Rent Luxury Accommodation in Massachusetts

We selected the 36 homes worth renting in this location

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Home spotlights in Massachusetts

Sail of the Century

Sail of the Century

  • 16 guests

  • 6 bedrooms

Stonington, Connecticut

Sitting on the edge of Mason's Island, this waterfront location doesn't just bring peaceful views of Fisher Island Sound – there's also a private beach plus a dock so you can fill your stay with swimming and watersports. If relaxing is more your bag, the large terrace has plenty of seating, plus an impressive outdoor kitchen for when dinnertime rolls around again.

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.

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Originally built in the 1800s as a fisherman’s shanty, this traditional cedar-shingled building has since been restored into a peaceful waterside sanctuary – it's the perfect setting to relax, reflect and listen to the soothing sound of the sea. Inside, the owners have honoured the integrity of the space whilst integrating a range of vintage and handcrafted furnishings – each with its own story and tale from travels near and far.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.


We selected the top 3% holiday homes in Massachusetts Accommodation

Explore the 36 most perfect homes in our collection

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Most popular homes in Massachusetts

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable 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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