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Step 1: Find a hotel or bed and breakfast with a horrible website.

Step 2: Offer SEO work, fixing typos, implement webervations or custom online reservation tool, general clean up in exchange for free nights.

I've found most proprietors of mom n pop hotels/bed breakfasts have no clue how to find a good designer/developer to help them with their site.

http://airbnb.com ?

priceline.com?

I got $120/night hotels for $40/night.

Yeah, priceline is high risk/reward. Sometimes you get an amazing deal, sometimes you get stuck in a place with bedbugs (I've been there). Although you can probably largely protect against this by only specifying hotels with 3+ stars.

Ask HN: Hotel Booking Hacks?