We're a big fan of Montauk in any season, but the tip of Long Island can be a particularly relaxing, sedate getaway in the dead of winter. (It's cheaper to stay out there too.) And did you know there's ice-skating at the lighthouse?
We did a bit of research into Montauk in the cold months and found some helpful sites for you.
General Background:
Trip Advisor Forum: Montauk in Fall & Winter
Montauk Online Guide
Lodging:
On Montauk -- search available properties.
Montauk Manor -- Tudor-style resort with lots of character
Long Island Host Directory -- Nice list of Montauk hotel options
Excursions:
Article on winter cod fishing excursions from Montauk
Must Visit:
The Montauket Restaurant and Bar We flag this as a must visit for the great coast and sunset views and highly recommend visiting for at least a drink, if not dinner one night. The decor is a bit divey, but the character and the views more than make up for this.
Video:
Here's a some footage detailing one local's love affair with Montauk in winter. [UPDATE: This video is no longer available.]
Need more suggestions? We have a few: