The Berkshires: An Up and Coming Destination for Tourists and Investors in the Boston Aea

  • The MerGo Team
  • 03/4/21

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When Boston residents want to escape the city, there is one place that immediately comes to mind: The Berkshires. Over the past few years, the Berkshires have become an increasingly popular destination for those in the Greater Boston Area looking to explore the more rural areas of Massachusetts.

With this increase in popularity, many people are also becoming interested in acquiring a second home and turning it into a passive investment through websites like Airbnb and VRBO. So let’s take a look at why the Berkshires are exploding in popularity and how everyday people are using this time to turn their second homes into income-generating businesses. 

Berkshires: The go-to getaway for Boston residents

The Berkshires have always been a prime getaway destination for Boston residents looking to get out of the city, but over the past year, the COVID-19 pandemic has accelerated this dramatically. With lockdown rules limiting interstate travel, the Berkshires has become one of few places that Boston residents can “get away to” while staying properly quarantined. Just a few hours outside of the city, it is now the go-to destination for a weekend getaway.

It’s no surprise! Small towns like Great Barrington, Stockbridge, Pittsfield, Lenox, and Sheffield are premier destinations for tourists year round. In the warmer months, these areas have some of the best hiking trails and swimming holes in Massachusetts. In colder months, there are a number of alpine ski resorts and plenty of opportunities for snowshoeing, cross-country skiing, snowmobiling, and other winter activities. In recent years, the food scene in the Berkshires has also improved, with restaurants catering to city-dwellers looking to get away while experiencing the same quality of food they’re used to in the city.

To accelerate things even further, many city dwellers are now realizing they can essentially work from anywhere with an internet connection. Taking a two-week working vacation is now possible for many of Boston’s office workers, and the Berkshires is an ideal location.

The booming vacation rental market

With this influx of people to the Berkshires, there has been an overwhelming demand for lodging. Hotels are few and far between in the Berkshires, and most people looking to escape the busy city aren’t interested in staying at a hotel in the first place. They want somewhere they can call home for the weekend—a cabin in the middle of the woods or a cozy one bedroom home in a small town. 

Just take a look at the numbers: Between 2019 and 2020, internet searches for the Berkshires increased by 30%. In the summer of 2020, an Airbnb spokesperson was quoted as saying, “As guests search for cottages or pet-friendly retreats with plenty of outdoor activities nearby to continue safely social distancing, listings in the Berkshires are specifically popular among families, as listings meet their new, emerging needs for increased cleanliness, privacy and control over their travel experience and environment.” Weeklong rentals are becoming more common, and pet-friendly destinations with WiFi and kitchens are more sought after than ever. 

The result of all of this commotion is that many people are realizing they can turn their second home into an income-generating property, while others are looking to buy a second home with the interest of turning it into a profit center while also using it for their own vacations.

Making the decision to buy and monetize a second home 

Making the decision to buy a second home, either for personal use or as an income generating property, can be an exhausting and complex process. It might sound like a fun side project, but the reality is that the process of finding the right home, completing updates and renovations, making sure that it is marketed to the right audience, pricing, and keeping track of guests can be tiring and exhausting.

While the idea of owning a second home may seem cumbersome and overwhelming, monetizing a second home, when done correctly, can be both personally and financially rewarding. This is where we are seeing a shift in the market, where individuals who may have been scared of owning a second home are now able to not only purchase their dream home, but also monetize it and ultimately have an additional source of revenue. Websites such as Airbnb and VRBO have become the norm for people when booking vacations and getaways, making the vacation rental market even more accessible and enticing.

Now, more than ever before, individuals are buying second homes, in specific vacation destinations, with the intention of listing them as vacation rentals. For anyone considering this path, you should understand your options when it comes to managing it. If you’ve never managed a vacation rental before, doing things like calculating optimal nightly rates and marketing your home can be challenging and confusing.

Finding your management solution

Ultimately, there are three ways you can go about monetizing a vacation rental. You can manage it yourself, you can partner with a management property management company to split up the responsibilities, or you can utilize a full-service property management company that will take care of everything.

We fall into the latter category. As a full-service property management company, we take all the guesswork out of buying and monetizing a second home, with a focus specifically on the Berkshires. We manage all aspects of running a vacation home from marketing and pricing to booking to guest communication and any on-site services. And for those that don’t currently have a second home to monetize, we assist in finding and purchasing the right Berkshires home for your needs.

We understand that some owners want to manage the property themselves or they may want someone to handle one aspect of the process, like booking or marketing. But regardless, we think it’s important to understand all of the options out there. If you’re interested in learning more about how we can help you make your dream of a second home not only a reality but an income-generating investment, just click here for your free proposal. We’d be happy to discuss your goals and show you how we can help you achieve them. 

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Lucas has been in the real estate business for nearly 10 years now, and he is totally crushing it. He constantly brings an incredible energy to every meeting & has such expansive knowledge on anything from rentals to residential to commercial.

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