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15 Houses

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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.

Match: Walking trips Water sports

All filters match

Price per night from

$487

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Walking trips Water sports

All filters match

Price per night from

$251

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.

Match: Walking trips Water sports

All filters match

Price per night from

$234

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Walking trips Water sports

All filters match

Price per night from

$327

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Walking trips Water sports

All filters match

Price per night from

$261

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Walking trips Water sports

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: Walking trips Water sports

All filters match

Price per night from

$70

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CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Walking trips, Water sports

1 of 2 filters match

Price per night from

$282

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

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 of 2 match: Water sports, Walking trips

1 of 2 filters match

Price per night from

$795

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Water sports, 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: Water sports, Walking trips

1 of 2 filters match

Price per night from

$98

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Water sports, Walking trips

1 of 2 filters match

Price per night from

$568

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

1 of 2 match: Walking trips, Water sports

1 of 2 filters match

Price per night from

$820

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, Water sports

1 of 2 filters match

Price per night from

$802

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Water sports

1 of 2 filters match

Price per night from

$126

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