Massachusetts may have travel restrictions in place, including self-quarantine, due to COVID-19.

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Book Massachusetts Vacations

Save up to $374^ on your trip when booking flight + hotel together

Trip deals to Massachusetts for 2021

The Godfrey Hotel Boston
Courtyard by Marriott Boston-Cambridge
Moxy Boston Downtown
The Inn at Thorn Hill & Spa
The Liberty, a Marriott Luxury Collection Hotel, Boston

Top Massachusetts vacation deals

Courtyard by Marriott Boston-Cambridge
Moxy Boston Downtown
The Godfrey Hotel Boston
The Liberty, a Marriott Luxury Collection Hotel, Boston
Sheraton Boston, a Marriott Hotel

Best Massachusetts Package Vacations

Packed full of things to see and do, Massachusetts vacations offer non-stop adventures for solo travelers, couples and families. With plenty of summer vacation destinations to choose from including Cape Cod and the indulgent luxury of Martha’s Vineyard, to historic Boston and spooky Salem, vacations in Massachusetts are never dull. Keep reading for our travel guide to vacations in the Bay State and find your perfect New England vacation spot.

Why Vacation in Massachusetts?

Easy to get to by air and road, Massachusetts offers so many things to do for visitors. For a family vacation, there’s no better place than Cape Cod where water sports, relaxing walks, and incredible food are all part of the trip. Historic Boston has a unique personality and shows off all its best places to tourists throughout the year. Surround yourself with academia in the college town of Cambridge or be awed by Fenway Park.

Must-See Massachusetts Attractions

History buffs on the trail of the American Revolution will love stopping by Plymouth Rock to see where the story of the United States really began. Located south of Boston and on the way to Cape Cod, this historic rock is a Massachusetts landmark and one of our most important locations. After you’ve learnt about those first settlers, you can take a walk along Plymouth Long Beach and enjoy the view.

Salem in October is a unique experience, but visit this town at any time of the year and you’ll love the tranquility and beauty of this corner of New England. During your visit to the home of the Salem Witch Trials, take a spooky tour of Salem’s historic buildings and hear all about the strange happenings that went on here in the 17th century. Salem is a classic Massachusetts vacation destination during Halloween, but don’t cross it off your list during the rest of the year, especially in spring!

Top Vacation Destinations in Massachusetts

1. Cape Cod - If you’re on the hunt for summer vacation ideas then Cape Cod will tick all of your boxes. This beach community is perfect for a family vacation, with lots of water activities on offer as well as walking trails marked by the coast’s iconic lighthouses. Snack on fresh seafood in one of the many beachside shacks and make Cape Cod your new summer home.

2. Boston – This unique city is a great place for a busy vacation. Wander the paths of Boston Common, follow the Freedom Trail, and check out the cultural offerings like the Boston Symphony Orchestra. Don’t forget to try a lobster roll and round it off with a Boston cream pie.

3. Martha's Vineyard - Escape the busy mainland with a summer vacation on Martha’s Vineyard. Booking a Massachusetts package vacation on this island will make any stress disappear and the whole family will love the beach strolls and fabulous views.

4. Nantucket - With pretty harbors and the famous whale museum, Nantucket Island is a truly blissful destination. Book one of the vacation rentals on offer that sit right on the shoreline and wake up to the sounds of the sea.

5. The Berkshires - Out in western Massachusetts, this is the best place in the state for hiking, mountains, and rolling hills. In summer you can catch the Boston Symphony Orchestra playing in Tanglewood, and in fall you’ll see the most exquisite colors in the trees.

Best Time To Visit Massachusetts

Vacations in Massachusetts can be taken any time of year, thanks to the state’s distinct seasons. A summer vacation on the east coast will see temperatures up to 78°F, while spring and fall are the most beautiful seasons for hiking out in the Berkshires. Winter in Massachusetts means cozy Boston nights in a warm and friendly bar, and great skiing out in western Massachusetts.

Getting Around Massachusetts

Fly into Boston Logan (BOS), TF Green (PVD) for the east coast or Bradley International (BDL) in Connecticut for western destinations. Massachusetts is well connected by road too, with major highways crisscrossing the state. Boston’s public transport system is excellent.

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