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Berkshires Vacation Rentals with Pool(30)

30 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 9
1 Review
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 18
$600 - $1,000
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
(5)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 30 night minimum stay
(9)
$1,500 - $2,350
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(3)
$1,900 - $1,993
per night
2 - 7 night minimum stay
  • 14 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 30
2 - 7 night minimum stay
1 Review
$1,400 - $1,429
per night
2 - 7 night minimum stay
  • 10 BR,
  • 7 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 7 night minimum stay
$100 - $193
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(16)
$300
per night
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 night minimum stay
$500
per night
6 - 10 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 night minimum stay
2 Reviews
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(14)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
2 night minimum stay
2 Reviews
  • 8 BR,
  • 5 BA,
  • Sleeps 16
1 Review
14 more choices from the HomeAway Network
  • 3 BR,
  • 2 BA,
  • Sleeps 8
90 night minimum stay
$900 - $1,100
per night
2 - 3 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 3 night minimum stay
(7)
$217 - $500
per night
2 - 30 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 11
2 - 30 night minimum stay
(6)
$600 - $671
per night
2 - 7 night minimum stay
  • 6 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(5)
$199 - $340
per night
2 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 22
2 night minimum stay
$750 - $850
per night
3 - 5 night minimum stay
  • Studio,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 5 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 14
2 - 31 night minimum stay
1 Review
$1,350 - $1,650
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(8)
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(4)
$750
per night
3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 18
3 night minimum stay
(3)
$275 - $425
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(3)
$2,500
per month
7 - 30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 - 30 night minimum stay
2 Reviews
$300 - $500
per night
3 - 30 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
3 - 30 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
 

Recent Berkshires Reviews

A Perfect Getaway!

5 of 5
A large group of us had a wonderful stay at the Berkshire Country Estate. From owner, house, region and even staff, everything was perfect: 1. We are a group of college friends from 20 years ago and our families. We started with 5 families (15 people) but ended 6 families (18 people). I was afraid we had to find another property. Owner Laurie was so gracious and accommodating that our large group was finally able to enjoy the beautiful place we were looking forward to. She and I had numerous phone and email exchanges to pan out details. I was truly impressed with her professionism as well as flexibility. 2. While owner unable to receive us due to other engagement, she made sure all details informed to us upon our arrival, even arranged her staff to give us a tour to the gigantic house (very much needed. :) ). After our arrival, she even emailed me right back when we needed directions and information regarding surrounding area 3. Needless to say, the house is gigantic :) . Owner was very considerate and arranged extra beds and towels for our large group. Inside of the house has everything to entertain adults and kids. Kitchen has utensils to cook and feed an army. We, a group of 18 only used a portion of them.:) Outside of the house is just as impressive. First day we arrived in afternoon, we couldn't wait and explored the beautiful foliage, trails and woods right at the property 4. Plus the region is as beautiful as it can be in Autumn. OOMS Conservation Area is 2 miles from the house. Its paradise setting made time freeze. Albany and Tanglewood are not far away for those in the group who had never been in the area. Wish we had more time to explore more. some of us in the group hadn't seen each other since college, so the reunion was imaginably memorable. The owner, property and region added nothing but positive experience to the exciting occasion. It was a perfect time for all of us. Would love to go back when similar occasions rise again. Highly recommended. Thank you, Laurie.
  • Submitted: Oct 22, 2014
  • Stayed: Oct 2014

Perfect family getaway

5 of 5
This was the perfect summer getaway for our family. The house was spacious, yet cozy and comfortably accommodated three couples and an infant. Each couple had their own room and bathroom, and enough privacy (even the one in the loft space). The living space was great, kitchen had everything we needed and the pool was clean, well-maintained and perfect for the sunny days. We spent almost every meal on the large deck, dining outdoors and grilling. The view from this house, located atop a hill, was fantastic. You could see for miles across farmlands towards the mountains. The location of the house was also great. It felt secluded and private. It was a short or moderate drive to cute towns like Hudson and Great Barrington, farms/farmers markets, grocery stores, shops, hikes, etc. Also, it was just under a three hour drive from NYC. Alan was a lovely host, checking in with us periodically to ensure we had everything we needed and that we were enjoying our vacation. Our family could not have asked for a better experience for our summer getaway, and we will certainly be returning again!
  • Submitted: Aug 21, 2014
  • Stayed: Aug 2014

Third Time Back

5 of 5
Obviously, three times renting, means we like it a lot! Quiet area, comfortable cottage, very nice owner, good fishing and golf. What else is there to say!
  • Submitted: Jul 14, 2014
  • Stayed: Jun 2014