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Stockbridge Ski Vacation Rentals(40)

40 Results
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
(8)
$714 - $825
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(8)
$750 - $857
per night
2 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 16
2 - 7 night minimum stay
(9)
$8,000 - $9,000
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
1 Review
$286 - $600
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(15)
$300 - $400
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night minimum stay
(3)
$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)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 8
  • 1 BR,
  • 1 BA,
  • Sleeps 4
$325 - $357
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
1 Review
$200
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 5
2 night minimum stay
(5)
$250
per night
2 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night minimum stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 30 night minimum stay
(8)
$900 - $3,000
per month
7 - 30 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 - 30 night minimum stay
(3)
$275 - $325
per night
3 night minimum stay
  • 3 BR,
  • Sleeps 6
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 3
2 night minimum stay
(5)
$295
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
2 Reviews
  • 3 BR,
  • 1 BA,
  • Sleeps 5
  • 4 BR,
  • 2 BA,
  • Sleeps 8
  • 2 BR,
  • 3 BA,
  • Sleeps 6
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 10
16 more choices from the HomeAway Network
$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)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
2 Reviews
$3,800 - $6,200
per week
7 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 16
7 night minimum stay
(11)
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Recent Stockbridge Reviews

Excellent winter weekend retreat

5 of 5
We spent two relaxing days at The School House, which is conveniently located near the Taconic and Mass Pike. The well-stocked and enormous kitchen and the great room were the highlights. Only one complaint: The bedrooms do not have shades or curtains, so we were woken up early by the morning light. Mary, thanks for opening up your lovely house to guests!
  • Submitted: Jan 22, 2015
  • Stayed: Jan 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

Exceptional accommodations

5 of 5
Our family, including two adult daughters and 13 month old granddaughter traveled to MA for a family wedding. We wanted accommodations that would allow our granddaughter to nap without everyone having to take one, as we would have in a hotel room. This apartment was perfect. As others have written, the property is clean and the decor inviting. The kitchen is well equipped and we cooked simple meals nightly, buying fresh produce at local farmers' markets. Jane welcomed us when we arrived (nearly three hours earlier than expected), gave us a tour of the grounds and the apartment, and even provided a crib, high chair, and a gate for our granddaughter. She left written information in the apartment to answer what might be called FAQs and answered any questions we had as well. We walked the grounds on several occasions, enjoying the landscaping and the view of the golf course. We visited the Norman Rockwell Museum, Hyde Park, The Mount and the home of Martin Van Buren while in the area. We would definitely recommend this property to friends or relatives visiting the area, and if we ever return to MA, we'll return here.
  • Submitted: Sep 21, 2014
  • Stayed: Sep 2014