81 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Berkshires Rentals(81)

81 Results
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
7 night minimum stay
(3)
$1,750 - $2,100
per week
14 - 30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
14 - 30 night minimum stay
$155 - $185
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(16)
$125 - $150
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
2 Reviews
$475 - $500
per night
2 - 3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 3 night minimum stay
$175
per night
4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
4 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 14
$400 - $650
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 7 night minimum stay
(17)
$300
per night
4 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
4 - 7 night minimum stay
(4)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(5)
$1,000
per night
2 night minimum stay
  • 5 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 12
2 night minimum stay
  • 4 BR,
  • Sleeps 6
2 night minimum stay
(16)
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
(7)
$135 - $195
per night
2 - 4 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 4 night minimum stay
(6)
$135 - $200
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 2 night minimum stay
(9)
$129 - $189
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(20)
$250
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
2 night minimum stay
(7)
$200
per night
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
2 Reviews
$169 - $275
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
2 - 7 night minimum stay
(28)
$200 - $225
per night
2 - 3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night minimum stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 5
$175 - $249
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 - 2 night minimum stay
(8)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night minimum stay
(10)
$83 - $199
per night
2 - 90 night minimum stay
  • 2 BR,
  • 1 BA,
  • 2 HF BA,
  • Sleeps 4
2 - 90 night minimum stay
(14)
$1,505
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
7 night minimum stay
(5)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(3)
$1,100 - $1,505
per week
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
2 - 7 night minimum stay
(9)
$150
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(3)
 

Recent Berkshires Reviews

Tucked away Sanctuary

5 of 5
Absolutely Perfect! This sweet cottage is quaint yet quite accommodating with plenty of amenities and activities for everyone. No need to bring anything except your clothes, spirit and food. Upon arrival, the coffee was set, soft music was playing and candles were lit. I found this to be a nice little added touch. We immediately brewed our coffee and took a walk to the lake, which is a stones throw away , and enjoyed the natural beauty and crisp fresh air while sipping coffee and taking it all in. If your looking to be rejuvenated, then this is the place for you. Scott is such a good host and clearly takes pride in making his cottage feel warm and inviting to his guest. He is reasonably priced, accommodating and available by phone if you have any questions.
  • Submitted: Jan 29, 2015
  • Stayed: Jan 2015

Cozy and relaxing

4 of 5
I enjoyed staying at this property very much. As returner customers, my boyfriend and I really liked our visit this time. We loved the house and felt very relaxed and comfortable. We enjoyed the amenities as well as the layout of the house and look forward to returning next year!
  • Submitted: Jan 14, 2015
  • Stayed: Dec 2014

Perfectly adorable cottage!

5 of 5
We stayed here for 3 nights in September and absolutely loved the cottage from the moment we arrived. It is clean, spacious and decorated so nicely. It was a little home away from home. The location is 3 minutes drive to main downtown area of Great Barrington. Plenty of outdoor space to enjoy a morning coffee and let our dog run around. Quietly tucked in a neighborhood, but so close to shops and restaurants. Shana was wonderful and so easy to communicate with. We plan to return again next year and would recommend to couples and families.
  • Submitted: Nov 1, 2014
  • Stayed: Sep 2014