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               Berkshires (14 properties)

Berkshires Ski Chalets

Select a location below to drill down, or click on a property image to see the ski chalets in Berkshires that we have to offer.
Becket  Savoy  Tolland 
Great Barrington  Stockbridge  West Stockbridge 
Monterey 

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properties that :

  • Family Friendly:

  • Non Smoking:

  • Permit Pets:

  • Are Near Golf:

  • Have a Calendar:

  • Have Air Conditioning:

  • Are Near a Beach:

  • Accept Credit Cards:

  • Have Disabled Access:

  • Have Internet Access:

  • Near Public Transport:

  • Near Bars & Restaurants:

  • Have A Pool:

  • Are Near Skiing:






House in Great Barrington, near skiing. Sleeps 10-12 People
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House in Great Barrington, near skiing. Sleeps 10-12 People

Large Great Barrington Contemporary

Great, private Contemporary within a short distance to the down-town shoping, restaurants and Triplex Cinema.

bedrooms  4    bathrooms3
sleeps 10 - 12

$3500 - $6800
Per Month
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Golf Course Nearby Pets Allowed Has Availability Calendar No Air Conditioning Beach Nearby Credit Cards Not Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is not Family Friendly Does Not Have Location Map     
House in Berkshires, near skiing. Sleeps 6-6 People
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House in Berkshires, near skiing. Sleeps 6-6 People

Bershire Rental w/Lakefront property

Ranch house with lakefront access in Cheshire.

bedrooms  3    bathrooms2
sleeps 6

$100 - $150
Per Day
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Not Near A Beach Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Cabin in Tolland, near skiing. Sleeps 8-8 People
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Cabin in Tolland, near skiing. Sleeps 8-8 People

Log Cabin Rental on a small Lake

Situated in a private vacation community located on a dead end street with direct frontage on a 74 Acre Lake.

bedrooms  3    bathrooms2
sleeps 8

$1500 - $2000
Per Week
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Golf Course Nearby Pets Allowed Does Not Have Availability Calender Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Not Near Bars or Restaurants Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
House in Berkshires, near skiing. Sleeps 1-8 People
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House in Berkshires, near skiing. Sleeps 1-8 People

Apple Valley Log Cabin

Find your budget-friendly, quality stay-cation at this 1800 sq.ft Log Cabin Home on 6 very private, wooded acres!

bedrooms  3    bathrooms1
sleeps 1 - 8

$160 - $205
Per Day
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Golf Course Nearby Pets Allowed Has Availability Calendar No Air Conditioning Beach Nearby Credit Cards Accepted Not Non-Smoking Disabled Access Has Internet Access No Public Transport Nearby Not Near Bars or Restaurants Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Bed and Breakfast in West Stockbridge, near skiing. Sleeps 20-30 People
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Bed and Breakfast in West Stockbridge, near skiing. Sleeps 20-30 People

Shaker Mill Inn, West Stockbridge

Luxurious efficiency suite lodging at affordable prices.

bedrooms  9    bathrooms9
sleeps 20 - 30

$100 - $480
Per Day
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Golf Course Nearby Pets Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Cottage in Becket, near skiing. Sleeps 4-6 People
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Cottage in Becket, near skiing. Sleeps 4-6 People

lake front cottage in the berkshires

lake front cottage on private non motorboat lake

bedrooms  2    bathrooms1
sleeps 4 - 6

$150 - $150
Per Day
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Golf Course Nearby Pets Not Allowed Does Not Have Availability Calender No Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Cottage in Monterey, near skiing. Sleeps 6-6 People
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Cottage in Monterey, near skiing. Sleeps 6-6 People

Lovely waterfront Cottage in Monterey

Charming Lake Garfield waterfront Cottage at the premier Berkshire location in the enchanted Monterey, MASS.

bedrooms  4    bathrooms2
sleeps 6

$1800 - $2500
Per Week
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Golf Course Nearby Pets Allowed Does Not Have Availability Calender No Air Conditioning Beach Nearby Credit Cards Not Accepted Not Non-Smoking Not Disabled Friendly Does Not Have Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is not Family Friendly Does Not Have Location Map     
House in Becket, near skiing. Sleeps 6-6 People
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House in Becket, near skiing. Sleeps 6-6 People

Newly Built Home with lots of light

Newly built home with lots of natural light, gourmet kitchen, close to private lake.

bedrooms  3    bathrooms3
sleeps 6

$4500 - $4500
Per Month
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
House in Stockbridge, near skiing. Sleeps 6-6 People
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House in Stockbridge, near skiing. Sleeps 6-6 People

SPECTACULAR HOME ON YOUR OWN PRIVATE SMALL LAKE

bedrooms  3    bathrooms3
sleeps 6

$2000 - $3500
Per Week
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Golf Course Nearby Pets Not Allowed Has Availability Calendar Has Air Conditioning Beach Nearby Credit Cards Not Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Cabin in Savoy, near skiing. Sleeps 6-8 People
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Cabin in Savoy, near skiing. Sleeps 6-8 People

The Cabin at Nine Black Brook

Tucked away in the beautiful Berkshire village of Savoy, Massachusetts, this well-appointed cabin is perfect!

bedrooms  2    bathrooms1
sleeps 6 - 8

$900 - $1000
Per Week
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Not Near A Golf Course Pets Allowed Has Availability Calendar No Air Conditioning Not Near A Beach Credit Cards Accepted Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Not Near Bars or Restaurants Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     
Manor in Becket, near skiing. Sleeps 8-10 People
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Manor in Becket, near skiing. Sleeps 8-10 People

Colesbrook Manor

Shingle style, timber frame, Berkshire cottage,a retreat destination any time of year..Woods and stream

bedrooms  4    bathrooms2
sleeps 8 - 10

$250 - $250
Per Day
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Golf Course Nearby Pets Not Allowed Has Availability Calendar No Air Conditioning Beach Nearby Credit Cards Not Accepted Not Non-Smoking Not Disabled Friendly Has Internet Access No Public Transport Nearby Bars or Restaurants Close By Does Not Have A Pool Skiing Close By Is Family Friendly Has Location Map     

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