Massachusetts Family Friendly Hotel Alternatives

We selected the 36 homes worth renting in this location

Home spotlights in Massachusetts

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.

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.

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.


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

Explore the 36 most perfect homes in our collection

View on map

Most popular homes in Massachusetts

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable County

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Pondering Soul

Pondering Soul

  • 14 guests

  • 7 bedrooms

Copake, New York

Trees & Caramel Pine

Trees & Caramel Pine

  • 8 guests

  • 3 bedrooms

Lenox, Berkshire County

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London 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

View all

Check upcoming rates & availability for Massachusetts Family Friendly Hotel Alternatives


Frequently asked questions

Explore our family friendly hotel alternatives in Massachusetts, United States. We’ve cherry-picked a collection of spacious homes in safe, residential neighbourhoods popular with local parents. Find a fully furnished home with fun kids' bedrooms, well-equipped kitchens, multiple bathrooms and often outdoor space too. Our friendly team of Plum Experts are on-hand 24/7 to help you book your dream family friendly hotel alternative in Massachusetts, United States.

Search Our Collection