Massachusetts Ski Resort Rentals

We selected the 5 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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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, Berkshire County

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

The Northstar

The Northstar

  • 6 guests

  • 3 bedrooms

Placer County, California

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

Riding High

Riding High

  • 4 guests

  • 2 bedrooms

Mountain Village, San Miguel County

Snowy Shoes

Snowy Shoes

  • 4 guests

  • 2 bedrooms

Mountain Village, San Miguel County

The Glow Of The Mountain

The Glow Of The Mountain

  • 4 guests

  • 3 bedrooms

Lake County, Colorado

Snowfall Lullaby

Snowfall Lullaby

  • 4 guests

  • 1 bedrooms

Snowmass Village, Pitkin County

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Check upcoming rates & availability for Massachusetts Ski Resort Rentals


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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