Book a stay in one of the best homes in Massachusetts

We selected the 39 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.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

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.

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

Explore the 39 most perfect homes in our collection

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Most popular homes in Massachusetts

The Lakehouse

The Lakehouse

  • 10 guests

  • 4 bedrooms

Morris, Litchfield

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Upstate Serenity

Upstate Serenity

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

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