Massachusetts Ski Resort Rentals

We selected the 5 homes worth renting in this location

Home spotlights

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

It’s no wonder why a multitude of actors, composers, and artists have hideaways in the Berkshires. This classic Berkshires home, originally built as a schoolhouse in 1866, is steeped in history and rural charm.

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.

Pondering Soul

Pondering Soul

  • 14 guests

  • 7 bedrooms

Copake, New York

Designed by a renowned architect, and tastefully furnished, this award-winning home is built for coming together for quality time spent as a group, while still allowing guests ample privacy. Enjoy blissful peace and serenity amidst the 45 private acres of rolling hills and large ponds that surround the property.

The Berkshires Splendour

The Berkshires Splendour

  • 12 guests

  • 6 bedrooms

New Marlborough, Massachusetts

Nature meets luxury at this stunning Berkshire Mountain retreat. Just twenty minutes from Great Barrington and with hiking trails all around, this home is an idyllic escape from the hustle and bustle.


We selected the top 3% holiday homes in Massachusetts Ski Resort Rentals

Explore the 5 most perfect homes in our collection

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Most popular homes

Ponder & Wander

Ponder & Wander

  • 12 guests

  • 4 bedrooms

Wilmington, Windham County

Snow Park

Snow Park

  • 14 guests

  • 6 bedrooms

Snowmass Village, Pitkin County

Lucky Denver Mint

Lucky Denver Mint

  • 2 guests

  • 1 bedrooms

Lower Highland, Denver

Mountain Glacier

Mountain Glacier

  • 6 guests

  • 3 bedrooms

Flathead County, Montana

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Soaring Skies

Soaring Skies

  • 8 guests

  • 3 bedrooms

El Dorado County, California

Green Grass of Home

Green Grass of Home

  • 4 guests

  • 2 bedrooms

Carbondale, Garfield County

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Frequently asked questions

Explore our collection of ski resort rentals in Massachusetts, United States. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best ski resort rentals that Massachusetts, United States has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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