Best Massachusetts Vacations

Welcome to our Massachusetts vacations guide. Depending on your interests, you could fill your time in Massachusetts with sports, history, exciting activities, or a little bit of everything. Whether you're simply flying in for a weekend getaway, or you're bringing the entire family for a week or two, you'll never have a boring moment in The Bay State. To help you plan your trip, here are some of the best things to do in Massachusetts.

See it All from the Skywalk Observatory and Exhibit

Massachusetts vacations aren't complete without a trip to Boston. To see all of the town in a single glance, take a ride to the top of the Prudential Building . From 50 floors up, the views are breathtaking. You'll also have a chance to learn a little bit about this city's history through a self-guided tour, a movie, and an exhibit featuring the earliest immigrants that moved to Boston.

Get a Taste of Americana at the Norman Rockwell Museum

Located in The Berkshires, this monument to Norman Rockwell features some of his best paintings. As you admire his masterpieces, you'll feel like you've stepped back in time. Unlike many types of art, even the kids will be interested in these little self-contained stories.

Experience Unique Shopping at Faneuil Hall

As part of your things to do in Massachusetts itinerary, Faneuil Hall (in Boston) may be the most unique item. This urban marketplace offers more than an eclectic mix of funky boutiques

and tasty restaurants; it's filled with street performers, wandering musicians, and even clowns on tricycles. Also known as the Quincy Market , this area is comprised of four historic buildings included on the Freedom Trail .

Play in the Dirt at Coonamessett Farm

If you're enjoying a beach vacation on Cape Cod, don't miss out on Coonamessett Farm . Most visitors stay in vacation rental homes on Cape Cod, allowing the family to enjoy home-cooked meals prepared in their fully-equipped kitchen. A visit to The Farm gives you the chance to pick your own fresh berries, herbs, and veggies to enjoy during family dinners. You can even pick some fresh flowers to add another layer of fragrance to the invigorating salt air that gives all the sea-side homes a special quality. To entertain the kids, the Farm also has a petting zoo filled with sheep, chickens, goats, and alpacas.

Get Your Fill of Nature at the Cape Poge Wildlife Refuge

Just getting to Cape Poge is an adventure. From Edgartown, visitors take a ferry to Chappaquiddick Island before crossing the deserted beach in Safari-style trucks to reach the lighthouse. Along the way, you might see any number of endangered birds and other native animals. In this secluded area, the kids are definitely allowed to be kids! Let them race up the lighthouse stairs to get a bird's eye view of the entire refuge area. Who knew Massachusetts vacations could be so wild?

See a Professional Team in Action

Time your visit just right, and your things to do in Massachusetts list could include seeing one of these professional teams make the state and their fans proud:
  • Boston Bruins
  • Boston Celtics
  • Boston Red Sox
  • New England Patriots
  • New England Revolution

You'll Never Forget a Boston Duck Tour

No, you won't be looking for ducks with that famous Boston accent. Instead, you'll see all that this famous city has to offer from a WWII Duck Boat, an amphibious vehicle. As you go from street to waterway without ever leaving your seat, you'll be entertained by a humorous guide who mixes in more than a few bad, but funny, jokes along with actual historical facts.

As you can see, Massachusetts vacations are full of fun, excitement, and history. What are you planning to do during your trip?

Massachusetts Vacation Rentals

Enjoy Fabulous Waterviews & Beach Access from this Historic House

Situated in the East End on Mayflower Heights this quaint quiet area captures the imagination of an era gone by. Enjoy your vacation in this spotless, well-maintained, eclectically designed private residence. This hilltop escape provides panorami...

Family Reunion Home w/ Heated Salt Water Swimming Pool. Central A/C. Free Wi Fi

Brand new home with new furnishings and central air conditioning. Child safe, private, gated, professionally landscaped yard, with Paverstone Patio and heated in ground saltwater swimming pool, with safety cover. Family room with Pioneer Flatscre...

Waterfront Delft Haven Historic West End Cottage with Parking. Finest Location.

Directly on the beach! Situated on Commercial Street in the historic West End of Provincetown, a 1930's shingled cottage right on the shore. The tastefully furnished cottage has been completely renovated with lofty vaulted ceilings, walls of windo...

Relax and Play! Restful Lewis Bay Home, Walk to Beach and Attractions!

Your beach home awaits! Stick your toes into the sand, hear the seagulls, sail away or just listen to your family’s laughter as you unwind on your getaway. Lewis Bay Retreat welcomes you as guests and leaves you hopelessly in love with Cape Cod. ...

Beautiful Apartment - 5 miles North of Boston, Walk to Public Transportation

PLEASE NOTE: THIS AD HAS NEVER BEEN POSTED ON CRAIGSLIST. Celebrating our 6th year hosting guests from all over the world! With over 1,300 square feet of living space this fully-furnished apartment is located on the 2nd Floor a charming brick t...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email