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Private pool

Heated pool
Private indoor pool
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Private tennis court
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Swing set or jungle gym
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Staffed property
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Pets
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Parking
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Children under 5
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Smoking - Ask
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Skiing – property near ski resort
Walking trips
Tennis in town
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Golf course on site or within 15 min walk
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46 Houses

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The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms
4 bathrooms

sleeps 12

Price per night from

$722

Ski Cottage in the Berkshire Hills

Stephentown house

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$287

The Stephentown Hotel!

Stephentown b&b

2 bedrooms
1 bathroom

sleeps 6

Price per night from

$109

Great rentals within 20 miles that match your search

Iris Room

Stockbridge farmhouse

1 bedroom
1 bathroom

sleeps 2

Price per night from

$172

Horse Room

Stockbridge farmhouse

1 bedroom
1 bathroom

sleeps 3

Price per night from

$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$263

Garfield House

Lee apartment

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$201

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.

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.

Price per night from

$298

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$430

Golden Triangle in the Berkshires

Hancock house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$2,863

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.

Price per night from

$229