Book Luxury Monthly Rentals in Massachusetts

We selected the 916 homes worth renting in this location

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Home spotlights in Massachusetts

The Berkshires Splendour

The Berkshires Splendour

  • 14 guests

  • 6 bedrooms

New Marlborough, Berkshire County

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.

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.


We selected the top 3% holiday homes in Massachusetts Monthly Rentals

Explore the 916 most perfect homes in our collection

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Most popular homes in Massachusetts

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Mulberry Hill

Mulberry Hill

  • 10 guests

  • 5 bedrooms

Nantucket County, Massachusetts

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Sweet Cicely

Sweet Cicely

  • 6 guests

  • 3 bedrooms

Ulster County, Woodstock

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Massachusetts, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Massachusetts Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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