Cheshire, MA
Berkshires

Shady Pine

Cheshire, MA
๐Ÿ›
6
bedrooms
๐Ÿšฟ
3
baths
๐Ÿ‘ฅ
14
sleeps
๐Ÿ“…
2
min night

Shady Pine is nestled on an idyllic 4-acre property and features a gigantic heated 50โ€™x25โ€™ pool, hot tub, fire pit and more. Being central within the Berkshires means local attractions such as Tanglewood, skiing at Jiminy Peak, and MASS MoCA are only a short-drive away.

Amenities

๐Ÿ“ถ
WiFi
๐Ÿ›
Hot Tub
๐ŸŽฎ
Game Room
๐Ÿ”ฅ
Fire Pit
๐Ÿณ
Full Kitchen
๐Ÿš—
Free Parking
โ™จ๏ธ
Heated Pool
โ„๏ธ
AC
๐Ÿ 
Covered Porch
๐ŸŽฒ
Yard Games

House Rules

No smoking
No parties or events
Pets welcome (fee applies)
Check-in: 4:00 PM
Checkout: 10:00 AM
Quiet hours: 10 PM-8 AM

What guests say

โ˜…ย ย 5.0
โ˜…โ˜…โ˜…โ˜…โ˜…

"We had a great stay and would definitely come back. There is a ton of space for multiple families and it would be great any time of the year. Very clean, and Doreen was quick to respond. Highly recommend!"

j
Jon
Shady Pine ยท 2024
โ˜…โ˜…โ˜…โ˜…โ˜…

"We had a wonderful stay! The house was incredibly spacious with a warm, homey feel. Our kids absolutely loved it and are already asking when we can come back, we're hoping to make this an annual tradition. Highly recommend!"

d
Daniel
Shady Pine ยท 2024
โ˜…โ˜…โ˜…โ˜…โ˜…

"We had a really great time! The house is beautiful and unique, the location quiet and peaceful, and it fit the photos perfectly. Doreen was great and helpful, and the hot tub was amazing. Would stay again!"

o
Ori
Shady Pine ยท 2024

More options

Exterior
Cheshire, MA

Shady Pine

Cheshire, MA

๐Ÿ›
6
bed
๐Ÿšฟ
3
bath
๐Ÿ‘ฅ
Sleeps
14
โ™จ๏ธ
Hot Tub
Exterior
Lanesborough, MA

Highland Acres

Lanesborough, MA

๐Ÿ›
6
bed
๐Ÿšฟ
3
bath
๐Ÿ‘ฅ
Sleeps
14
โ™จ๏ธ
Hot Tub
Exterior
Williamstown, MA

Eph's End

Williamstown, MA

๐Ÿ›
6
bed
๐Ÿšฟ
5
bath
๐Ÿ‘ฅ
Sleeps
21
โ™จ๏ธ
Hot Tub
ร—

Events & Weddings

What's included

Pricing

How to inquire

Final event pricing and terms confirmed per property and date.