Best 5 Romantic Winter Weekends in New England

Write your love story’s next scene in a setting as fresh as just-fallen snow at these new or recently reimagined properties, where a dash of the unexpected turns a weekend away into a romantic odyssey. Read on for our picks for the best romantic winter getaways in New England.

Best 5 Romantic Winter Getaways in New England

Getaway Boston
Epsom, NH

If supercomputing cellphones have robbed you and your partner of downtime and a sense of wonder, count on Getaway Boston to restore both. The first in a network of properties that grew out of a Harvard Business School project, this getaway is about 90 minutes outside the city, but you won’t know exactly how to get here until an email is sent to you on the day—which is also when you find out which of the 42 well-equipped, wide-windowed, dog-friendly cabins will be your nest of warmth in the winter woods. A cellphone lockbox greets new arrivals, and you can kick off the weekend with a little wager over who’ll be first to crack it open. getaway.house/boston

Graybarns on the Silvermine River
Norwalk, CT

Once an out-of-the-spotlight refuge for celebrities like Liz Taylor and Lauren Bacall, the inn and tavern known as Graybarns has been gloriously reborn after years standing vacant. Don’t be misled by the pitchforks-turned-wall-art and reclaimed barnwood that give the inn and its six adults-only king suites a rustic look. Custom-built beds, exquisite textiles, complimentary bars, and in-room spa experiences make these private retreats as elevated as any you’ll find an hour from the heart of Manhattan. Sip coffee at the Mercantile, watch icy mist rise from the mill falls, stroll to Silvermine Arts Center’s galleries, dine fireside, linger over brunch cocktails. You’ll want to spend all of your precious “together time” right here, in this setting that has long inspired artists. 

The Inn at Kenmore Hall
Richmond, MA

Even with sugar-powdered Lenox Mountain in view, and 20 acres of fields and centuries-old forest to explore (bring snowshoes), don’t be surprised if you’re content sequestering yourselves within the magnificent walls of this 1792 mansion with its three snap-crackling fires. Scott Edward Cole is an artist and former restaurateur; his partner, Frank Muytjens, is the former head of menswear design at J. Crew. And their new home with an old soul is a shared design lab, where five comfy guest rooms are dressed in a masculine earth-and-water palette and filled with an era-spanning mix of antiques, books, art, and fine furnishings. Candlelit hearthside breakfasts are co-creations, too: Expect hearty granola, fresh-baked pastries, frittatas, smoked salmon, quiches, and seasonal fruit. For the ultimate in privacy, book the Carriage House Cottage, where Leonard Bernstein took up summer residence in his early Tanglewood years.

The Row Hotel at Assembly Row
Somerville, MA

Not all romantic winter getaways in New England have to be off the beaten path. Crave the energy of city life without the hassle of navigating an unknown urban environment? The Assembly Row development, fashioned out of a defunct 52-acre Ford assembly plant, is a must-discover destination. An easy drive or eight-minute T ride from Boston, this Marriott Autograph Collection hotel is a car geek’s dream with industrial-chic details and a pink 1959 Edsel parked out front (ask for a ride in this beauty, whether you’re checking out the new Encore Boston Harbor casino or going to a TD Garden event). “Row-mance” packages add perks like champagne upon arrival. Grab frothy coffees at Caffè Nero and walk the mile-long river path, claim a private cabana by the hotel’s indoor pool, take an on-demand fitness class, and raid the complimentary guest pantry (but save room for dinner, since you’re steps away from two dozen restaurants). 

Shelter Harbor Inn
Westerly, RI

Prosecco in hand, you’ll be drawn to sumptuous leather sofas by the light of a toasty fire in this inn’s ceiling-high fieldstone fireplace—which is practically the only feature that escaped transformation when it changed hands last year. Like an improv master creating spontaneous genius from random input, designer-to-the-stars Randolph Duke has put together vibrant, conversation-igniting interiors using furnishings from around the world as well as elements inspired by the farm estate’s coastal location and its history as a music colony. You’ll feel reconnected with your partner as you watch the snow flurries through large windows in the conservatory bar, the firelit restaurant, the top-floor spa, or, of course, your own cozy guest room. Westerly’s shops, Mystic’s attractions, and invigorating walks on the inn’s private beach are all worthy diversions. 

Let us know your favorite spots for romantic winter getaways in New England in the comments below!

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