Favorite destinations for Massachusetts vacation rentals

One of the picture-perfect states in New England, Massachusetts offers an unforgettable getaway in the nation’s north-east. It’s a much-loved destination where sandy beaches, colonial history, and seafood dining are all part of the package, but each town still manages to deliver a unique experience – not to mention a smart line-up of vacation home rentals to call home for a while. Dive in to discover where you’ll find some of the best.

Baseball, boats, and the Freedom Trail in Boston

It only seems right to start a round-up of the best places to find Massachusetts vacation rentals with Boston. The state’s capital is one of the nation’s oldest cities and it’s one that’s packed with must-sees and must-dos. In the summer months, visitors can join an excitable home crowd to cheer on the Red Sox at beloved Fenway Park or rent a paddle boat to glide across the lake in the Boston Public Garden. Stay in a Boston vacation rental in winter, on the other hand, and you’ll find it a lovely time to wrap up warm and explore a snow-sprinkled Boston Freedom Trail.

Cultural appeal and natural delights in the Berkshires

You might say that the Berkshires is a place of many talents. It’s certainly a region of New England that’s well known for its cultural attractions – though its setting amidst a lush green valley surrounded by mountains affords it plenty of natural appeal too. Choosing vacation rentals in the Berkshires might mean scoring a home base in Lenox, a small town blessed with countless delights of its own. There's Tanglewood Music Center for starters, this iconic venue the summer home of the famed Boston Symphony Orchestra, as well as gorgeous outdoor spaces like Pleasant Valley Wildlife Sanctuary and the winding Housatonic water walkway.

Windswept beaches and whitewashed lighthouses in Cape Cod

A land of quaint coastal villages, white-washed lighthouses, and ocean beaches lined with seafood shacks, Cape Cod has all the ingredients for an unforgettable summer vacation. Rentals pepper the peninsula, though those in Eastham and Orleans offer the easiest access to the windswept beaches of the Cape Cod National Seashore. Then comes Falmouth, vacation rentals here on the doorstep of the 19th-century Highfield Hall and Gardens and the landmark Nobska Lighthouse – and the town itself within a 35-minute mini-cruise of Martha’s Vineyard.

Carousels and cliff-top walks on Martha’s Vineyard

Speaking of Martha’s Vineyard, vacation rentals on Massachusetts’ pretty resort island prove an ever-popular pick for summer getaways. Those visitors arriving in Oak Bluffs on a ferry from Falmouth often stay put, the ocean-front rentals here close to some of the island’s best-loved attractions – including the wonderfully nostalgic Flying Horses Carousel and the Oak Bluffs Campground’s brightly painted Gingerbread Cottages. Those who do venture further afield can squeeze in a little culture at the Martha’s Vineyard Museum in Edgartown and enjoy breezy walks along the Aquinnah Cliffs.

Witch trials and wonders in Salem

Forever known for its 17th-century witch trials, Salem showcases its legendary history at attractions like Howard Street Cemetery and the Witch House Museum. There’s more to this seaside town than spooky goings on, though – not least a fascinating maritime heritage that’s perhaps best showcased at the Peabody Essex Museum. Salem lighthouse tours are available for much of the year but are especially enjoyed by those travelers plumping for summertime stays in Salem vacation rentals.

Four flavors of New England in Cape Ann

Cape Cod may get a lot of attention where vacation home and cottage rentals in Massachusetts are concerned, but it’s by no means the state’s only spot to serve up an idyllic backdrop for an escape from home. Perched on the shores of the sprawling Massachusetts Bay, Cape Ann is made up of four towns – Manchester-by-the-Sea, Rockport, Essex, and Gloucester, rentals in any one of them offering an authentic New England experience and easy access to almost 60 square miles of beaches, boats, and blissful times.