Book Luxury Vacation Rentals with a Private Chef in Massachusetts

We selected the 918 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Home spotlights in Massachusetts

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.

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.

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.

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.


We selected the top 3% holiday homes in Massachusetts Vacation Rentals with a Private Chef

Explore the 918 most perfect homes in our collection

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Most popular homes in Massachusetts

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

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Frequently asked questions

Explore our unbeatable collection of luxury Vacation Rentals with a Personal Chef in Massachusetts, United States. Each and every home in our range comes fully furnished with excellently-equipped kitchens, essential bathroom toiletries, and all necessary linens included. Tested aspects of any home range from Wifi speed and shower pressure to a space's feel and design, so there really is nothing left to chance on our mission to discover the greatest properties on offer. Enjoy a stay in one of the Holiday Rentals in Massachusetts with a Private Chef today, and remember your trip for all the right reasons. And don't hesitate to contact our team of experts if you require any assistance, as it is their pleasure to help make the process easy.

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