This beautiful city is quite affordable in the winter. Located right next to the border with Mexico, San Diego will brighten your mood with its warm weather and overabundance of fun activities from beach-front ice skating rinks, concerts, and holiday shopping. If you want to experience world-class surfing without having to break the bank, San Diego is your destination. Surfing there is on the great American bucket list. It has awesome wave pools in addition to a plethora of good surf spots. You can find hotels for under $100 per night (usually at their lowest this time of year).