Book Luxury Vacation Rentals in Massachusetts

Award-winning homes from £98

Home spotlights in Massachusetts

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.

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.

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

A nature lover's dream atop a 100-acre historic farm in North Stonington, away from the hustle and bustle of everyday life. This home offers a one-of-a-kind stay – spend your mornings in the fresh air helping the hosts tend to the farm animals in the tranquil setting to feel at one with nature – from feeding chickens and collecting eggs to brushing the horses and rooster calls here and there, but it's all part of the experience.

World Series

World Series

  • 2 guests

  • 1 bedrooms

West Fens, Boston

As studio apartments go, this one is pretty special. Set high up in a gleaming glass building, the fantastic views over Boston will draw you in and we guarantee you'll feel on top of the world during your stay.


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

Explore the 19 most perfect homes in our collection

View on map

Most popular homes in Massachusetts

Swing For The Fences

Swing For The Fences

  • 2 guests

  • 1 bedrooms

West Fens, Boston

Take Me Out To The Ball Game

Take Me Out To The Ball Game

  • 2 guests

  • 1 bedrooms

West Fens, Boston

Stone & Glass

Stone & Glass

  • 4 guests

  • 2 bedrooms

West Fens, Boston

One If By Land

One If By Land

  • 2 guests

  • 1 bedrooms

Beacon Hill, Boston

Leading Lights

Leading Lights

  • 2 guests

  • 1 bedrooms

Beacon Hill, Boston

Where Everybody Knows Your Name

Where Everybody Knows Your Name

  • 2 guests

  • 1 bedrooms

Back Bay West, Boston

The Boston Beauty

The Boston Beauty

  • 2 guests

  • 1 bedrooms

Back Bay West, Boston

The Heart of the Square

The Heart of the Square

  • 2 guests

  • 1 bedrooms

Central Square, Cambridge

View all


Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Massachusetts, United States. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Massachusetts Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

Search Our Collection