in the neighborhood I’m adding, there is absolutely no way I won’t get a hotel in my original location. You following me? Totally okay to read it again slowly if you need to! Let me show you an example.

Open up a new tab and go to Priceline. Go through the same exact steps you did before (enter the city, travel dates, # of rooms, etc.) When I have Times Square checked, it shows 4.5 and 5 star hotels available. When I only have Brooklyn checked, there are no 4.5 or 5 stars available. So if I check that I’m willing to stay in Brooklyn or Times Square in a 4.5 or 5 star hotel, it’s not possible to get anything in Brooklyn. Every neighborhood you find that DOESN’T have a 4.5 or 5 star hotel available = another bid!

There are no 4.5 or 5 stars available in Brooklyn, Hell’s Kitchen, Long Island City, Lower East Side, Madison Square Garden, Morningside Heights, or Upper West Side so that means I have 7 additional chances to win a bid. Increase each bid by small amounts ($5 – $10 max) and as long as you started your original bid around 40% off the regular rate, you’ll most likely win!

Viola! Have any questions? Email me at and I’ll be happy to answer any travel questions you have! Do you know any insider travel secrets or websites? Leave a comment below so that all YCSWU readers can take advantage of your knowledge. Happy traveling!