Book Luxury Airbnb Alternatives in Massachusetts

We selected the 916 homes worth renting in this location

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Home spotlights in Massachusetts

Ponder & Wander

Ponder & Wander

  • 12 guests

  • 4 bedrooms

Wilmington, Windham County

Set on 22 acres of private land boasting ponds, streams and an abundance of nature – this spot in Wilmington offers a peaceful escape beyond the realms of city living. Perfect for larger groups, up to three families can stay here comfortably, with three ensuite bedrooms spread across two floors and an expansive living room on each floor - both overlooking the ponds, one with vaulted ceilings.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 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, Nora Ephron and John Steinbeck.

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse.

A Fine Catch

A Fine Catch

  • 9 guests

  • 5 bedrooms

Chatham, Barnstable County

A stay in this charming home is a ticket to private beaches and waterfront access. Enjoy access to an exclusive member’s club here in North Chatham.


We selected the top 3% holiday homes in Massachusetts Airbnb Alternatives

Explore the 916 most perfect homes in our collection

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Most popular homes in Massachusetts

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

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Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Massachusetts to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Massachusetts Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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