8 homes in the Berkshires for your ideal winter getaway

Real Estate

From Great Barrington to Williamstown, we’ve got you covered.

If you’re longing to hit the slopes without crossing state lines, the Berkshires are calling.

We have curated a list of eight Berkshire County homes where you can sit back and relax with your loved ones après ski:

9253 Mountainside Drive, Hancock

$579,000

3 bedrooms, 2 full baths, 1 half bath 

1,666 square feet

Pets Unknown

Parking 2 spaces

Fee $653

⛷️1 mile from Jiminy Peak Mountain Resort in Hancock

***

37 Egremont Plain Road, Great Barrington 

$875,000

4 bedrooms, 2 full baths

3,284 square feet

1-acre lot

⛷️5.6 miles from Butternut Ski Area and Tubing Center in Great Barrington

***

33 Eleanor Road, Pittsfield

$529,000

4 bedrooms, 2 full baths

2,197 square feet 

0.29-acre lot

4.6 miles from Bousquet Mountain Ski Area in Pittsfield

***

85 E. Main St., Stockbridge

$875,000

4 bedrooms, 4 full baths

2,668 square feet

0.80-acre lot

1.7 miles from Holiday Inn Club Vacations Oak n’ Spruce Resort in South Lee

***

1554 North St., Pittsfield

$399,000

2 bedrooms, 2 full baths

1,152 square feet

0.18-acre lot

7.1 miles from  Bousquet Mountain Ski Area in Pittsfield

***

580 S. Main St., Unit 408, Lanesborough

$150,000

1 bedroom, 1 full baths

600 square feet

Pets Unknown

Parking 1 space

Fee $311 a month

8.7 miles from Jiminy Peak Mountain Resort in Hancock

***

160 Water St., Unit 209, Williamstown

$495,000

1 bedroom, 1 full bath

1,296 square feet

Pets Unknown

Parking 1 space

Fee $503 a month

13.5 miles from Jiminy Peak Mountain Resort in Hancock

***

148 Maple Ave., Unit 28, Great Barrington

$798,700

2 bedrooms, 2 full baths

1,141 square feet

Pets Unknown

Parking 1 space

Fee $375 a month

3.9 miles from Butternut Ski Area and Tubing Center