9 Romantic Getaways in New England for Every Kind of Couple

Romance is a concept as complicated as the couples who define it. Yet one thing is certain: some of the most romantic getaways are in charming New England, from quaint Kennebunkport’s annual celebration of love to Newport’s romantic hotels. Craving a staycation rendezvous in Boston? Or a cozy retreat in Woodstock, Vermont? Whatever the mood calls for, New England has it, and these curated itineraries are sure to set hearts racing.

Here, find 9 destinations that make for the most romantic getaways in New England.

Kennebunkport, MaineThe Kennebunk River in Kennebunkport.Photo: Getty Images

While Kennebunkport is charming year-round, February brings a month-long celebration of love, transforming this coastal town into an amorous wonderland for its Paint the Town Red celebration. Give into the Valentine’s Day spirit as shops, restaurants, and accommodations all partake in the festivities, offering romance packages, special dining experiences, and red tag sales. Stay at the Kennebunkport Inn or the White Barn Inn. Take a wine and cheesing pairing class at White Barn’s wine cellar, or pick up a box of hand-selected artisanal cheeses and charcuterie from The Port Box Company, and relish a day of antique shopping. Treat yourselves to Sunday brunch at Via Sophia by the Sea and dinner at Chez Rosa, an intimate French bistro in a barn setting (open Wednesdays through Sundays).

Bar Harbor, MaineWooden storefronts in Bar Harbor, Maine.Photo: Getty Images

Bar Harbor, an entry point to Acadia National Park, is the ideal low-key retreat, with its mountaintop vistas and adventurous ambiance. If you’re not an outdoorsy duo, there are plenty of shops and galleries to keep you busy. Book a guest room at the bed and breakfast Yellow House Inn or the Bar Harbor Inn for accommodations boasting ocean views. (If this is a really special occasion, The Bayview Hotel offers an elopement package.)

Litchfield County, ConnecticutThe Housatonic River Valley in Litchfield County, Connecticut.Photo: Getty Images

In 2021, Vogue called Litchfield County, Connecticut “the perfect weekend getaway.” Almost four years later, it’s somehow only gotten better: this September, boutique hotel The Abner opened right in Litchfield town, and come March, they will be joined by the Belden House & Mews. The highly anticipated property will span three buildings—an 1888 mansion, a 1960s modernist structure, and the old Litchfield Firehouse. For those looking for a country retreat, the bucolic Mayflower Inn in Washington is set upon 58 acres and includes walking trails and a world-class spa.

The town of Bantam is also a must-visit thanks to Arethusa Farm, a working dairy farm run by two former Manolo Blahnik executives that operates three delicious eateries in town: The first is the restaurant Arethusa al Tavolo, which serves “seed to table” cuisine. Then, there’s their breakfast and lunch café Arethusa al Mano. They offer homemade doughnuts—cinnamon! cold brew! Bantam cream!—and a special cookie of the month. Finally, their ice cream and dairy shop offers gourmet scoops as well as seasonal eggnog.

Boston, MassachusettsAcorn Street in Boston, Massachusetts.Photo: Getty Images

The city of Red Sox and lobster rolls doesn’t always feel synonymous with romance, but with the right itinerary, the city offers an unforgettable getaway (or staycation). Stay at The Beacon, whose Library Bar and rooftop restaurant Contessa are by Mario Carbone’s Major Food Group. Although if you want to venture out, do so for a hearty Italian meal in the North End or at Beacon Hill’s No. 9 or 1928.

As for what to do? Wander the Isabella Stewart Gardner Museum, which was modeled after a Venetian palazzo. Their collection includes Vermeers, Rembrandts, Manets, and Singer Sargents. Then, buy tickets to a Red Sox game at Fenway Park—the oldest baseball stadium in America.

Lenox, MassachusettsAutumn leaves along a lakeshore near Lenox, Massachusetts.Photo: Getty Images

Nestled in the heart of the Berkshires, small-town Lenox is ideal for couples seeking a mix of nature and culture. Book a stay at 33 Main or Lifehouse for an in-town experience, or head to Miraval or Canyon Ranch for a wellness-focused vacation. Hit the shops on Main Church Street—including MacKimmie Co, known for their cashmere blankets—before heading to Edith Wharton’s former home, The Mount.

As for dinner and drinks? Firefly is a perennial favorite, whereas Apple Tree Inn’s Ostrich Room offers live music.

Woodstock, VermontSunset over the Green Mountains above Woodstock, Vermont.Photo: Getty Images

Skip the crowds in Stowe and head to Woodstock, a destination that elevates winter romance with a plethora of adventures. Try snowmobiling for the first time, hire a snowshoe guide, or take a ski lesson at Saskadena Ski Resort. Reserve a room at the Woodstock Inn & Resort, and after a day in the snow, relax at the inn’s Spa; breathe in the sauna, unwind in the whirlpool, and pamper yourselves with the Signature Experience.

Portland, MaineThe Portland Head Lighthouse looking out over Casco Bay. Photo: Getty Images

Vogue has an extensive guide to Portland, Maine, but we will share an abridged version here: stay at the newly-opened Longfellow Hotel or The Blind Tiger, and get lobster rolls at The Highroller Lobster Company. (If you’re sick of seafood, noodle bar The Honey Paw is run by James Beard award-winning restauranteurs.)

Journey to the Portland Head Lighthouse, or out to sea with the Lucky Catch Cruises, which allows you to catch your own crustaceans.

Newport, Rhode IslandRosecliff Mansion Museum.Photo: Getty Images

The holiday season is arguably the most alluring time to visit Newport. See “The Newport Nutcracker” ballet at Rosecliff Mansion, originally built in 1902 for heiress Theresa Fair Oelrichs and her lavish Gilded Age events. The city also boasts an array of wineries and breweries for you and your loved one to explore. For lodging, choose Castle Hill, The Vanderbilt, The Chanler at Cliff Walk or the recently opened Gardiner House.

Nantucket, MassachusettsPhoto: Getty Images

There is perhaps no more famous New England getaway than Nantucket, Massachusetts—the quaint island and former whaling town that inspired Herman Melville’s Moby Dick. Once you visit, you’ll understand why, with its cobblestone streets, mom-and-pop shops, sandy beaches, and distinctive “Nantucket gray” shingled homes. Summer is the high season—where lines for the Juice Bar stretch far out the door—but it also has plenty of year-round charm: Vogue wrote a whole guide to the island in the fall, whereas December is famous for its Christmas stroll. Stay at The White Elephant or The Summer House, and fall in love with the whaling town the way so many have before.