Rent Luxury Accommodation in Massachusetts

We selected the 932 homes worth renting in this location

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Home spotlights in Massachusetts

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

Ponder & Wander

Ponder & Wander

  • 12 guests

  • 4 bedrooms

Wilmington, Windham County

Set on 22 acres of private land boasting ponds, streams and an abundance of nature – this spot in Wilmington offers a peaceful escape beyond the realms of city living. Perfect for larger groups, up to three families can stay here comfortably, with three ensuite bedrooms spread across two floors and an expansive living room on each floor - both overlooking the ponds, one with vaulted ceilings.

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Dating back to the eighteenth century, it’s safe to say that The Whaler’s Cottage is steeped in history. It has a wonderful garden with lots of room for relaxing, and the interiors are stunning.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.


We selected the top 3% holiday homes in Massachusetts Accommodation

Explore the 932 most perfect homes in our collection

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Most popular homes in Massachusetts

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable County

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

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Frequently asked questions

Take a look at our exclusive collection of luxury Accommodation in Massachusetts, United States, and find your dream home. Each and every listing on our site has passed a vigorous testing process with flying colours, which is why we can be so certain that our collection is the best of the best. Only 3% of homes will ever make it onto Plum Guide, emphasising our incredibly high standards and making your job as easy as possible. Every home comes fully furnished with a perfectly-equipped kitchen, essential bathroom toiletries, and all linen included, so you will find everything you need. Get in contact with our friendly team of experts, whose sole purpose is to find you your ideal home, and book your stay in the finest Massachusetts Accommodation for Rent.

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