There’re excellent places to stay in Massachusetts — on top of Boston. For a trouble-free trip during the warmer months of the year, consider the quaintly floating Martha’s Vineyard and Nantucket, two of the USA‘s most classic summer getaways. If you plan on taking a fall trip, seek inspiration in the nature-meets-art Berkshires.
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Experience history along the 2.5-mile (4 km) Freedom Trail, tying 16 spots of national significance together. A sweet sample? Old South Meeting House is where the 1773 Boston Tea Party started, resulting in the storied dumping of 342 tea chests.
Stay in Downtown Boston to have that unique trail at your fingertips. However, while it’s the most convenient location for sightseeing, there’re several other lovely Boston neighborhoods to choose from.
Back Bay, with the elegant Newbury Street leading the way, is for the shopping lover. Dive into an appreciated mix of shops — think everything from upscale brands to budget-friendly merchandise — before sitting down for coffee at a trendy coffee hangout.
As charming, at least, Beacon Hill is home of Boston’s most quintessential cobblestone alleyway, Acorn Street. Yet the good looks is just the start: Browse boutiques on Charles Street and discover the Black Heritage Trail, teaching about the abolitionist movement.
You don’t have to go down to Florida to find gorgeous, seemingly endless beaches. Instead, immerse yourself in the coastline environment of the hook-shaped Cape Cod, reaching 65 miles (105 km) into the Atlantic Ocean.
A crown jewel, Cape Cod National Seashore on its own features 40 miles (64 km) of beaches. Spread out a towel and recline; if you want to get active, explore trails taking you through woods and past ponds.
Where amid this sandy pleasure should you stay? Charming seaside towns spread out all across Cape Cod, but for access to Cape Cod National Seashore, bed down in Chatham, Orleans, Eastham, Wellfleet, Truro or Provincetown.
How to get there? It’s only a 1-hour drive from Boston to the beginning of Cape Cod, connected to mainland Massachusetts by two bridges spanning Cape Cod Canal.
Miss the summer camps from your childhood days? Or maybe you never got to experience that kind of summer adventure, filled with whimsical but at the time important-feeling activities, and want to make up for it now?
Head to Martha’s Vineyard, floating a 35-minute ferry ride off Cape Cod, and let its untroubled vibe wash over you.
Oak Bluffs, one of six island towns, is dotted with 300-plus gingerbread cottages in vibrant colors, originally built in the 1860s and 1870s for summer camps. To fully engage in that summer camp dream, make the unique, playful Summercamp hotel your base.
While touring the island, keep an eye out for Jaws spots — the 1975 movie was filmed here. Make sure to stop in the refined Edgartown, characterized by bone-white ship captain’s homes from the time when the Vineyard was a key player in the whaling business.
Salem has a dark side, one that makes it a popular option for where to stay in Massachusetts especially around Halloween (book early). Also called Witch City, this place used to be full of intolerance and injustice — deadly such.
Take the self-guided Salem Witch Trials Walk of the Peabody Essex Museum to learn about the 1692-93 Salem Witch Trials, during which 200-plus people were accused of witchcraft, leading to 19 executions and at least six other deaths (under torture and in jail); it encompasses both exhibits inside its galleries and historic sites around town.
Walking the streets, you can’t help but notice the abundance of witch-related attractions, magical stores and spooky tour options that form Witch City. While the past is chillingly dark, Salem embraces it.
To be surrounded by this occult madness, check in at one of the cute hotels in the compact Downtown Salem. Pro tip: Garlic is said to keep witches (but maybe also loved ones) away.
This “other cape” doesn’t present a vast coastline or long list of towns (like Cape Cod). Instead, appreciate a compact collection of rocky cliffs, soft beaches and historic buildings proving just how nice a smaller scale can be.
You quickly fall for the classic New England setting of the easternmost town, Rockport. Join locals and fellow visitors on Bearskin Neck, a salty land strip sheltering the harbor from the open ocean and providing independent shops and delicious seafood eateries.
Neighboring Gloucester may lack the quaintness of Rockport but makes that up by offering Cape Ann’s best beaches; catch some rays on the southern Good Harbor Beach or northern Wingaersheek Beach.
What makes this option for where to stay in Massachusetts even better is the convenience. You can drive from Boston to Cape Ann in under 1 hour; if you don’t have a car, take advantage of the train connection.
Hop aboard a high-speed ferry in Hyannis, Cape Cod, and one hour later, you arrive on Nantucket. Welcome to a timeless Massachusetts island feeling refreshingly far away from the everyday hustle and bustle.
Nantucket Town, where the ferry docks, is the main population center. Bed down in this cobblestoned dream to have all you need within walking distance: Restaurants, shops and the beach — that’s handy.
But if you really want to escape it all, opt for one of Nantucket’s (even) smaller villages, the kind of places that you bike through in minutes. A romantic luxury hotel, the Wauwinet presents a breathtaking northeastern location where Nantucket Harbor meets the Atlantic Ocean.
Central Massachusetts & Connecticut River Valley
Want to dodge the tourist trail altogether? With salty coastal Massachusetts to its east and rising Berkshires to its west, the glueing areas of Central Massachusetts and Connecticut River Valley (also called Pioneer Valley) fly under the radar.
Yet Springfield, MA, has excellent museums: Dive into The Amazing World of Dr. Seuss Museum, with an interactive first floor (perfect for kids) and adjoining sculpture garden, or see if you still got it at the Naismith Memorial Basketball Hall of Fame, a mecca for sports lovers.
Adding life and ambition, proud colleges scatter the region: Amherst is built around the gigantic University of Massachusetts but also features Amherst College and Hampshire College, while the eclectic neighbor Northampton hosts one of the most influential women’s institutions in America, Smith College.
Picture lush highlands laced with winding roads and dotted with culture-filled towns. There you have it: The idyllic, picture-perfect Berkshires region, covering the most western slice of Massachusetts and some of neighboring Connecticut.
Bags packed and ready to go already? Wait, where exactly should you go?
Stockbridge makes a painting-like base for where to stay when visiting The Berkshires. Norman Rockwell — America’s favorite illustrator — lived here for 25 years and used his home town as inspiration (including fellow locals). Visit Stockbridge’s Norman Rockwell Museum to judge the celebrated artworks yourself.
Lenox is another leafy Berkshires town brimming with inspiration. Step into the Mount Home, where iconic writer Edith Wharton once lived. Marvel at the imposing mansion, a National Historic Landmark, and be engaged by Wharton’s life story.
Looking for where to stay in Massachusetts to enjoy fall foliage? Williamstown sits at the western end of the Mohawk Trail, a bucket-list road trip for leaf peepers; for the full drive, begin your journey in Westminster.
Where to stay in Massachusetts FAQ
Boston may be the most popular option for where to stay in Massachusetts, but there’s something for every visitor and mood. Also consider Cape Cod, Martha’s Vineyard, Salem, Nantucket, Central MA & Connecticut River Valley and The Berkshires for your next Massachusetts getaway.
A blend of New England and Harry Potter, Salem embraces its dark past with haunted happenings. Check in at the atmospheric Merchant, Hawthorne Hotel or Salem Inn to experience the unique vibe first hand.
The nature-meets-art region of the Berkshires occupies western Massachusetts. Choose from an array of gorgeous towns, including Stockbridge, Lenox and Williamstown.
You find stunning fall foliage all over the Berkshires. However, Williamstown stands out as the westernmost end of the legendary Mohawk Trail drive, showcasing stunning fall colors.
Don’t look past Salem for where to stay over Halloween. While this town, nicknamed Witch City, offers a Halloween vibe year round, it all peaks in October when special haunted happenings take place.