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Massachusetts Ski Cottage Rentals(73)

73 Results
$1,295 - $2,100
per week
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 - 7 night minimum stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(18)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 7 night minimum stay
(12)

Why HomeAway?

We're the leader in vacation rentals
More than one million listings worldwide
Experienced property owners or managers
Average five years in the business
$475 - $500
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
$125 - $150
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
2 Reviews
$400 - $650
per night
2 - 13 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 13 night minimum stay
(17)
$300
per night
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(4)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(5)
  • 4 BR,
  • Sleeps 6
2 night minimum stay
(16)
$165 - $185
per night
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(25)

Why HomeAway?

We help you travel with confidence
Every listing guaranteed against fraud
We offer a best price guarantee
No booking fees and low online prices
$175 - $571
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(23)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(7)
$135 - $195
per night
2 - 4 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(6)
$155 - $200
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 2 night minimum stay
(9)
$129 - $189
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(20)
$225 - $250
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(3)
$169 - $275
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night minimum stay
(28)
$200 - $225
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(10)
$165 - $180
per night
3 - 4 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 4 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 5
$175 - $249
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 - 2 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(9)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(3)
$83 - $199
per night
2 - 90 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 4
2 - 90 night minimum stay
(14)
  • 2 BR,
  • Sleeps 4
7 night minimum stay
(5)
$1,505
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(5)
$200 - $250
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 8
2 night minimum stay
(21)
$1,100 - $1,505
per week
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 7 night minimum stay
(9)
$1,000
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
7 night minimum stay
(6)
 

Recent Massachusetts Reviews

Cozy and relaxing

4 of 5
I enjoyed staying at this property very much. As returner customers, my boyfriend and I really liked our visit this time. We loved the house and felt very relaxed and comfortable. We enjoyed the amenities as well as the layout of the house and look forward to returning next year!
  • Submitted: Jan 14, 2015
  • Stayed: Dec 2014

Perfectly adorable cottage!

5 of 5
We stayed here for 3 nights in September and absolutely loved the cottage from the moment we arrived. It is clean, spacious and decorated so nicely. It was a little home away from home. The location is 3 minutes drive to main downtown area of Great Barrington. Plenty of outdoor space to enjoy a morning coffee and let our dog run around. Quietly tucked in a neighborhood, but so close to shops and restaurants. Shana was wonderful and so easy to communicate with. We plan to return again next year and would recommend to couples and families.
  • Submitted: Nov 1, 2014
  • Stayed: Sep 2014

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