8 Beautiful Places in Massachusetts Beyond Boston

The most beautiful places in Massachusetts span far beyond Boston. Here's a list of the best locations for your next gorgeous getaway.

Massachusetts may be one of the smallest states in the country, with most of its population centered around the capital, but the Bay State is home to a disproportionate share of beautiful places that span well beyond Boston. From the numerous beaches lining the bays of the more bustling east to the mountains and valleys anchored by the Connecticut river in the rural west, New England history and heritage continue to inspire grace and beauty in every corner of the state.

Before planning your next getaway, take a look at the list below for an introduction to some lesser known stunners across the state, as well as some new ways to appreciate a couple of old favorites. For the total package, don’t forget our accommodation tips to perfectly complement each of these beautiful places in Massachusetts.

Go Beyond the Velvet Rope in Lenox

You can tour historic homes around the world, but you can’t go much farther than the velvet rope across the doorway to see many period-decorated rooms within. This is not the case at The Mount, the mansion and gardens designed by American author Edith Wharton in Lenox, Massachusetts.

Not only can you fully enter the rooms here, but you’re invited to use the replicated furniture within and truly experience what a literary icon’s daily life was like here. Take a poke around the library, one of Wharton’s favorite rooms, and see what (and who) inspired the words that have inspired so many since.

Outside, the formal gardens are a bit simple, but no less refined than the rest of The Mount, and well worth a stroll. For an even deeper dose of high culture, check out Tanglewood, the Boston Symphony Orchestra’s summer home, and Shakespeare & Company, both also in Lenox.

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Our accommodation tip:

Of all the furniture you can use at The Mount, you can’t climb under the covers of the beds, but you can still sleep in period style at Hampton Terrace Inn. Built in the 19th century, this sophisticated bed and breakfast became an inn in 1937, when the orchestra first came to town, and today retains its Gilded Age glam alongside plenty of modern updates (try the Jacuzzis inside and the heated pool outside). The Inn is centrally located to all of Lenox’s top venues, but there’s a chance you’ll catch a live performance without leaving the property—if anyone in residence during your visit plays piano (including you!), the antique 1929 Steinway is tuned and ready to resound.

Hampton Terrace Inn

8.9 Excellent (217 reviews)

Explore a European Castle Stateside in Gloucester

There are plenty of castle-like homes and buildings across the country, but few resemble the real medieval masterpieces strewn across Europe. Hammond Castle is an exception, and you’re welcome to explore its many fascinating rooms in Gloucester, Massachusetts.

Now a museum, this hodgepodge of architecture contains castle elements from multiple centuries and was custom built to house the massive art and artifact collection of successful inventor John Hammond Jr. in the 1920s.

Today, you can also explore exhibits on the life of Hammond and his many inventions. However, the house itself remains the main attraction, despite the priceless collection within. Get ready to live your wildest historical fantasy—there are more gothic arches and thick red curtains than you can count.

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While you can’t sleep in the castle on the bluff, you can still score a waterfront room and get the royal treatment at Beauport Gloucester less than 10 minutes away. Gloucester is home to America’s oldest fishing port, so expect plenty of nods to the nautical life, all with sophisticated New England style. Especially appreciated by families and corporate retreat visitors, the large property boasts a rooftop pool and the onsite 1606 Restaurant, though the menu skews heavily toward a more refined palate (even the burgers), so those with younger children may want to head into the quaint downtown area for most meals.

Beauport Hotel Gloucester

Top rated
9.6 Excellent (1335 reviews)

Pick Your Peak and Enjoy the View in Deerfield


Deerfield’s Mount Sugarloaf may not be the tallest point in the state, but its dramatic cliffs and relatively easy ascent draw plenty of visitors looking for reasonably accessible views of the surrounding Connecticut River Valley.

There are two summits here, interchangeably called Mount Sugarloaf by various entities, and you can hike either one for similar views, but the south summit is more developed. Seasonally, the south summit can be reached entirely by vehicle if needed, but you can hike it year-round (it should only take about an hour in clear conditions). In season, step into the observation tower atop the south summit for an even higher view of the landscape.

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Head about 20 minutes northwest to Shelburne Falls for a stay in Shelburne Studio. This private studio apartment comes complete with a private entrance,  a modern bathroom, quaint deck seating for morning coffee or evening drinks, and a small kitchenette with a microwave, stovetop, and fridge. If you’re here in warmer months, take advantage of the opportunity to check another one of Massachusetts’s most beautiful places off your list with a walk across the Bridge of Flowers. This charming arch bridge was once a trolley crossing and is now a free pedestrian garden spanning the Deerfield River.

Newly Remodeled Shelburne Studio

Shelburne Falls
10.0 Excellent (170 reviews)

Find Your Fairy Tale in Martha's Vineyard


Martha’s Vineyard has long been a popular getaway for the society set, but one neighborhood in particular warrants a visit from everyone.

The Oak Bluffs area is positively overrun by fanciful Victorian cottages decked out in vibrant collars and drowning in gingerbread detail on every surface, from porches and trellises to window frames and roof trim. All told, there are 318 of these spectacles in this neighborhood alone, making it a wonderland of fairy tale fantasy that’s as engaging for kids as it is impressive for adults.

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Also located in Oak Bluffs, Isabelle’s Beach House is a handsome bed and breakfast on Nantucket Sound with cottage décor and an Adirondack-packed oceanfront porch that provides all the Martha’s Vineyard vibes you came for, day or night. Enjoy the views with a morning muffin, an evening sip of complimentary wine, or both while unwinding from strolls around the colorful neighborhood. A full breakfast is also provided, as well as freshly baked cookies in the afternoon.

Isabelle's Beach House

Top rated
Oak Bluffs
9.4 Excellent (48 reviews)

Get Hands-On with History in a Historic Village


No mere shopping street or small group of preserved historic homes, Old Sturbridge Village is an entire 1830s town reborn to its original splendor.

The largest outdoor history museum in the Northeast, stroll the streets and paths among 40 original buildings dating back nearly 200 years, all with a bucolic New England backdrop that’s equally evocative in all seasons. The past lives on here with costumed historians recreating the scene of a once bustling village, while heritage breed farm animals roam the fields and pastures surrounding the shops, mills, bank, church, and school.

Whichever aspect of early American village nostalgia appeals to you most, you’ll find it here. Plus, you don’t have to be a history buff to love it: the village itself is a splendid setting for a leisurely stroll, and the 200-acre property also includes nature trails, gardens, and riverbanks for simply appreciating nature on a beautiful day.

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Reacclimate to the current day by checking in to Southbridge Hotel & Conference Center inside the restored 19th-century red brick factory originally built to house the American Optical Company. The sprawling space (seriously, you can’t miss it) may not have “resort” in the name, but everything you want from resort living is here. Eat your fill at the onsite restaurant or lounge, sip cocktails by a fire pit on the patio, and work it all off with free classes in the fitness center and indoor pool before de-stressing in the sauna. Bonus: If you’re in town for work, there are 24,000 square feet of high-tech meeting spaces here, perfect for combining business with pleasure.

Wellsworth Hotel

Top rated
9.0 Excellent (2072 reviews)

Get Corny in Sandwich


The entire Town Square Hall Historic District in Sandwich exudes the slow charm of yesteryear, but the most idyllic scene can be found at the Dexter Grist Mill. This 17th-century mill is among the most photographed landmarks on all of Cape Cod and is still operable, producing corn meal sold in cloth sacks that you can bring home as a functional souvenir (recipes included!).

Surrounding the mill are the quiet Shawme Pond, stately Town Hall, and plenty of Colonial houses. Be sure to walk the short distance to Hoxie House to tour the authentically restored 1640s home that remains the most famous in Sandwich, crowning the picturesque district from its perch above the pond.

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Our accommodation tip:

Embrace a simpler lifestyle for your time in Sandwich. Take your pick from motel rooms or individual cabins at Sandwich Inn & Suites; either way, you’ll have a private entry leading directly to the outdoors and simple yet comfy interiors to refresh and recharge before exploring further. This low-frills property is particularly ideal for families, with laundry and vending facilities near the lobby. The complimentary breakfast, offering high quality ingredients alongside organic coffee, is worth noting.

Sandwich Inn and Suites

9.2 Excellent (1422 reviews)

Dip Your Toes in the Country's Most Famous Pond


Jump right in for a dip at Walden Pond right outside of Henry David Thoreau’s famous one-room cabin.

Depending on the season, it may be too cool to actually want to swim here, but the pond is ringed by a 1.7-mile hiking path that’s charming year-round. In warmer months, you can enjoy the calming waters of this glacial kettle pond by boat or paddle board – you’ll need to bring your own equipment as there are no rentals within this state reservation.

The original location of Thoreau’s cabin is marked along the pond path and the hearthstone of his self-constructed cabin remains in place, but you may have trouble reaching it in winter months. The more popular replica, complete with a Thoreau statue, is located by the reserve’s parking lot, and will give you an even greater understanding and appreciation of his two years here.

If your time at Walden Pond State Reservation piques your literary curiosity, pop over to Louisa May Alcott’s Orchard House, also in Concord, to ogle the gorgeous property that was both home to the author and the setting of Little Women.

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Continue the philosophical and scholarly themes of your natural escape with a stay at Hawthorne Inn. This 19th-century bed and breakfast was built on property previously owned by Ralph Waldo Emerson, the Alcotts, and Nathaniel Hawthorne, making it perhaps the most literary land in America. Elegantly appointed with modern conveniences and high-end textiles and furnishings, Hawthorne Inn takes a natural approach to luxury with décor and design that inspire without losing sight of the surrounding environment that inspired the entire Transcendentalism movement.

Hawthorne Inn Bed & Breakfast


Listen to the Cape Cod Waves Crash by the Bonfire


All of Cape Cod’s shorefront is designated as a national seashore park and you’d have no trouble locating dreamy vistas anywhere along the peninsula. However, Race Point Beach is a must-stop for quintessential seaside beauty. During the day, stroll the wide sands stretching from dunes to shore and be sure to round the point to admire the romantic Race Point Lighthouse, dating to the mid-19th century.

Admittedly, it’s a considerable walk across the sand to reach this point, so if you’re not up for the moderate exertion, consider acquiring a permit for driving on the beach (you need to get these in person from the permit station) or taking a guided tour around the cape with Art’s Dune Tours. If you choose the latter, opt for the sunset tour for the most vibrant views, and add on a bonfire experience – Race Point Beach is one of the most popular beach bonfire spots on Cape Cod.

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Anyone staying in Provincetown wants those coveted ocean views, and there’s no better place to find them than atop Gull Hill at Lands End Inn. This exclusive boutique stay offers 18 rooms packed with elegant character, from intricate architecture to fine art and furnishings, with generous ocean views and shoreline access just steps from the Inn. Each reservation includes a complimentary parking space at the Inn, and the downtown strip of shops, restaurants, and additional beaches is just minutes away (you could walk). In addition to the generous breakfast served on the all-weather, oceanfront veranda, complimentary snacks and beverages are available throughout the day and each evening begins with a quaint wine reception.

Land's End Inn

9.3 Excellent (49 reviews)