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Berkshires Vacation Rentals with pool(30)

30 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
1 - 2 night min stay
(7)
$549 - $949
per night
2 - 4 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 15
2 - 4 night min stay
(19)
$3,500 - $8,000
per month
30 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
30 night min stay
1 Review
$625 - $1,000
per week
7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night min stay
(6)
$100 - $193
per night
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
(16)
$1,500 - $2,350
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(3)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 night min stay
(12)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
2 Reviews
$245 - $275
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
$300
per night
2 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night min stay
(3)
  • 7 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(14)
  • 6 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(3)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
  • 8 BR,
  • 5 BA,
  • Sleeps 16
1 Review
$500 - $600
per night
2 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 11
2 night min stay
(6)
$600 - $671
per night
2 - 7 night min stay
  • 6 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night min stay
(5)
$900 - $1,200
per night
2 - 4 night min stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 4 night min stay
(4)
$770 - $1,800
per week
7 - 14 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night min stay
2 Reviews
$1,350 - $1,750
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(9)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 night min stay
$275 - $425
per night
4 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night min stay
$300 - $500
per night
3 - 30 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
3 - 30 night min stay
(3)
$750
per night
3 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 18
3 night min stay
(3)
  • 6 BR,
  • 5 BA,
  • Sleeps 14
30 - 31 night min stay
2 Reviews
$3,000 - $6,000
per week
7 - 14 night min stay
  • 4 BR,
  • 1 BA,
  • Sleeps 14
7 - 14 night min stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(4)
$325 - $425
per night
3 - 5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(4)
$750 - $1,000
per night
3 - 6 night min stay
  • Studio,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 6 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
 

Recent Berkshires Reviews

Perfect Getaway for Cousins Club Weekend!

5 of 5
We were in search of a large house that could accommodate many families for our cousins club weekend and the Berkshire Country Estate was the perfect find! Plenty of room for families to have their own space but also convene together for dining and game playing. We were all very comfortable in this beautiful, charming home and the owners were a pleasure to deal with and very welcoming. The house is well equipped with cooking utensils and a grill so it was easy to eat in as a family. Also, the game room was a big plus for the kids (they loved the air hockey and pin ball machine) and the outside swing set and basketball hoop were a plus and we all enjoyed ping pong in the barn. We even had a family kick ball game on the large yard. I know there are plenty of sightseeing opportunities close to this property but the house was so great, we never left for the weekend! Thank you for a memorable weekend and we look forward to returning:)
  • Submitted: Nov 13, 2014
  • Stayed: May 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