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27 Houses

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Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Great rentals within 20 miles that match your search

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

$347

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$173

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$341

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$262

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$569

Balcony Room in Victorian 2 minutes walk to delightful Shelburne Falls center.

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$144

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$173

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

$798

Sadawga Springs Retreat

Whitingham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$403

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$196

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$173

Welcome to the Blooming Inn Shelburne Falls, AKA Dancing Bear Guest House Twin

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$98

Cute two bedroom

Williamsburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$138

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$344

Responds fast! avg. 1 hour 45 minutes

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$122

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$263

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$196

Flight's End-A Country Home with Babbling Brook

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

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Price per night from

$218

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$430

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,863

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

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$234

Gartner House, a charming home in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

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Price per night from

$229

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

Charming Affordable Home for groups up to 14

Shelburne Falls house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

“Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.

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Price per night from

$573

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

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