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Great Barrington Vacation Rentals with Air Conditioning(63)

63 Results
2 - 3 night minimum stay
  • 5 BR,
  • 2 BA,
  • Sleeps 10
(3)
7 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 11
  • 1 BR,
  • 1 BA,
  • Sleeps 8
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
(3)
14 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
1 Review
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(12)
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
(16)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 Reviews
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 6
2 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
  • 1 BR,
  • 1 BA,
  • Sleeps 4
(10)
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
  • 4 BR,
  • 2 BA,
  • Sleeps 15
(3)
2 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
(11)
$190 - $249
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
(6)
2 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
(9)
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
(17)
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(12)
4 night minimum stay
  • 8 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 18
(4)
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
30 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(29)
3 - 7 night minimum stay
  • 2 BR,
  • Sleeps 6
(13)
$1,500 - $2,000
per week
7 - 14 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(4)
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Recent Great Barrington Reviews

THE BEST DECISION WE MADE FOR OUR WEDDING!

5 of 5
Renting this cozy home was truly the best decision we made for our wedding this summer! It was incredible to be able to have all of our family and friends from out-of-town stay in one place, as opposed to scattered throughout the Berkshires in extremely pricey hotels. The owners of the house were so generous with their belongings that it really made us feel like we were at home. On the night of our wedding, we slept 17 people (using a comfy chair!). It is well laid-out and can house several couples and then many singles. It is also a very short but hilly walk to Main St, Great Barrington. I would highly recommend this house to anyone wanting to spend sometime with a large crowd in the Berkshires!
  • Submitted: Jul 21, 2014
  • Stayed: Jul 2014

BEAUTIFUL, FUNCTIONAL & RELAXING

5 of 5
Our family of 10 stayed for a week in this beautifully kept, functionally designed, spaciously relaxing home. Big family meals happened with ease, naps were taken without interrupting noise, and not a single World Cup game was missed. The house was well supplied including the invitation to partake from the kitchen garden. We spent most of our time outside on the brand new deck and swimming in the clean pool. Very close to town and other area attractions, everyone in the family agreed it was a perfect place to stay.
  • Submitted: Jul 21, 2014
  • Stayed: Jun 2014

FELT LIKE WE WERE IN A COZY TREEHOUSE!

5 of 5
We had the pleasure of staying 4 nights at this cozy, charming apartment and did not want to leave. This spot feels secluded but is close to anything needed, a perfect combination. Lovely home and grounds.
  • Submitted: Jul 16, 2014
  • Stayed: Jul 2014