Family Vacation In Massachusetts

Sometimes planning a family vacation can be a hassle, especially if you have a busy life. Many people will plan to travel in the summer since it is the slow season for the holidays and there are usually less people traveling during the summer months. If you are planning a family vacation in Massachusetts, here are some places that you should visit.

Planning the family vacation can be stressful. You want to plan a great vacation that everyone will enjoy but you need a place to stay, something to do everyday, and entertainment for all of the kids. You need a place that is affordable and fun. With Massachusetts so close by you will get a great family vacation but you also guarantee affordability as well as something fun to do every day for each person!

Family Vacation In Massachusetts

It is an irrefutable fact that family vacations are beneficial. Yes, one of the reasons for this is due to the fact that it requires you to spend time with your family which can be beneficial in itself . Aside from spending time with family however, trying new things is another benefit of going on a vacation. Even when you go on a vacation within your own state or region, there will still be something new for your to see and experience. One of the most splendid parts of the United States is undoubtedly its magnificent coast-lines. In December, it isn’t so bad to escape the cold and go bask in the sun. Although choosing a resort with your family may be a bit difficult if you aren’t quite sure about what you want, here are a few tips that might help.


We can’t talk about weekend getaways in Massachusetts without mentioning Boston. Boston is not only the most populated city in the state, but it’s the state’s capital. This capital city is rich in history and has more than enough to keep you and your family busy for the entire weekend. 

Boston is the perfect place to bring your family because while it’s packed to the brim with history, it also has its fair share of new things to see. One of the best things to do on your weekend getaway in Boston is to walk the Freedom Trail. 

This historical, two-mile trail will take you to 16 historical spots, including the Boston Commons and the Paul Revere House. The Boston Commons is a beautiful place to sit back and relax with the family and enjoy a nice picnic. 

A trip to Boston doesn’t need to only be focused on history, the aquarium is stunning, and kids love looking at all the marine life. If your family are museum buffs, there’s the Boston Tea Party Museum, the Contemporary Art Museum, and more. 

Whether you and your family are baseball fans or not, you can’t miss out on seeing Fenway Park. The stadium itself is fantastic, but the area that it’s located in offers a culture all its own that’s worth hanging out at for a bit.

There are hundreds of places to stay on your trip to Boston, but if you’re looking for a place that’s right in the heart of the city, the Boston Marriott Long Wharf is a great option. There are plenty of vacation rentals located throughout, too, if you’re not interested in a hotel. 

Cape Cod

If you’re looking for a coastal getaway in Massachusetts, Cape Cod needs to be on your list. Your perfect family beach getaway is calling your name. Cape Cod is known as the premier beach destination in New England. 

There are over 130 beaches for you and your family to soak up the sun on. For the more adventurous people in your family, you can find some great surfing spots on the peninsula too. One of the most popular beaches in Cape Cod is Craigville Beach. It’s on the south shore and is a great place to start and end your beach getaway. 

Something people of all ages love doing on their vacation here is renting bikes. There’s a beautiful 25-mile walking and biking trail that shows you some of the best views you’ll find in Massachusetts. 

Did you know that Cape Cod has the most lighthouses in one county in the entire United States? Even if you’re not a huge lighthouse fanatic, experiencing even one of these beautiful structures is a must-do while in Cape Cod.

Let’s face it. Everyone loves potato chips. A fun activity to do while on vacation is to visit the Cape Cod Potato Chip Factory. You and the whole family will love seeing how they make these chips, the history surrounding the company, and munching on samples. 

Golfing is popular in Cape Cod; there are several golf courses for you and the family to schedule a tee time at. Some even offer golf lessons if you’ve never played before and want to try something new. 


There are several small towns on Cape Cod, but Provincetown deserves mention on this list. Provincetown, or P-town, is at the very tip of the Cape Cod peninsula, past the Cape Cod National Seashore. It’s also the landing site of the Mayflower in 1620, which is exciting to share with your family.

You and your family can dive through Cape Cod until you reach Provincetown, or you can travel from Boston by ferry. If you or anyone else in your family haven’t been on a ferry before, it’s a fun way to get to your weekend destination. 

P-town is generally a tiny coastal town most of the year, but during the summer months, its population more than quadruples. When in P-town, spending time at their beaches, hiking the dune trails, and exploring the various nature preserves is common with families. 

See also 12 of the Best Luxury Hotels in Boston for Families

Commercial Street needs to be on your list because not only is it the center point of the town, it has some of the best restaurants and places to people-watch in the entire city. You won’t want to miss seeing the pilgrims landing park and the Pilgrim Monument, and Provincetown Museum. 

Even for a small town, there are several fantastic places to stay. Some of our favorite options include the Harbor Hotel, the Seaglass Inn and Spa, and for those interested in a more rustic experience, the Dunes Edge Campground. 


Salem is another wonderful place for a weekend getaway with the family. You’ll find Salem on the north coast of Massachusetts, and it’s been made famous for its dark past. You may have heard of Salem because it was made famous by the 1692 witch trials. 

One of the biggest attractions to visiting Salem is experiencing all the history surrounding the alleged witchcraft and trials that took place centuries ago. You can see the now historical sites including, The Salem Witch Museum and The Witch House. If you and your family are up for it, taking a ghost tour through the city is a mysterious and thrilling way to experience Salem. 

Even though Salem is known for alleged witches, there’s much more to do in the city if you’re looking for other things to fill your weekend. For movie buffs, you can travel around the town looking at all the filming locations of the famous 1993 film, Hocus Pocus. 

The House of Seven Gables is a must-see when in Salem, whether you’ve read the novel or not. For art lovers, the Peabody Essex Museum is filled with artwork and artifacts that people of all ages will be fascinated by. 

The Salem Waterfront Hotel and Suites is a great lodging option. You’ll find it on the water, near the Peabody Essex Museum. If you’re looking for something closer to the city center, the Hawthorne Hotel is popular for families. 


It’s safe to say that Massachusetts is filled with tons of historical significance. While Provincetown is where the Mayflower first landed, Plymouth is considered the first pilgrim settlement in the United States. 

You’ll find Plymouth south of Boston, along Cape Cod and Plymouth Bay. Many people refer to this small coastal town as America’s Hometown since it’s the first pilgrim settlement. You and your family will love exploring the city and taking in the rich history. 

Some of the best historic sites and museums to visit are the Monument to the Forefathers, Pilgrim Hall Museum, and the Plimoth Patuxet Museums. At the Plimoth Patuxet Museums, you and your family can see real-life replicas of the houses and other establishments the pilgrims lived in back in the 1600s. There’s also a reconstructed Mayflower to view. 

If you’re looking for additional things to do in Plymouth besides taking in the history, there are several beaches for you and your family to spend the day at when the weather is nice. Two of the most popular beaches include Plymouth Beach and Pricilla Beach. 

You won’t want to miss out on walking around the Lobster Pound. This seafood market celebrates everything there is to love about seafood, which New England is known for. 

If you need recommendations on where to stay while in Plymouth, The Pilgrim Sands Hotel on Long Beach is perfect because it’s centrally located and right next to the longest beach in the town. 

Great Barrington

For those looking for a mountain escape, heading to the Berkshires, specifically Great Barrington, might be the best getaway for you. This small mountain town is perfect for the outdoorsy family. 

Whether you visit Great Barrington during the summer, winter, or other seasons, there’s plenty of things to do. Most people flock to this area of Berkshire county to experience the ample hiking, walking, and biking trails. 

Some of the most popular trails and nature areas are Foundation Pond State Park, Beartown State Forest, and Monument Mountain Reserve. During the winter, you’ll find that one of the best places to visit in Great Barrington is Butternut Ski and Tubing Resort. You can stay at this resort during your trip or take some time to ski and tube on their slopes.

In the center of this small town, they have their own Riverwalk. The Riverwalk runs through town along the Housatonic River. It’s a short nature trail that people of all ages can enjoy while you’re exploring the city. 

For those who don’t want to stay at the ski resort or aren’t visiting during the winter, The Wainwright Inn Bed & Breakfast is a great choice for families. 

Martha’s Vineyard

Martha’s Vineyard is an island colony located south of Cape Cod. It’s a familiar spot for people living in Boston on the eastern coast of Massachusetts to spend their summers or a weekend away. 

See also 9 of the Best Water Parks in Massachusetts

The Vineyard is filled with traditional cottages, sandy beaches, and farmland. If you’re looking for the perfect summer, weekend getaway, Martha’s Vineyard is a great place to be with your family. There are 19 beautiful beaches on the island to choose from where you can soak up the New England summer sun. 

The south side of the island is the perfect spot if you or someone in your family loves to surf. If you’re not a surfer, but someone else in your party is, you can kick back with a good book while they catch some waves. 

There are several cliffs to look out over, and the views are spectacular. The Aquinnah Cliffs are some of the most popular and most accessible to get to with children. Since Martha’s Vineyard is a New England island, you won’t want to miss out on the freshly caught seafood. 

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