The Best Homes in Massachusetts

Award-winning homes from £98

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.

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.

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.


We selected the top 3% holiday homes in Massachusetts Best Homes

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

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

The Lakehouse

The Lakehouse

  • 10 guests

  • 4 bedrooms

Morris, Litchfield

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Beauty & Peace

Beauty & Peace

  • 8 guests

  • 5 bedrooms

Cornwall, Litchfield

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Mulberry Hill

Mulberry Hill

  • 10 guests

  • 5 bedrooms

Nantucket, Nantucket County

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Frequently asked questions

Searching for your dream home in Massachusetts, United States? You've come to the right place: we’re the official selection of the world’s best homes. Our collection of homes in Massachusetts, United States come fully furnished with well-equipped kitchens, toiletries in bathrooms & all linen included. We obsessively check each home for you, so you can book a short or extended stay with peace of mind.

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