Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Barns
Cabins
Cottages
Estates
Homes
Apartments
Boats
Bungalows
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Berkshires Vacation Rentals with Pool(29)

29 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
(7)
$449 - $949
per night
2 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 15
2 - 3 night minimum stay
(19)
$500
per night
6 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 night minimum stay
2 Reviews
  • 4 BR,
  • 3 BA,
  • Sleeps 9
1 Review
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 18
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 30 night minimum stay
(11)
$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
$1,500 - $2,350
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 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 6
3 - 6 night minimum stay
1 Review
$1,000
per week
7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
7 night minimum stay
(6)
$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
$300
per night
2 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night minimum stay
(3)
  • 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
13 more choices from the HomeAway Network
$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)
$900 - $1,100
per night
2 - 3 night minimum stay
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 3 night minimum stay
(8)
$1,200 - $1,750
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
2 Reviews
  • 6 BR,
  • 5 BA,
  • Sleeps 14
2 - 31 night minimum stay
2 Reviews
$1,350 - $1,650
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(9)
$2,000 - $2,500
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 night minimum stay
  • 6 BR,
  • 6 BA,
  • 1 HF BA,
  • Sleeps 18
(4)
$300 - $500
per night
3 - 30 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
3 - 30 night minimum stay
(3)
$750 - $850
per night
3 - 5 night minimum stay
  • Studio,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 5 night minimum stay
$275 - $425
per night
3 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night minimum stay
(3)
  • 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