Twinkling lights, decorated storefronts, snowy sidewalks, candlelit brownstones: There’s nowhere quite like Boston for the holidays.
In Cambridge, Harvard Square’s Charles Hotel (charleshotel.com) officially marks the season with their annual tree lighting, a rite of passage every Thanksgiving weekend. The neighborhood shines throughout the season with Sparklefest, a five-week-long lineup of holiday celebrations, ranging from indie markets spotlighting local vendors to menu tastings, musical merriment, caroling concerts from the Saint Paul’s Choir School, and lights displays, capping off on New Year’s Eve.
After strolling the Square, warm up with a taste of the South, from deviled eggs to gruyere mac-and-cheese at the new Margeaux, a supper parlor within the Porter Square Hotel (theportersquarehotel.com). Or duck into Bar Enza (bar-enza.com) at the Charles for potato gnocchi with braised rabbit. Care for a cocktail? The hotel’s Noir Bar (noir-bar.com) traditionally hosts the buzzy Maccabee Bar, pouring an array of Hanukkah-themed cocktails throughout the season. Don’t miss the signature latke “sour” with apple brandy, potato and lemon.
Across the river, The Boston Harbor Hotel (bostonharborhotel.com) hosts an elaborate annual Christmas brunch and lunch: overflowing raw bars, duck, prime rib, baked stuffed lobster, and more. Or simply slip in for a seasonal sip at the brand new Dark Bar, known for rare single-malt Scotches and cognacs. It was named one of Food & Wine’s best bars in 2024.
The hotel is also within easy strolling distance of the Boston Public Market
(bostonpublicmarket.org), with seasonal delights from local farmers and vendors; the Seaport’s Snowport, with illuminated menorahs and Christmas trees, winter games, and shopping (bostonseaport.xyz/holidaymarket); and the lights of Faneuil Hall Marketplace (faneuilhallmarketplace.com).
Celebrating with a crowd? Book the new Royal Suite at the Four Seasons Hotel Boston (fourseasons.com/boston), a 2,590-square-foot homage to a Boston brownstone, overlooking the Public Garden and the city skyline. Curl up by the marble fireplace; toast at the martini bar; and entertain up to a dozen friends or family members in the formal dining room—or sink into a velvet banquette and screen a holiday classic in the private cinema room.
Blocks away, shop Beacon Hill boutiques or settle in for a “Nutcracker” performance from the Boston Ballet at the Citizens Opera House (bostonballet.org). Sister hotel Four Seasons One Dalton (fourseasons.com/onedalton) is known for going all out during the holidays, with a pop-up lobby chocolate bar and a stylish high tea at their mod Trifecta lounge.
And, while spending too much time with family over the holidays might feel like punishment, The Liberty Hotel (libertyhotel.com) makes that sensation stylish: the former Boston jail is now an elegant hotel, known for dazzling, upside-down Christmas trees hanging from their 90-foot lobby rotunda. From there, it’s a short jaunt to Beacon Hill’s annual Holiday Stroll, held on the first Thursday of December: charming Charles Street buzzes with music, lights displays, and designer shopping—and, best of all, the street is closed to traffic.
Traveling with tots? Check into the Fairmont Copley Plaza (fairmont.com/copley-plaza-boston). Their Cori on the Shelf package comes with a stuffed animal, milk and cookies, and seasonal swag honoring the hotel’s black Lab canine ambassador, Cori Copley, often spotted holding court in the lobby. For a more sophisticated night, book their Cheers to the New Year package, with a complimentary bottle of Perrier-Jouët and one of six tables at their cozy house restaurant, OAK Long Bar + Kitchen (oaklongbarkitchen.com).
It’s the ideal way to fortify before venturing out to Boston’s First Night celebrations, from concerts to fireworks to parades, which run through midnight throughout the city. Too much revelry? Checkout isn’t until noon.
