Book Luxury Short Stay Rentals in Massachusetts

We selected the 930 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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Infants

Under 1

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Pets

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Home spotlights in Massachusetts

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

The Road Not Taken

The Road Not Taken

  • 12 guests

  • 5 bedrooms

Windham, Greene County

Surrounded by twelve acres of towering pine trees, days at this Catskills cabin are best spent in the great outdoors. Start the morning with a coffee on the deck, followed by a stroll through the private trail in the forest.

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.

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.


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

Explore the 930 most perfect homes in our collection

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Most popular homes in Massachusetts

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Dahlia Darling

Dahlia Darling

  • 10 guests

  • 5 bedrooms

Bethel, New York

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

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

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

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Check upcoming rates & availability for Massachusetts Short Stay Rentals


Frequently asked questions

Browse our curated collection of Short Stay Rentals in Massachusetts, United States. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Massachusetts luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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