Best Romantic Massachusetts Getaways

What are the best romantic Massachusetts destinations?

The Getaway Mavens know quite a bit about Romantic Massachusetts. We’ve been finding the best offbeat and charming places to visit in the Northeast for decades. And over the years, we’ve discovered that our readers are most interested in getaways of the romantic sort.

So, you’ll find below, our picks for Best Romantic Massachusetts destinations, which include towns for witchy, sporty, literary, maritime, and American history lovers. Find your passion with your passionate one.

Interested in the rest of New England? Discover more in Getaway Mavens Romantic New England.

For up to the minute info on MA Travel, consult the Mass Tourism website.

Acorn St on a Hidden Boston Getaway

HIDDEN BOSTON MA 

Hipster couples will want to check out these secret spots in Boston. And then bed down in the city’s newest rock ‘n roll (slightly bad-ass) boutique hotel – The Verb, right in the shadow of Fenway Park. Even Bostonians don’t know about some of these places.

Candleberry Inn backyard Brewster MA

BREWSTER – CANDLEBERRY INN

This charmer of a true Cape inn has been under new management for a few years. The new owners sure know how to provide a Romantic Massachusetts experience.

Louisa May Alcott Orchard House Concord MA
Louisa May Alcott Orchard House Concord MA

CONCORD MA

Alcott, Emerson, Hawthorne, and Thereau all lived in this rural Massachusetts town best known for “the shot heard around the world.” In fact, you can tour the home in which Alcott wrote Little Women, and meanders around Walden Pond. Even more touching – stay in an Inn that harks back to the American Revolution.

Historic Deerfield Sign
Historic Deerfield Sign

HISTORIC DEERFIELD

Are you into way, way, back American History? Do you just adore strolling down historic tree lined streets where every pre-Colonial-era home tells a story (via docents)? And how about staying right in the middle of it, in a charming antique inn? You’ll find all of this in Historic Deerfield, just a few minutes drive from Amherst MA.

Romantic Sunset Sea Crest Beach Hotel Falmouth MA
Romantic Sunset Sea Crest Beach Hotel Falmouth MA

FALMOUTH/SEACREST BEACH HOTEL

Falmouth MA, in the extreme southwest corner of Cape Cod, also encompasses the tiny burg of Woods Hole. 

But there are things to see in Falmouth as well, including a recently renovated Victorian mansion turned art museum, waterfront gardens with antique anchors as central features, and some of the country’s most awesome sunsets. Right from a newly renovated beachfront hotel resort with rates that won’t drain your bank account.

Working docks Gloucester MA
Working docks Gloucester MA

GLOUCESTER MA

Lost in all the “Perfect Storm” commercial fisheries identity is the fact that this coastal New England town was also one of America’s first Artist’s Colonies –  Rocky Neck – and what’s more romantic than that? Stay in a boutique hotel, tour the eclectic home of one of the very first professional interior decorators, and drink some great beer overlooking the fishing docks on this not-so-fishy getaway.

Suite 22 Inn at Hastings Park Lexington MA
Suite 22 Inn at Hastings Park Lexington MA

LEXINGTON MA 

How can the town that saw the first shot in the Revolutionary War be on our Romantic Massachusetts list? Well, the Inn at Hastings Park in Lexington MA, manages to merge American History with amour in the most picturesque of ways. Those who find that the stirrings our our country’s beginnings also stir their hearts will love to spend a few days in this deeply American town.

Edgartown Harbor Sunset Marthas Vineyard
Edgartown Harbor Sunset Marthas Vineyard

MARTHA’S VINEYARD, MA

This New England Island- a ferry ride from Wood’s Hole, MA, delivers on hypnotic sunrises and sunsets, exceptional beaches and intimate hideaways. Even if you aren’t president of the United States, you’ll be treated like one.

Nantucket MA Ferry in harbor with lighthouse
On Nantucket Ferry Steamship Authority

NANTUCKET

Islands are just naturally romantic, given that you’ve got to take a boat or ferry to get there. Couples with a curiosity about American Maritime and Whaling history are sure to find cerebral satisfaction in this preppy place – home to one of the best Whaling Museums in the world, and of course, the iconic Nantucket Lightship Basket. Stay at the Regatta Inn on a little side-street: what rooms lack in size are more than made up for with impeccably luxurious design.

Costumed Docents at Plimoth Plantation in Plymouth MA
Costumed Docents at Plimoth Plantation

PLYMOUTH MA

Lovers of history (and each other) will go gaga over the very first New World sanctuary for “Saints” who were religiously persecuted in Europe in the early 1600’s. In 2020 Plymouth acknowledged the 400th anniversary of the landing of the Pilgrims on Plymouth Rock – with some planned celebrations online and others canceled due to the unfortunate timing of the Covid-19 pandemic. Plymouth has rescheduled some events for 2021.

Old Lifesaving Museum, Provincetown MA
Old Lifesaving Museum, Provincetown MA

PROVINCETOWN MA

Live on the edge on this edge-of-the-world resort town. LGBT couples will find nirvana (and a whole lot of choice re: accommodations), but hetero romantics (and families) will also have a great, high-energy time at the tip-end of Cape Cod.

Whether you’re gay or straight, one of the most stylish inns to book is Carpe Diem Guesthouse, with gorgeous rooms, bountiful complimentary afternoon wine and nibbles, a fantastic breakfast spread, and the largest Moroccan Hamam on the Cape.

Adams Library at Peace Fields Quincy MA

QUINCY MA

Take a deep dive into the lives of John and Abigail Adams – the quintessential romantic Massachusetts Founding Couple of All Time – where they lived, died, and are interred together in tombs on which you can place your hands. Quincy is steeped in history, but it’s also becoming more and more a foodie destination. And – an Instagram curiosity by virtue of one of its past industries. Granite. Those with a passion for history will love it here.

Motif #1 Rockport MA

ROCKPORT MA

You live in Boston or New York, and you both long for a seaside escape with lots of fresh lobster, but just don’t want to drive all the way to Maine. What to do? Head to Rockport MASS – which provides LOTS of New England Coast charm without the hassle. Stay at Yankee Clipper Inn – favorite of many celebrities of yore – a few miles from town on a wind-whipped cliff overlooking the Atlantic. It’s as romantic as all get out.

Witch Pix Photo Studio Salem MA
Witch Pix Photo Studio Salem MA

SALEM

Are you a couple bewitched? Then head thee to Salem MA, where you’ll learn about the history of the real Witch Trials at its source. This town also plays with the theme in fun ways: dress up for photos, purchase voodoo candles, take ghost tours in the dead of night.

Didn’t find what you’re looking for above? Check out the rest of Getaway Mavens Romantic Massachusetts destinations here.

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