Become a host

Book Luxury Monthly Rentals in Massachusetts

We selected the 39 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.

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.

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.

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.

We selected the top 3% holiday homes in Massachusetts Monthly Rentals

Explore the 39 most perfect homes in our collection

View on map

Most popular homes in Massachusetts

The Lakehouse

The Lakehouse

  • 10 guests

  • 4 bedrooms

Morris, Litchfield

The Golden Dawn

The Golden Dawn

  • 4 guests

  • 2 bedrooms

Litchfield, Litchfield County

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

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

The Rainbow Bird

The Rainbow Bird

  • 8 guests

  • 4 bedrooms

Woodbury, Litchfield County

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

View all

Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Massachusetts, United States, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Massachusetts Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

Search Our Collection

  1. Plum Guide

  2. United States

  3. Massachusetts

  4. Monthly Rentals