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Luxury Long Stay Rentals in Massachusetts

We selected the 932 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Massachusetts

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.

Victorian Gingerbread

Victorian Gingerbread

  • 6 guests

  • 4 bedrooms

Oak Bluffs, Dukes County

Built in 1871, this picture-perfect cottage has been beautifully renovated while retaining the most important elements of its original design. We're talking wood panelling, timber beams, and arched windows and doors.

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Clued-up New Yorkers have slowly been turning their attention away from the Hamptons to this corner of countryside in Litchfield County. One step into this home, and we can see why they're making the swap.

We selected the top 3% holiday homes in Massachusetts Long Stay Rentals

Explore the 932 most perfect homes in our collection

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Most popular homes in Massachusetts

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

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

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

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Check upcoming rates & availability for Massachusetts Long Stay Rentals

Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Massachusetts, United States. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Massachusetts, United States collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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