San Francisco, From $108 a Night
This festive hotel package is valid over the holidays and includes ice-skating at Union Square.
Free spirits tend to find common ground at Casa Zen.
This hotel is just off one of the best breaks on the Nicoya Peninsula.
An Adirondack-style lodge houses Amor de Mar's 11 rooms, paneled in dark wood and decorated sparely, so as not to distract from the views (best from the second-floor porch).
Billing itself as a surfer hangout, this hotel also offers lessons.