Massachusetts Luxury Houses

Award-winning homes from £98

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Home spotlights in Massachusetts

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

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.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.


We selected the top 3% holiday homes in Massachusetts Houses

Explore the 234 most perfect homes in our collection

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Most popular homes in Massachusetts

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Mulberry Hill

Mulberry Hill

  • 10 guests

  • 5 bedrooms

Nantucket County, Massachusetts

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Victorian Gingerbread

Victorian Gingerbread

  • 6 guests

  • 4 bedrooms

Oak Bluffs, Dukes County

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Frequently asked questions

All Plum Guide houses in Massachusetts, United States have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each house in Massachusetts, United States before approving it, so you can book with peace of mind.

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