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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

$724

Ski Cottage in the Berkshire Hills

Stephentown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$287

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$109

Great rentals within 20 miles that match your search

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

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$263

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$820

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$259

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$153

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.

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Price per night from

$373

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

$299

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$431

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,868

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

$230

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

$861

The Lodge at Fox Hollow

Petersburg house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$339

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

$345

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

$197

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

$1,032

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$402

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$261

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$299

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

Garfield House

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$201

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$567

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$682

Charming Guest Suite

Old Chatham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$155

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

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Price per night from

$315

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

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$195

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

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

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$81

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