11 Charming Massachusetts Towns For The Perfect Getaway
Breathtaking landscapes, historical marvels, and a wide range of architectural styles are only a few reasons that make Massachusetts so unique. Between Provincetown's cultural and artistic wonders, the world-renowned storied landmarks of Salem, the intriguing beach phenomena of Manchester-by-the-Sea, and the remarkable harbors of Rockport, a trip to The Bay State will captivate your heart. Discover some of the most charming Massachusetts towns for the perfect getaway today!
Provincetown
At the northern tip of Cape Cod, Provincetown is a small picturesque town that makes for an incredible escape. Whether you are here for beautiful beaches like Race Point, known for its spectacular sand dunes and whale watching opportunities, or exquisite art galleries, including the 100-plus-year-old The Provincetown Art Association and Museum, featuring more than 3,000 works of art, Provincetown is undoubtedly one of the most charming Massachusetts towns for the perfect getaway.
The town has even become a favorite amongst the LGBTQ+, holding lively parades and special weekends to celebrate diversity, as well as gay-friendly bars on Commercial Street. A wide range of accommodations are available, from cozy guest houses to luxurious boutique inns. The Brass Key Guesthouse is a lovely place to stay in the heart of the city; various room styles are available here.
Stockbridge
Welcome to Stockbridge, one of the most charming Massachusetts towns, for the perfect getaway. Between the culture-packed attractions of Main Street, including the colonial-era Mission House (a National Historic Landmark with its marvelous exhibit and garden), and the fairy-tale-like landscapes of Prospect Hill, where the Gilded-age style Naumkeag museum stands, history buffs and architectural enthusiasts will be in for quite an adventure.
Discover vibrant florals and diverse plants as you meander through the 24-acre Berkshire Botanical Garden, one of the oldest botanical gardens in New England. Make sure you visit the Norman Rockwell Museum, seeing the original paintings of the legendary American painter and illustrator in the town he called home for 25 years. Stockbridge Country Inn can be reached within a two-minute drive or a 20-minute walk from here. Enjoy full-service country breakfast in this cozy inn, choosing from multiple room and suite styles.
Newburyport
Get a great taste of New England in Newburyport. This captivating coastal city is rich in architectural styles, ranging from Greek Rival to Mid-Century, Colonial, and many more. Explore the intriguing mix of structures as you wander through the quaint downtown streets filled with dining and shopping opportunities. See the stunning florals of Maudslay State Park, a wonderful spot for hiking, biking, horseback riding, and cross-country skiing.
Bask in the beauty of Parker River National Wildlife Refuge, where gorgeous water views and fascinating creatures await. The historic Plum Island Lighthouse is also an extraordinary sight to see. First lit in 1788, this magnificent site was also the 13th lighthouse constructed in America. A few minutes drive or 40-minute walk southeast will take you to Blue - Inn on the Beach for a luxury cottage beachside experience.
Nantucket
Soak in the coastal magic and small-town vibe as you escape to the gorgeous island community of Nantucket, one of the most charming Massachusetts towns, for the perfect getaway. Capture mesmerizing views from Brant Point Lighthouse, listed on The National Register of Historic Places. Its current structure has lasted since 1856.
Sit back and sip on craft beers in Cisco Brewers; live music nights and trivia events regularly take place here. Get sun-kissed on Jettie Beach, where the surf is calm and the water is warm. Cliffside Beach Club is a lovely spot to stay close to the beach; its incredible location is only one mile from the town center.
Williamstown
Experience the old-fashioned charm of Williamstown, where exquisite art galleries come together with picturesque natural sights. Whether you prefer the artistic wonders of the Clark Art Institute, featuring a wide range of exhibitions, collections, publications, and arts on the grounds, or the jaw-dropping landscapes from Mount Greylock, the state’s tallest peak, you will quickly fall in love with this captivating town.
Field Farm Reservation offers eye-catching views within the Berkshires and a serene stay in the Field Farm Guest House. This mid-century modern Bed and Breakfast will take you back in time with its period artwork, extraordinary architecture, and spectacular sculptures.
Manchester-by-the-Sea
Approximately 30 miles north of Boston, you will find Manchester-by-the-Sea. Renowned for its stunning shorelines, New England-style cottages, and abundant fishing opportunities, this quaint seaside city is one of the most charming Massachusetts towns for the perfect getaway. Lay back and relax, surrounded by the powdery sand on Singing Beach. Named after this fascinating natural phenomenon, listen to the unusual noises the sand makes as you walk over the dry upper portion of the beach. Search for all kinds of treasures in Manchester By the Book, its books ranging from fiction to history, art, and religion. Study the restored period rooms, sculptures, paintings, and exhibits in Manchester-by-the-Sea Museum, set in the 1823 Abigail Hooper Trask House.
A 15-minute drive northeast will take you to the Ocean House Hotel at Bass Rocks. Listed on the National Register of Historic Places, this extraordinary hotel on the shores of Cape Ann offers jaw-dropping views of the Atlantic Ocean. Enjoy its cozy amenities, including the hot tub, heated outdoor pool, and complimentary breakfast.
Oak Bluffs
Speaking of island communities, head to Martha’s Vineyard to explore one intriguing town. Oak Bluffs, originally named “Cottage City,” welcomes visitors with its beautiful beaches, picturesque parks, and notable attractions such as the Flying Horses Carousel, the oldest platform carousel in the US. Find a slice of paradise on Joseph Sylvia State Beach, strolling along its scenic shoreline and swimming amid the gentle waters. Ocean Park is a lovely spot to explore, where fireworks displays and seasonal festivals take place. Morgan Hotel is right nearby. Stay someplace surrounded by history, with its mid-century furnishings and exquisite Victorian architecture.
Sturbridge
Experience the true magic of New England in Sturbridge, one of the most charming Massachusetts towns, for the perfect getaway. Explore the recreated 1830s town of Old Sturbridge Village, where over 40 historical buildings can be found. Head on a picturesque walk through Wells State Park, an incredible spot for horseback riding, cross-country skiing, hiking, and mountain biking. Walker Pond is also filled with fish, from Largemouth Bass to White Berch and pumpkin seed. Sit back and sip on craft beer at Altruist Brewing Company, where the atmosphere is warm and inviting. A three-minute walk east will take you to Sturbridge Country Inn. This cozy hotel offers clean and comfortable accommodations in the heart of the city.
Gloucester
Are you still wondering where to go on vacation in Massachusetts? Gloucester is an incredible destination. Recognized as the oldest seaport in America, established all the way back in 1623, the city is teeming with maritime history. Learn about its past and heritage in Maritime Gloucester, exploring Gorton's Seafoods Gallery and the Maritime Science Education Center.
Capture striking photos of the Eastern Point Lighthouse, established in 1832.The views of the Cape Ann Coast are genuinely spectacular from here. Hammond Castle Museum is another site you can not miss. Discover fairy-tale landscapes from this medieval-style castle, where interactive exhibits, theatrical performances, educational programs, and activities for the whole family are held. Nearby, The Hydrangea Inn offers a cozy stay with complimentary continental breakfast, Cable, Wi-Fi, and views overlooking the Gloucester Harbor.
Rockport
If you are a fan of enchanting harbors and stunning art galleries, such as The Rockport Art Association & Museum, with its one-of-a-kind exhibitions, then you have come to the right place. Spend some time by the rocky coast in Halibut Point State Park. Explore the scenic trails and tidal pools; you may spot sea creatures such as Sea Stars, Hermit Crabs, and Harbor Snails.
Pay a visit to the Paper House, a magnificent structure that was actually built from paper by Mechanical Engineer Mr. Elis F. Stenman in 1922. Closer to the coast, you will find Emerson Inn By The Sea, an excellent oceanfront hotel offering memorable accommodations on Pigeon Cove.
Salem
Known as the place where the 1692 to 1693 Witch Trials took place, Salem is steeped in history. Learn about the city's dark past in the 17th-century Witch House (aka The Jonathan Corwin House), including how the trials began and were brought to an end. Another famous site is The House of the Seven Gables.
This remarkable 1668 home, designated a National Historic Landmark District in 2007, inspired American author Nathaniel Hawthorne’s renowned 1851 novel. History buffs can dive into over 600 years of New England's maritime past and relations in the Salem Maritime National Historic Site. This legendary site was established in 1938 as the first National Historic Site in the United States. You can stay in Morning Glory Bed & Breakfast, a well-resorted 1808 Georgian Federal heritage home within walking minutes of these significant landmarks.
Embrace the Unique Allure of Massachusetts' Towns
Between breathtaking beaches, renowned historic landmarks, and an intriguing mix of architectural styles, The Bay State is filled with quaint New England towns that make for an incredible escape. Whether you prefer the historical botanical gardens of Stockbridge, the legendary centuries-old lighthouses of Nantucket, or the scenic hiking trails of Williamstown, you will find relaxation and fascinating new adventures. Choose from these 11 charming Massachusetts towns for the perfect getaway.
