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48 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: Tennis in town Children under 5

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Price per night from

$487

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

Match: Tennis in town Children under 5

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Price per night from

$815

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.

Match: Tennis in town Children under 5

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Price per night from

$297

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Tennis in town Children under 5

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Price per night from

$799

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Tennis in town Children under 5

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Price per night from

$262

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Tennis in town Children under 5

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Price per night from

$326

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Tennis in town Children under 5

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Price per night from

$565

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Garfield House

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$200

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: Tennis in town, Children under 5

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Price per night from

$371

Escape to the Berkshires!

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 11 minutes

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$314

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$428

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$856

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$2,852

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$856

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$257

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$571

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$343

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$172

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$337

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$400

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$280

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$679

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

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Price per night from

$109

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

1 of 2 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

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$81

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$172

Responds fast! avg. 1 hour 31 minutes

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$122

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$744

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$458

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$659

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$172

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$172

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: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$170

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$114

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$217

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$97

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Tennis in town, Children under 5

1 of 2 filters match

Price per night from

$172

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