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The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$722

Ski Cottage in the Berkshire Hills

Stephentown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

Great rentals within 20 miles that match your search

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$153

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$327

Berkshire Farmhouse Vacation

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

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Price per night from

$298

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,863

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$859

Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

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Price per night from

$315

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$818

The Lodge at Fox Hollow

Petersburg house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$338

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

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Price per night from

$344

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$802

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$172

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$196

Chalet near 4 ski resorts with hot tub

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,030

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$682

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$401

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$195

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$172

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$298

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$458

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$744

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$572

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$659

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$567

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$795

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