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33 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: Air conditioning Walking trips

All 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.

Match: Air conditioning Walking trips

All filters match

Price per night from

$234

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Air conditioning Walking trips

All filters match

Price per night from

$260

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Air conditioning 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: Air conditioning 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: Air conditioning Walking trips

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Price per night from

$81

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

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

1 of 2 match: Air conditioning, 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: Air conditioning, 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: Air conditioning, 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: Air conditioning, Walking trips

1 of 2 filters match

Price per night from

$327

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Air conditioning, Walking trips

1 of 2 filters match

Price per night from

$251

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$338

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$172

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$401

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$344

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$115

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$172

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$458

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$126

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$263

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$373

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$430

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$2,863

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$171

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$722

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Walking trips, Air conditioning

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, Air conditioning

1 of 2 filters match

Price per night from

$572

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$686

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$744

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$818

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$573

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Walking trips, Air conditioning

1 of 2 filters match

Price per night from

$659

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, Air conditioning

1 of 2 filters match

Price per night from

$802

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