Massachusetts Unique Homes

We selected the 40 homes worth renting in this location

Home spotlights in Massachusetts

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.

The Old Silo

The Old Silo

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Formerly a grain silo, this extraordinary house is as unique and beautiful as its surroundings. Set on 170 acres of rolling green New England countryside, there are breathtaking views from all sides.

A Little Love Note

A Little Love Note

  • 6 guests

  • 2 bedrooms

New Lebanon, New York

Surrounded by acres of forest, flowing streams, waterfalls and historic ruins, this little cottage welcomes you to experience the natural beauty of the Berkshire mountains. Located within a former Shaker settlement, there’s an abundance of charm and character here.

Ode to the Past

Ode to the Past

  • 10 guests

  • 5 bedrooms

New Lebanon, New York

When you want to get away from the hustle and bustle, this New Lebanon home is the perfect choice. You’ll not only leave the hectic city behind – stepping through the doors feels a little like stepping back in time.


We selected the top 3% holiday homes in Massachusetts Unique Homes

Explore the 40 most perfect homes in our collection

View on map


Most popular homes in Massachusetts

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Sail of the Century

Sail of the Century

  • 16 guests

  • 6 bedrooms

Stonington, Connecticut

The Tree House

The Tree House

  • 6 guests

  • 3 bedrooms

Egremont, Hillsdale

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

Pondering Soul

Pondering Soul

  • 14 guests

  • 7 bedrooms

Copake, New York

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket, Nantucket County

Upstate Serenity

Upstate Serenity

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

View all



Frequently asked questions

Plum guide offers a handpicked selection of the most unique homes in Massachusetts, United States. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and secure the most unique home in Massachusetts, United States for your next getaway. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

Search Our Collection