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23 Houses

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

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

Match: Balcony or terrace Walking trips

All filters match

Price per night from

$795

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Balcony or terrace Walking trips

All filters match

Price per night from

$567

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace Walking trips

All filters match

Price per night from

$70

Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Balcony or terrace Walking trips

All filters match

Price per night from

$81

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The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$109

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$98

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$327

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$261

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$251

Hillhouse Log Cabin

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$487

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.

1 of 2 match: Balcony or terrace, Walking trips

1 of 2 filters match

Price per night from

$234

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$682

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$263

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$259

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$431

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$281

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$572

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$572

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$126

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$820

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$218

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, Balcony or terrace

1 of 2 filters match

Price per night from

$802

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