Book a stay in one of the best homes in Massachusetts

We selected the 41 homes worth renting in this location

Home spotlights in Massachusetts

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

There are some homes that simply capture your heart from the moment you arrive. And we won’t be surprised if it’s love at first sight when you see this charming Colonial saltbox house.

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.

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.


We selected the top 3% holiday homes in Massachusetts

Explore the 41 most perfect homes in our collection

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Most popular homes in Massachusetts

Sail of the Century

Sail of the Century

  • 16 guests

  • 6 bedrooms

Stonington, Connecticut

The Lakehouse

The Lakehouse

  • 10 guests

  • 4 bedrooms

Morris, Litchfield

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Trees & Caramel Pine

Trees & Caramel Pine

  • 8 guests

  • 3 bedrooms

Lenox, Berkshire County

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

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