Boston Holiday Travel Deals

While New England hasn’t always been known as the friendliest part of the country (sometimes it’s just too cold to stop and talk to your neighbor), the holiday season puts even the most rough and tough New Englanders in merry spirits. Boston combines quaint New England charm with world-class Boston attractions for a good time that you just can’t get anywhere else. And if you’re looking for a mellower vacation, don’t forget about New England’s beautiful vacation destinations, like Cape Cod and Martha’s Vineyard.

Of course, we wouldn’t recommend New England if we didn’t know Boston holiday travel deals were some of the best around. Whether it’s outdoor recreation you’re looking for or some good old fashioned holiday light sightseeing, Boston’s got it all.

Boston Hop On/Hop Off Trolley

For the best views of Boston’s myriad of holiday displays and decked out Christmas trees among the landmarks and historic Boston attractions for which the city is famous, hop on board a Boston Trolley Tour. You’ll see all of Boston’s many distinct neighborhoods, from Beacon Hill to Fenway, as well as monuments like the Old State House and Bunker Hill. Best of all, you can hop on and off as you please, stopping at the attractions that interest you most.

Skywalk Observatory & the “Pru”

Boston’s Prudential Center is a well-known architectural landmark in Boston, as well as a classy place to shop and dine. In fact, it’s the ideal place to do any Christmas shopping left on your list. The Prudential Tower is also home to the highest observation deck in New England, the Skywalk Observatory. This 50th-floor observation deck offers views of the city that are stunning all year around, but especially during the holiday season. If you can catch Boston from above with snow on the ground, you’re in for a majestic experience.

Faneuil Hall & Quincy Market

The country’s oldest marketplace is where you’ll still find all the hustle and bustle happening around the holiday season. The Faneuil Hall Christmas Tree, which is currently the tallest tree in the Northeast, stands proudly with its 300,000 lights and strobes. The Faneuil Hall Marketplace is also a great place to take a stroll—the cobblestone streets only add to the holiday charm—and an even better place to find some unique holiday gifts.

Boston Common & The Public Gardens

"The ducklings kept right on quack-quack-quacking."

“The ducklings kept right on quack-quack-quacking.”

The Boston Common is the anchor of Boston’s downtown, and as the first urban park in the United States, it offers a whole lot of history. During the holidays, the park’s tree-lined pathways are gleam with festive lights, and bundled up couples and families head to the Frog Pond, which is transformed into an ice skating rink during the winter months. If you can brave the cold for long enough, the Boston Common is also the start of the Freedom Trail Walking Tour, one of the most recognized Boston attractions. You’ll also want to take a trip over to the Public Gardens, the smaller, more manicured park next door to the Common, and see what holiday outfits the beloved Make Way For Ducklings statues are wearing!


For the best savings on holiday attractions in Boston, check out our Boston Holiday Attractions Package, guaranteed to save you money on three top attractions: The Boston Hop On/Hop Off Trolley Tour, the Skywalk Observatory, and the Isabella Stewart Gardner Museum.

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