Just 20 minutes northwest of Boston, Winchester delivers on its promise of location, location, location. You’ll get a lot of bang for your buck moving to the suburbs here, with an abundance of family-centered activities combined with many outdoor recreational spaces for cross-country skiing & trail hiking. An American town for Francophiles, Winchester has been a sister-city of Saint-German-en-Laye, a Parisian suburb, for 26 years. In the relationship, many individuals and government officials have spent sabbaticals in each city, hosted by local families. Fun fact: the original Black Horse Tavern, an important meeting place for soldiers and citizens during the American Revolution, was built in Winchester in 1724.

A small suburban town located in Middlesex County, Massachusetts
A 20 minute drive from Boston, MA
Getting Here
Take I-93 N to exit 33, and follow S Border Road to Main Street in Winchester

The Escapes

The Norman Rockwell Town of the 21st Century

Whether you are young or old, Winchester has a very navigable downtown. There are only about 30,000 residents and the town is quite compact, so you can walk, bike or drive to the center of town. Once you're there, you can do all your errands on foot. Grab your coffee at A Fuller Cup, Bagel Land, Brueggers, Starbucks or Dunks. Then hit the post office, CVS, Stop & Shop, the Farmers Market( in the summer on the Common). Going out on the town? Get a mani/pedi/facial/new hairdo at the dozens of salons in town-- we are a well groomed bunch!

Read More

Live Chat

Let Us Help You Find The Perfect Escape