Book Luxury Airbnb Alternatives in Massachusetts

We selected the 918 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.

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment.

On the Edge of Nature

On the Edge of Nature

  • 4 guests

  • 3 bedrooms

Gardiner, New York

It’s the end of the line. Beyond this chalet, there’s nothing but Minnewaska’s protected preserveland.

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 918 most perfect homes in our collection

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Most popular homes in Massachusetts

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

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

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

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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