Book Family Friendly Rentals in Massachusetts

We selected the 36 homes worth renting in this location

Home spotlights in Massachusetts

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable County

A stay in this charming home is a ticket to private beaches and waterfront access. Enjoy access to an exclusive member’s club here in North Chatham.

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

When you want to get away from the hustle and bustle, this New Lebanon home is the perfect choice. You’ll not only leave the hectic city behind – stepping through the doors feels a little like stepping back in time.

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. Located within a former Shaker settlement, there’s an abundance of charm and character here.


We selected the top 3% holiday homes in Massachusetts Family Friendly Rentals

Explore the 36 most perfect homes in our collection

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Most popular homes in Massachusetts

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Sail of the Century

Sail of the Century

  • 16 guests

  • 6 bedrooms

Stonington, Connecticut

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Upstate Serenity

Upstate Serenity

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Mulberry Hill

Mulberry Hill

  • 10 guests

  • 5 bedrooms

Nantucket, Nantucket County

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Massachusetts, United States. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Massachusetts Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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