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Stockbridge Vacation Rentals(31)

31 Results
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
(9)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(10)
$750 - $857
per night
2 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 16
2 - 7 night minimum stay
(9)
$714 - $825
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(8)
$286 - $600
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(15)
$275
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 night minimum stay
(7)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(11)
$325 - $375
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night minimum stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
1 Review
$250 - $286
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(6)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 30 night minimum stay
(8)
$275 - $325
per night
3 night minimum stay
  • 3 BR,
  • Sleeps 6
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 4
7 night minimum stay
$596 - $836
per week
7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
$596 - $691
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
$608 - $944
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
$620 - $1,232
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$450
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
$219 - $400
per night
1 - 3 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
1 - 3 night minimum stay
(8)
$1,000
per night
4 night minimum stay
  • 6 BR,
  • 6 BA,
  • Sleeps 12
4 night minimum stay
(5)
$250 - $300
per night
2 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night minimum stay
(7)
$225 - $330
per night
2 - 7 night minimum stay
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 7
2 - 7 night minimum stay
(7)
$3,800 - $6,200
per week
7 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 16
7 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
(3)
$250 - $300
per night
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
$1,750 - $2,100
per week
14 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
14 - 30 night minimum stay
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Recent Stockbridge Reviews

Ultra Charming Berkshire getaway!

5 of 5
We were pleasantly surprised at how cozy this house was, yet big enough for two families to stay together. Beautiful design aesthetic throughout the rooms. The day bed room was perfect for our two little kids and the master is huge and inviting. The house is fully stocked with much more than most houses we have rented and the owner was pleasant and very accommodating. The house is centrally located in the heart of the Berkshires. We spent our days snowboarding just 1/2 hour from Jiminy Peak, 15 from Butternut, and Bousquet is just a few minutes away. And spent our nights eating at the great restaurants in Stockbridge, West Stockbridge, Lenox and Great Barrington. Norman Rockwell museum just down the road is an american treasure, while antique stores and quaint browse around stores are nearby as well. Highly recommend this house for a Berkshire getaway.
  • Submitted: Feb 22, 2015
  • Stayed: Feb 2015

A Wonderful Place to Enjoy with Family and Friends

5 of 5
My family was thrilled to find such a beautiful, spacious, and well-equipped home in which to stay during our children's school vacation. Mary is a gracious hostess who has her guests' needs in mind. There is so much to do, so close to her marvelous, restored school house. We certainly plan to return in the future.
  • Submitted: Feb 20, 2015
  • Stayed: Feb 2015

Luxury and space in idyllic surroundings

5 of 5
The cottage was beautiful, with every convenience. Ruth and Gareth, the owners in the house next door, had thoughtfully provided a comprehensive supply of food and drink items to ease us into the evening and our first breakfast. They were also more than helpful when we had a problem operating the drier, and quickly dried our things themselves. The gardens around the house were lovely with views of the river. The Red Lion Inn is a beautiful old place with lots of interesting curios and fantastic food. We also ate extremely well at Once Upon a Table just a few yards further down Main Street. When you stay here you must make time to visit the Norman Rockwell Museum and the Shaker Village (food was great here too) Both of which are superb. I have already recommended the cottage and area to friends and colleagues.
  • Submitted: Oct 16, 2014
  • Stayed: Sep 2014