Vacation Rentals & House Rentals in Stephentown

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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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28 Houses

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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

$723

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

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

$819

Christmas in The Berkshires

Hancock condo

1 bedroom
2 bathrooms

sleeps 4

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$258

Modern Cozy Wooded Retreat

Spencertown house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$153

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

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