6 Unexpected Winter Escape Ideas

It’s not too late for family travelers to book the ultimate winter escape. From a Christmas town in Maine straight out of a Hallmark movie to a tropical getaway in the Florida Keys, these destinations blend local traditions and festive flair.

Kennebunkport, Maine

Kennebunkport, Maine, was named America’s No. 2 Christmas Town by HGTV thanks to its seasonal transformation into a winter wonderland. The 44th Annual Christmas Prelude runs Dec. 4–14 and features lobster trap tree lightings, fireworks, caroling, Santa Claus arriving by a lobster boat and The Tinsel bar with festive cocktails. While there, stay at Cape Arundel Inn, an oceanfront property with holiday charm, dining options, stunning views, and a new pantry option celebrating local Maine products and the spirit of a New England holiday.

Cape Cod, Massachusetts

Enjoy seaside holiday traditions such as seafaring Santa arrivals, quaint holiday ships, Cape Cod Central Railroad’s Polar Express train rides and festive parades. The Wequassett Resort offers the ideal stay with its Enchanted Winter experience, featuring a tree-lighting ceremony, fireworks, a Merry Market, workshops in Mrs. Claus’s Cottage and more.

Rockaway Beach, Queens, New York

Located an hour away from Manhattan, Rockaway is New York’s most unexpected winter destination. The winter surf town features local holiday markets, winter villages and Parade on Rockaway. Guests staying at The Rockaway Hotel + Spa, a community-driven beachside retreat, can have brunch with Santa.

Catskills, New York

Escape to snow-covered peaks and small mountain towns in the Catskills. Enjoy the great outdoors with skiing and snowshoeing at Hunter and Windham mountains, Christmas markets, and festive parades. Stay at The Henson for holiday décor, mountain views and delicious meals at Restaurant Matilda.

Florida Keys, Florida

Escape the cold and enjoy Florida Keys celebrations, such as lighted boat parades, Harbor Walk of Lights and a 7-mile SantaCon. Book a stay at The Perry Hotel & Marina in Key West for local artist showcases, festive waterfront dining and more. At Isla Bella Beach Resort in Marathon, enjoy its Festive 10 Days of Holiday Programming, including an outdoor oceanfront ice-skating rink, Santa visits and family-style meals.

Donnelly, Idaho

While Idaho might not be your first idea of a winter getaway, Tamarack Resort, a mountain retreat between Lake Cascade and West Mountain, offers a festive alpine village with new winter and ski season upgrades. Enjoy Christmas tree lighting events, themed workshops, “Santa Skis for Free,” full moon snowshoeing and much more.