Montauk, New York
Most of the town’s seventies-era motels shutter after Labor Day, but the recently renovated Solé East (from $140; soleeast.com) will stay open through the end of November. The white-on-white rooms look straight out of the Bahamas, while the Backyard restaurant has fireside tables that’ll have you thinking Catskills. After November, opt for East End mainstay Gurney’s Inn Resort & Spa (gurneysinn.com), which has a winter-getaway package for two through December 18. An ocean-view room with breakfast, dinner, and spa treatments is $566 per person for a two-night stay.
Southold, New York
On the other side of the Sound, North Fork Table & Inn (from $275; northforktableandinn.com; closed during January) keeps its rates the same year-round, but the B&B gives guests a $100 credit toward lunch or dinner in the off-season (available December 1–April 1). Given the owner’s résumés—Claudia Fleming is a former pastry chef at Gramercy Tavern, and husband-chef Gerry Hayden ran the kitchen at Aureole—it’s a great deal. The pair incorporate Long Island wines, locally grown produce, and seafood from Peconic Bay onto daily menus.
Atlantic City, New Jersey
Despite the neon “Cash for Gold” signs across the street, the Chelsea (thechelsea-ac.com) offers a more sophisticated version of life in A.C. The rooms are pretty enough, with white fluffy linens and backlit mirrors, but it’s the communal fifth floor—with its velvety game room, Stephen Starr steakhouse, and couch-strewn “living room”—where everything happens. Ask for the Rescue Package (from $199 through March). You get an overnight stay, a breakfast for two at the reborn Teplitzky’s diner, a $50 gas credit, and two rolls of quarters for the Tropicana slots next door.
Cape May, New Jersey
During the winter, the southern-Jersey resort feels like the romantic island getaway it actually is, buffeted by stormy gray seas and wind-blasted beach dunes. Check into the 24-room Virginia Hotel (from $99, down from $290 in August; virginiahotel.com) and devour plates of fresh calamari ($10) in the Ebbitt Room. Go wine tasting at Cape May Winery, open year-round (capemaywinery.com). Or hit the marble-and-ebony Brown Room at Congress Hall (from $99, down from $349; congresshall.com), where you can nurse a Blue Pig Apple Knocker (mulled cider with splashes of rum and brandy) beside the bar’s blazing fire.
Block Island, Rhode Island
Snag one of summer’s most sought-after rooms at the popular 1661 Inn (blockislandresorts.com). For $120 (a third of peak-season prices), you’ll get a gas fireplace, unobstructed ocean views, and a giant breakfast of Belgian waffles and bacon. Walk off the smorgasbord by hiking the dramatically steep Mohegan Bluffs, then defrost over cups of New England clam chowder at the locals-only Bethany’s Airport Diner (401-466-3100), one of the few dining options still open from October to March.
Kennebunkport, Maine
Yes, Maine is really cold. But it’s also beautiful, with a craggy coastline, snow-topped lighthouses, and acres of deserted winter woods inland. Stay at the Beach House Inn (from $169; beachhseinn.com) or upgrade to a newly renovated room at the White Barn Inn (from $295, down from $420 in summer; whitebarninn.com). The inn’s restaurant, housed in side-by-side barns (closed January 5 through 22) is manned by chef Jonathan Cartwright, who gives private cooking classes focused on warm winter fare (from $300, including a four-course dinner).