12 Top-Rated Weekend Getaways in Massachusetts
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Looking for a weekend getaway in Massachusetts? The Bay State is filled with places to visit that offer something for everyone. Whether you are looking for a weekend focused on history, culture, sports, or just want to relax on the beach, visitors will find a spot to explore that covers their interests.
From the Berkshire Mountains to the beautiful coastline, choose your escape in the Pilgrim State from our list of the top-rated getaways in Massachusetts.
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1 Boston, Massachusetts
Boston is the perfect blend of old and new and one of the best places to visit in Massachusetts. Centuries-old neighborhoods, a rich history, and modern skyline make this city a draw to millions of visitors each year. Boston is the perfect weekend getaway for couples, solo travelers, and families no matter what your interests. For those wanting to take a walk through the American Revolution, try the Freedom Trail. This two-and-a-half-mile trail will take you through 16 historical sites, like the Paul Revere House and the Boston Commons. If art and culture are what you crave, be sure to hit the Museum of Fine Art and the Boston Public Gardens. No trip is complete without a stop at Fenway Park, home to the infamous Boston Red Sox and some of the most dedicated fans in baseball.
Boston is a city of neighborhoods, each with its own personality. Tourists will find the downtown waterfront a central location and excellent starting point for visiting the city's top attractions. The nearby Boston Harbor Hotel and InterContinental Boston are luxurious waterfront options.
Although Nantucket is known for its beaches, there is so much more to see and do on your weekend getaway here. Thirty-six miles out to sea, this island is filled with maritime history, culture, and nature, making it the perfect weekend destination for anyone looking for an escape. The remote location and simple beauty just adds to the charm. Stop by the Whaling Museum and Atheneum, which gives an understanding of the island's past. Rent a bicycle to explore. Within easy reach is the Brandt Point Lighthouse. One of the many pristine beaches like Cisco or Jetties Beach can be accessed via the local transit. Be sure to load up on the amazing seafood at one of the town's many restaurants featuring fresh and local caught delights.
The easiest way to get to Nantucket would be to fly from Boston via Cape Air, or you can drive to Hyannis and take the ferry over. It will take a few hours either way, so the journey is best made on a long weekend. In season, this resort area caters to tourists with deep pockets. The historical Jared Coffin House and The Veranda House are both within walking distance to the harbor and many restaurants.
3 Cape Cod
Cape Cod is the premier beach destination in New England and makes a perfect weekend getaway for those looking for sun, sand, and relaxation. No less than 14 lighthouses are located on the peninsula, which is more than any other county in America. More than four million visitors a year grace the 40 miles of pristine beaches. While you are there, grab a bike and check out the 25-mile Cape Cod Rail Trail, which runs from South Dennis to Wellfleet. History buffs will enjoy the Heritage Museum and Gardens, an eclectic destination with an antique carousel, automobiles from throughout history, beautiful gardens, and folk art. Another fun stop is the famous Cape Cod Potato Chip factory in Hyannis. You can tour the facility and see how these tasty treats are made.
Chatham has many options for places to stay. The Chatham Inn at 359 Main is popular for its firepit and chocolate-covered cranberries. Many of the hotels near the west end are motel-style. Midway Motel offers free Wi-Fi and parking. Additional attractions are the nearby scenic Cape Cod Rail Trail for biking and jogs.
4 Lenox, Massachusetts
Nestled in the beautiful Berkshires, Lenox is filled with small-town charm, which lends perfectly to a relaxing, low-key vacation. Year-round activities make this a favorite for family trips, romantic getaways, or solo pursuits. It becomes magical in the autumn, when the leaves change and vibrant colors fill the mountain.
If you just want to enjoy some peace and quiet, there are plenty of opportunities to do that as well. Take a class at the world famous Kripalu Center for Yoga and Health or visit the nearby Norman Rockwell Museum, which houses the largest collection of his bygone-era artwork. A trip to the Gilded Age Museum will take you back in time. If you are feeling adventurous, head out to the Ramblewild tree-to-tree adventure park.
Summer visitors will want to make sure to look into the schedule at the Tanglewood Music Center, home of the Boston Symphony Orchestra and other famous music makers mid-June through Labor Day.
Cranwell Spa & Golf Resort offers many packages for visitors, depending on your interests. The various buildings on the property offer a fitness room and indoor pool, and the location highlights the beauty of the area. Tourists will find reliable value at the Courtyard Lenox Berkshires. Families will appreciate the free Wi-Fi, firepit, and pool.
Provincetown is an eclectic town known for its vibrant culture, a picturesque harbor, and bustling art scene. P-town, as it's affectionately called, is located on the scenic end of the Cape and can be reached by ferry from Boston. This harbor town has a year-round population of 3,000, which explodes to 60,000 in the summer months. While you are here, head to Commercial Street, which is the prime people-watching destination and a fun place to grab a bite to eat, shop, or just wander around. Make a stop at the Pilgrim Monument & Provincetown Museum, which commemorates the Pilgrims' first landing in Provincetown. Take the elevator to the top of the monument, one of the tallest all-granite structures in the US to get amazing views of Cape Cod. The seasonal ferry from Boston makes for a great day trip. If your stay in Provincetown involves an overnight, the Cape Colony Inn boasts an above-ground pool among its many amenities, and the Lands End Inn offers luxurious accommodations with beautiful views of the Atlantic and beaches.
Salem is a town rich in history and scandal. This town has a dark past and was made famous by being the site of the Salem Witch Trials. Because of this, there are many attractions in Salem that pay homage to this dark time in American history. Despite its reputation, Salem is still a great weekend destination for couples with many different interests. Book lovers will enjoy stopping by the House of Seven Gables, setting for Nathaniel Hawthorne's novel of the same name.
For those adventurous souls, when dark falls on Salem, head out for the Haunted Footsteps Ghost Tour.
One of the area's best maritime-focused museums, The Peabody Essex has excellent rotating exhibitions and a 200-year-old Chinese House reconstructed inside the museum. Families appreciate the indoor pool at the Salem Waterfront Hotel & Suites, two blocks from the water. The free parking is a plus in what can be a congested area in Salem. The beautiful and historic Hawthorne Hotel is centrally located and within walking distance to many of Salem's best places to visit.
Not everyone is looking to plan a getaway to the beach. For those who want to escape Boston, but find the mountains more their style, the Berkshires is the getaway for you. Located in the western part of Massachusetts, the Berkshires hold everything you could possibly want in a weekend getaway: quaint towns, great food, terrific hiking, and the peace and quiet of quintessential New England living.
Yoga enthusiasts, can enjoy relaxation and take a class at the world famous Kripalu Center for Yoga and Health. White water rafting or ziplining are options for the thrill seeker. Historic Deerfield is an area for history buffs and must-see museums like the Norman Rockwell Museum and Susan B. Anthony Birthplace Museum. There is a little something for everyone here. Hotel on North is a loft-style boutique hotel, while those looking for a rustic stay will appreciate the log cabins at the Lanesboro Country Inn, a dog-friendly spot to break kids into the camping vibe.
For those with a love of the arts, Northampton is one of the best small arts towns in the nation. This historic town is filled with independent artists and galleries. Smith College boasts an impressive art collection in their Museum of Art. Be sure to stop by the Botanical Gardens or just walk through the historic town and take in the sights. You can also rent a bike and take a ride down the Norwottuck Rail Trail, enjoying nature and the sights by the Connecticut River. Stay at the Fairfield Inn & Suites Springfield/Northampton, about a ten-minute walk to town. This brand from Marriott includes free breakfast, Wi-Fi, and parking. Families enjoy the indoor pool, and suites are available.
Massachusetts is filled with many eclectic towns, but none more than Rockport. This seaside community sets the stage for a fun and unique weekend getaway. Just an hours' drive from Boston, you will feel like you are a thousand miles away when you step foot into this quaint village. While you are here, check out the iconic Motif #1, a famous painted fishing shack. Walk down to Bearskin Neck, which is filled with unique shops, restaurants, and art galleries or just enjoy the magical views, which have inspired artists for centuries. Away from the hustle and bustle of Rockport proper, The Seafarer Inn offers a waterfront location across the street from a small beach. If a bed-and-breakfast is more to your liking, The Tuck Inn is very popular and has an extensive breakfast filled with delicious offerings.
For couples and families who want to experience a true New England fishing village, head to Gloucester. This quintessential New England town houses the country's oldest seaport and was a prominent shipbuilding town. Here, you will find the Fisherman's Memorial, one of the most noted and photographed statues in New England.
Gloucester is great for whale watching. These gentle giants can be seen from shore or for the more adventurous, you can head out with one of the many other charters in town. Gloucester is also home to the centuries-old Rocky Neck Art Colony, the oldest working art colony in America Head here to check out one of Rockport's many art galleries. Before you leave, you have to indulge in one of the prized local seafood restaurants to enjoy the ocean's bounty. The typically New England Beauport Hotel Gloucester is located on the waterfront in Gloucester with a rooftop pool. Plenty of restaurants in the city's bustling center reward visitors with a variety of options after a day in the sun.
Affectionately referred to as "America's Hometown," Plymouth is best known for being where the Pilgrims landed in 1620. A trip to Plymouth wouldn't be complete without a stop at Plymouth Rock where it all began. You can also check out one of Plymouth's many historic attractions, like the Plymouth Grist Mill, a working mill that has been in operation since 1636 and opens to the public on Fridays at noon. Another must-see is the W. Russell Blake Planetarium. Visitors experience astronomy with the only 4K high-resolution fulldome planetarium south of Boston. The Hilton Garden Inn Plymouth is a popular, good-value hotel with a central location and free Wi-Fi. The splurge-worthy Mirbeau Inn & Spa at The Pinehills is luxury at its best.
12 Martha's Vineyard
Martha's Vineyard is the perfect getaway to leave the hustle and bustle of Beantown behind. This island has long been a prized vacation spot for Boston's elite, and others just wanting to escape, and is a larger island alternative to Nantucket. While you are here, rent a bicycle so you can explore the island at your leisure. On the southwestern tip of the island is Aquinnah Cliffs, a popular tourist spot, where you can see the impressive clay cliffs. From the top, you can view the Gay Head Light or Elizabeth Islands. For animal lovers, head to Island Alpaca, where you can meet one of the friendly Huacaya alpacas and tour the beautiful farm. The main draw to Martha's Vineyard is the beach, so be sure to enjoy the ocean, sand, and sunshine on your trip. Martha's Vineyard is a few hours from Boston, but well worth the drive. You can also reach it via ferry or plane.
Direct flights are available from Boston and New York City. The boutique Vineyard Square Hotel and Suites in Edgartown has seaside charm and modern décor. If you're looking for a luxury splurge, the beachfront Winnetu Oceanside Resort should be on your shortlist. Nestled in the dunes, it has quite a selection of suites, cottages, and private homes making this destination a great choice for multi-generational travel.