Cape Cod vs. The Berkshires

Where Should You Buy Your Massachusetts Vacation Home?]

So you’re thinking about buying a second home in Massachusetts? Excellent idea. With more people working remotely and short-term rental demand booming, a vacation home isn’t just a retreat—it’s a revenue stream.

But where should you plant your getaway roots: the breezy beaches of Cape Cod or the tranquil mountains of the Berkshires?

Let’s break it down:

Feature🐚 Cape Cod🌲 The Berkshires
VibeNautical, coastal, sunnyPeaceful, artistic, mountain air
Popular TownsChatham, Falmouth, WellfleetLenox, Stockbridge, Great Barrington
Main ActivitiesBeaches, boating, seafoodHiking, museums, music festivals
Peak SeasonSummer (Memorial Day–Labor Day)Summer + Fall foliage (June–October)
Rental IncomeHigh (up to $4,000/week)Moderate (~$2,000/week)
Typical Home Price$650K–$1.2M+$450K–$850K

Consider These Questions Before You Buy:

  1. Are you looking for summer fun or year-round peace?
    • Cape Cod shines in summer, but traffic can be intense.
    • The Berkshires are quieter, with appeal stretching into fall and winter.
  2. Will you rent it out?
    • Cape Cod homes command premium summer rents.
    • Berkshires appeal to a steady stream of artists, hikers, and seasonal visitors.
  3. Do you plan to retire there one day?
    • Cape Cod offers more medical facilities and proximity to Boston.
    • The Berkshires provide a slower pace and strong cultural life.

My Take as a Local Real Estate Agent:

  • If you want that classic beach escape and are okay with the higher price tag and seasonal crowd, Cape Cod is your best bet.
  • If you’re after something quieter, artsier, and potentially more affordable, The Berkshires might just be your dream spot.

📞 Whether you’re leaning toward the coast or the mountains, I can help you find the right property, run the numbers, and connect you with local rental management companies to maximize your return.

👉 Let’s talk strategy—schedule a 15-minute call with me today and take the first step toward your dream retreat.

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