Top Vacation or Second Home Destinations For Bostonians

Top Vacation or Second Home Destinations For Bostonians


We’ve all read the articles about the vacation/second home boom happening right now courtesy of the ongoing pandemic. With the anticipation of a second wave and possible stricter lockdowns, those Bostonians fortunate enough are seizing the day and investing in a vacation or second home. Here are some top destination choices.

Kennebunkport, ME


Located just an hour and a half outside of Boston on Maine’s southern coast, Kennebunkport offers respite from city life complete with quaint shops, art galleries, restaurants (re: lobster and seafood), and of course, the ocean. The Bush’s have a compound here and Martha Stewart is a frequent visitor as well.

Stowe, VT


Best known for its top-notch skiing, Stowe is reminiscent of a quaint resort village you’d find in Aspen or the Swiss Alps. There’s also plenty to do in the off-season with easy access to nearby lakes such as the Waterbury Reservoir and Lake Elmore, plenty of trails for hiking, biking, local art galleries, breweries, restaurants, and much more. Bonus: it’s also super close to the Ben & Jerry’s factory.

The Berkshires, MA


Located in the western part of the state, the Berkshires are home to an impressive number of cultural and historical sights such as Tanglewood (the Boston Symphony’s summer home), the Mass Museum of Contemporary Art (MoCA), and the Norman Rockwell Museum. They’re also known for their hiking and water sports. This is an ideal vacation/second home choice for those looking for culture and adventure.

Lake Winnipesaukee, NH


A mere 2-hour drive from Boston will transport you into a water-lovers playground. Lake Winnipesaukee is the largest lake in New England. There’s boating, fishing, water sports, and a town to fit everyone’s needs from the resort-feel of Wolfeboro to old-fashioned Meredith. It’s also ~40 minutes to the mountains for skiing.

Cape Cod, MA


Can you even have an article about vacation/second homes near New England without mentioning the Cape? If a peaceful, coastal setting is what you’re after, then one of the Cape’s 23 towns is sure to fit your needs.


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