Winter Getaways
Winter getaway in Massachusetts: dinner in front of a fire; snow-dusted explorations
Winter settles on New England in a mist of snow-dusted streets and meadows, holiday lights, and hearty food in front of a crackling fire. Plan a winter getaway to a classic Massachusetts lodging that suits your tastes: from a bed-and-breakfast inn racing the town green in a Berkshire mountain village to a boutique hotel tucked among the crooked old street of Boston or Cambridge to a windswept waterfront inn along the shore. Plenty of amenities – fireplaces, hot tubs, traditional winter foods – await you, prepared and served with comfort, cleanliness, and your health in mind.
8 listings
Deerfield, MA
Deerfield Inn
81 Old Main Street 413-774-5587Historic Deerfield, and its famous inn, both have a special sparkle in the winter
What a lovely town Deerfield is in the winter, the snow sparkling on the roofs of its 18th- and 19th-century homes. And right in the middle of Main Street is the cozy Deerfield Inn, where winter travelers have found crackling fireplaces and warm hospitality since 1884. The 24 rooms in the main inn and carriage house feature period reproduction furniture, antiques and comfy reading chairs. Spend your days hiking up Mount Sugarloaf or skiing, snowboarding and snow tubing at Berkshire East, visiting the area’s many art and history museums, breweries or the Yankee Candle Village store. Come back to relax by the fire in the inn’s Beehive Parlor or at Champney’s mahogany bar. Sip a cocktail by the fire and dine on the restaurant’s creative, locally sourced cuisine.
Boston, MA
XV Beacon
15 Beacon Street 617-670-1500Walkable and welcoming, Boston is a delight in the winter, and this hotel is in the heart of it all
Crisp ocean air, snow glistening on cobblestoned streets, cozy restaurants: Boston, MA is an exceptional city for wintertime visits, and in the heart of it all is XV Beacon in its turn-of-the-century Beaux Arts building. The boutique hotel is central to all that makes wintertime fun in the city: theaters, sports venues, boutiques, galleries and museums. All hotel rooms, suites and studios have gas fireplaces and luxurious bedding, including cashmere throws. Some have whirlpool tubs, and four-poster or canopy beds. An experienced concierge can help with tickets, tours, recommendations for restaurants as well as jogging and walking routes. Steps from your hotel room is Mooo.... Beacon Hill restaurant, a favorite gathering place for guests and Bostonians on a cold winter night. Ask about the hotel’s Winter Wishes package.
Rowley, MA
Briar Barn Inn
101 Main Street 978-653-5323Warm and welcoming, this North Shore inn, spa and restaurant offers a relaxing winter escape
With its many warm and inviting spaces, the Briar Barn Inn is the perfect retreat for your winter getaway. All of the inn’s 30 distinctive guest rooms have gas fireplaces and cozy seating areas, original artwork, custom furnishings, plush robes and bathrooms with large soaking tubs. Make it a truly relaxing getaway with a massage, facial or other body treatment at The Spa at Briar Barn Inn. Or, enjoy the many winter activities on the vibrant North Shore, from snowshoeing and cross-country skiing to antiquing, brewery-hopping or shopping in downtown Newburyport, MA. At the inn, dine in the post-and-beam barn restaurant, Grove, for dinner or weekend brunch. Add “The Briar” package to your room, and signature chocolate chip cookies and wine will be waiting for you upon arrival.
Marblehead, MA
Harbor Light Inn
58 Washington Street 781-631-2186Take a break from winter, or embrace it, with a visit to inviting harbor district inn
Marblehead, MA, on the scenic North Shore of Massachusetts, is especially lovely in the winter, and you can see the town to its best advantage from the popular Harbor Light Inn. Located in the Harbor District, the bed-and-breakfast inn is a short stroll to shops, restaurants, galleries and homes that date back to the 17th, 18th and 19th centuries. Take a drive out to Fort Sewall and walk a bit for gorgeous harbor views, or drive to the many museums and attractions in nearby Salem, MA. At the inn, enjoy a continental breakfast buffet each morning, sweet treats and beverages in the afternoon, and wine, beer, cordials and bar bites in the evening in the cozy tavern. Rooms have options including fireplaces, two-person jetted tubs, exposed beams and private decks or patios.
Salem, MA
Salem Waterfront Hotel
225 Derby Street 978-740-8788Waterfront hotel and historic Salem welcome visitors warmly in the winter months
The Salem Waterfront Hotel & Suites welcomes you in the winter – and so does its vibrant city. Get cozy in your luxurious room or suite, swim in the heated indoor pool, work out in the fitness center or dine in the pub. Then set out to enjoy Salem in the winter, with its quaint colonial structures, and shops, all decked out in lights and holiday decor. Start in the hotel’s neighborhood – Pickering Wharf – a lovely harborside “village” of shops and restaurants. Then head downtown to visit the extensive art collections at the Peabody Essex Museum. Visit Nathaniel Hawthorne’s House of the Seven Gables or one of the many attractions devoted to Salem’s witch-y history. The area has a variety of winter festivals, strolls and house tours.
The Berkshires Region, MA
Visit the Berkshires of Western Massachusetts
413-499-1600Whether winter means recreation or relaxation, the Berkshires has a getaway just for you
Are you the kind of person who can’t wait for winter so you can explore the frosty outdoors? Or is winter something that makes you want to curl up by a cozy fire? Whichever type of winter person you are, you’ll find the perfect getaway in the Berkshires. During cold weather the region boasts alpine and cross-country skiing, snowboarding, snowmobiling, skating, and ice fishing. It also serves up some lovely fireplaces — in your room at a charming country inn, or in a romantic restaurant with mountain views. Book a massage in one of the area’s many spas and wellness centers, visit an art museum or lovely historic home, take an art class, catch a play or concert, or explore the offerings in a winery or brewery. The Berkshires cannot wait to welcome you!
Shelburne Falls, MA
Shelburne Springs
904 Mohawk Trail, 413-512-1454Elegantly restored mansion close to Berkshires’ best winter attractions
Shelburne Springs is an ideal base for a winter getaway in the Berkshires. This elegantly restored inn offers seven designer suites, cozy common spaces, and a grand stone fireplace lounge — everything you need to unwind after a full day of winter adventure. The surrounding region delivers some of New England's best cold-weather activities, from skiing and snowboarding at Berkshire East to snowshoeing, ice skating, and scenic winter hiking. When the day is done, return to the warmth of the inn, gather around the outdoor fire pits, and take in the peaceful beauty of the snow-covered grounds. A perfect winter retreat.
Hancock, MA
Huttopia - Berkshires
312 Kittle Road, 413-343-8192A Magical Winter Escape Surrounded by Nature
Experience the magic of a Berkshires winter at Huttopia Berkshires with our four seasons Sierra Tiny Houses. These specially designed accommodations feature full heating systems, cozy wood stoves and private fire pit for authentic winter ambiance. Wake up to snow-covered mountain views of Jiminy Peak, perfect for winter sports enthusiasts. Each tiny house offers complete amenities including full kitchens, bathrooms, and comfortable sleeping for up to 5 guests. Access winter activities like skiing at nearby Jiminy Peak, snowshoeing through pristine forests, and cozy evenings by the fire. Our heated facilities and winter-ready infrastructure ensure comfort throughout your cold-weather retreat in the beautiful Berkshires.