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Berkshires Vacation Rentals with Pool(28)

28 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
(5)
$449 - $949
per night
2 - 4 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 15
2 - 4 night minimum stay
(18)
  • 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)
  • 14 BR,
  • 9 BA,
  • 2 HF BA,
  • Sleeps 30
2 - 7 night minimum stay
1 Review
$900 - $1,071
per night
2 - 7 night minimum stay
  • 10 BR,
  • 7 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 7 night minimum stay
$300
per night
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night minimum stay
(3)
$100 - $193
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
(16)
  • 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
12 more choices from the HomeAway Network
$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)
$425 - $543
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
  • 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)
$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)
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(4)
$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

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

Amazing Cycling Getaway

5 of 5
We thought we would take this opportunity to say how much we enjoyed our stay at the Berkshire Estate. This estate has it all. Some of the highlights of the estate include; beautiful pool, separate building complete with table tennis, workout room, numerous fireplaces, beautiful bedrooms, games room with pinball, secluded location, and so many more amenities that they are impossible to list. The entire estate is furnished with period pieces that very much add to the ambiance. The purpose for our visit to the region was primarily cycling but the Berkshire Estate is perfect for any large group looking for a pampered stay.
  • Submitted: May 26, 2014
  • Stayed: May 2014