5 Best Places in Massachusetts For A Couple To Live On Only Social Security

3. Pittsfield

Insider Monkey Score: 52

IM Cost of Living Index: 103

Average Rent (2-bedroom): $1,262

Median Home Price: $308,000

Livability: 74

Taking the third spot on our list of best places in Massachusetts for a couple to live on only Social Security is Pittsfield, the largest city and the county seat of Berkshire County. This charming city is best suited for active retirees who don’t want a dull day in their life. From skiing in the Bousquet Mountain to hiking in October Mountain State Park and visiting the Colonial Theatre, there is something to suit every taste.