Places to Stay in the Berkshires for Families: the Best AirBnBs (September 2020)

Family trips to the Berkshires are a quintessential part of life in Massachusetts. The area offers a beautiful backdrop for a family vacation. The area is known for its hikes, festivals, and farm to table restaurants. For families who want to make the most of the area, a rental property is a great option. Many houses offer relaxing outdoor spaces with fire pits, hammocks, and some even have pools.


Lenox is a favorite destination for visitors to the Berkshires. It's a small town set against the backdrop of the beautiful southern part of the Berkshires. It has a lovely downtown area that's perfect for walking. The historic New England architecture gives this hamlet a sense of character. There are a number of great local restaurants, as well as health spas and art venues. The town is also famous for its Tanglewood Music Festival, which features the Boston Symphony Orchestra.

Kids will love the hiking trails in the area. There are many trails that feature rolling hills and aren't too strenuous for little legs. Horse lovers will enjoy a trail ride, which is the perfect way to experience the Berkshires.

This town has a number of excellent vacation rentals for families. Below are some of our favorites that are in and around Lenox.

This property is all about the outdoor space. There's a private pool, a barbecue, and a firepit. It's the perfect place for a family to gather and enjoy some quality time together.

This beautiful property has large windows and plenty of natural light. It's spotless and well furnished. It's also less than a mile's walk to the downtown area and also close to Canyon Ranch.

This quaint cottage is perfect for a small family who wants to experience everything that the Berkshires has to offer. It's close to downtown and everything that Lenox has to offer. The kids will love that it's just down the street from a playground.


Stockbridge is another charming town in a central part of the Berkshires. The downtown is a bit smaller than Lenox and there are just a handful of restaurants to choose from, but there are nice trails along the Housatonic River. This town is known for its cultural sights. Make sure you check out the Berkshire Theater Group, which is popular for its plays and musicals. Kids and adults will also enjoy a visit to the Norman Rockwell Museum, where you can see a number of famous works. For food, a trip to Stockbridge isn't complete without a meal at the Lion's Den. They offer classic New England dishes that kids and adults will love.

There is also no shortage of outdoor activities near Stockbridge. Hiking and skiing are both popular in the area.

There are a number of large houses available for rent near Stockbridge. These properties are often on vast acreage and have a large amount of space for families to gather. Below are a couple of our favorites.

This large house has enough space for several families to gather and still enjoy some privacy. It's close enough to downtown to be convenient, but still removed enough to be quiet. The outdoor space is excellent. There's a fire pit and a couple of hammocks. The layout of the house is perfect for social gatherings, and guests rave about the fun and relaxing retreat this property offers.

This property is another excellent option for multiple families or a larger family reunion. Each bedroom has its own bathroom, which is convenient for groups of all sizes. The backyard is a fun place for kids to play and the location is convenient.

This cozy cabin is perfect for a family that wants to enjoy some time together. It's conveniently located near both Stockbridge and Lenox.


Pittsfield is the largest city in the Berkshires, but it still has plenty of charm and character. There is a lot for the entire family to enjoy. Pittsfield is known as the "city of festivals" and it really comes to life during the summer months when there always seems to be something going on. There's a city baseball team, a lot of parks, and plenty of activities for the family to enjoy. Kids will enjoy a visit to the Berkshire Museum, which has science exhibits, an aquarium, and even a large playroom. For the young and young at heart, a trip to Pittsfield isn't complete without a ride on the Berkshires Carousel (just $2).

One of the more popular destinations is the Herman Melville House, also called Arrowhead. Today it's a museum where you can learn about how this famous author of Moby Dick lived and worked. Theater lovers will also enjoy a visit to the Colonial Theater, which is part of the Berkshire Theater Group.

Because Pittsfield is larger than the other towns, many of the properties are a bit smaller. They're also more affordable than what you find in other towns in the Berkshires, so if you're looking for value at budget prices, then this is the place to stay.

This apartment can fit a small family. It's clean and comfortable and a good value for anyone who wants to escape to the Berkshires.

Great Barrington

Great Barrington has one of the larger downtowns in the Berkshires and there are plenty of restaurants, shops and activities to choose from. Kids will also love a visit to the Mahaiwe Theater. For a kid friendly meal, head to Baba Louie's for pizza and then shop in some of the kid centered stores around town. To explore the area's art galleries, head to Housatoni, which is also where you'll find the town's old paper mill.

There are also a number of great kid-friendly hikes in the area. A favorite for families is Monument Mountain, which isn't far and includes just a slight incline. Also near town are a number of natural swimming areas and skiing.

There are a number of nice vacation rentals for families in the area.

This Victorian house is conveniently located whether you want to ski, visit the lake, or head into town. It has a lovely shaded backyard that's great for kids and a front porch that's perfect for relaxing with a good book.

This property is all about the personal touches, from the gift basket and tour when you arrive to the hammock and outdoor space where you can relax. The pantry is well stocked, and the location is great for a family.


Williamstown is a charming college town in the northern part of the Berkshires. It's a great spot for families who enjoy hiking and museums. The town is home to Williams College, which has some great galleries and museums. In particular, visitors enjoy the Williams College Museum of Art and the Clark Museum, which is just outside of the downtown area.

There are a number of great hiking areas near town as well. Just outside of town is Mt. Greylock, which is the highest peak in Massachusetts. Also nearby are the Taconic Trail State Park, Field Farm, and Bullock Forest.

Williamstown has a wide variety of rental properties to choose from. There are smaller, more affordable condos and apartments, but families usually enjoy the larger houses, which offer more room and outdoor space where the entire family can play.

This historic home has no shortage of character. It's perfect for a large family, or even several families. There are games and books that kids will enjoy, a fully stocked kitchen, and a location that makes the perfect escape for your family.

This charming cottage is a great option for a family of four or six. It's walking distance to the college, restaurants, and shopping. It's a well maintained house with a fully stocked kitchen and a comfortable setting.

This house is all about the setting. It offers impressive views of the Berkshires and is off a beautiful country road.


Lee has a historic downtown and a laid back down-to-earth vibe that visitors love. The downtown has a number of historic buildings including the Congregational Church, the Lee Library, and the Civil War Memorial Hall. There are also a number of Victorian homes in the area.

Outside of the downtown area, visitors enjoy shopping at the nearby outlet mall. There are also a number of restaurants in the area. Kids and adults alike will enjoy spending time at Laurel Lake which offers a quintessential mountain experience.

This property really is the perfect setting for a family vacation in the Berkshires. It's large with plenty of bedrooms and bathrooms for everyone. There is a great porch and backyard with a fire pit. The kitchen is open and great for socializing and the house is beautifully maintained and well stocked.

This house is beautifully renovated and offers lots of natural light. The neighborhood offers a peaceful setting near many of the area's best hikes and lakes. There is also a pool table, two living rooms, and a well stocked kitchen.

This property is all about the location. It sits by a beautiful, secluded lake, and in the area you'll find a number of great hikes that the whole family can enjoy. This makes the perfect retreat for a family that's looking for a peaceful setting.

North Adams

North Adams is home to a number of historic churches, giving it a charming skyline. The area is filled with forests, parks, and beautiful landscapes. Visitors enjoy going to the Massachusetts Museum of Contemporary Art, which is the largest contemporary art museum in the country. For kids who enjoy trains, a visit to the Western Gateway Heritage State Park is fun. It's located in the restored freight yard district and has a number of railroad exhibits. Also nearby is Natural Bridge State Park as well as a number of great hiking trails.

This apartment is located in a historic building just outside of the downtown area. It's within walking distance to the Massachusetts Museum of Contemporary Art and is a nice space for a family.

Happy Travels!
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