Patricia Azze and her husband, Jazz, had never been to the Berkshires when they decided to buy a house there. The couple live in Miami full-time with their dog, Roo, but they had dreams of running a hospitality business. “We like to say we arrived there via not romantic or cold-hard research,” Patricia says with a laugh. The home simply met all their criteria.

The pair hoped to own a rental property in a place that had seasonal appeal (that way it wouldn’t be sitting empty half the year) and was within three-ish driving hours from at least one major city—the Berkshires is practically in the middle of New York City and Boston. Other boxes that needed ticking? Recreational marijuana had to be legalized in the area and there should be a cool, open-minded community that guests could tap into (a natural wine bar didn’t hurt). 

“I had all these bizarre things that I wanted, because it would allow us to grow into a boutique hospitality brand,” explains Patricia (that hospitality brand is now called Warm Welcome Stays). It just so happened that an 1886 farmhouse in the frequently searched town of Great Barrington met all of these requirements—and it had the potential inside, too (after some TLC). Ahead, Patricia shares how they applied all the things they’d learned from staying in previous rentals (the good and the bad) to their own retreat.


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Give Every Type of Guest a Hangout Spot

Given the pair was rental shopping during a pandemic (they tackled the project this past summer), they wanted a house with enough space so people could enjoy spreading out on their vacation. “This home had a lot of ‘chill zone’ potential,” says Patricia. In other words, there were enough rooms and bedrooms (five total, but they turned one into an office) so guests wouldn’t be on top of one another. “And you wouldn’t have to be precious about keeping your voice down if someone wants to watch a movie in one space and another wants to sit and have a cocktail elsewhere,” she adds. (The sustainable cork flooring throughout the home also helps dampen sound, plus it’s antimicrobial.) The kitchen, though, become more of an active, cozy communal room with bistro tables and a built-in bench where visitors can keep the group’s designated chef company or enjoy coffee in the morning while overlooking the wetlands. 

Consider Regional Differences

Their big advice for others looking to invest in a rental in an area they’re unfamiliar with: Ask people you trust who are from there lots of questions, like who they’d recommend as a real-estate agent and contractor. For the Azzes, it was things like: Do we need wool blankets? How does a wood-burning fireplace work? Is this a normal heating system? “We’re tropical creatures, so all of a sudden we had to learn a lot about the New England cold and what to do,” says Patricia. “Central AC is an absolute must in Miami, but it’s not a big deal in the Berkshires.” 

An Office Is Crucial

Carving out areas where multiple guests could work remotely was a top priority. “We went to a wedding where the house was full of people but the Wi-Fi was weak and there weren’t good, private work zones, so it was kind of a headache for those working and those who weren’t,” recalls Patricia. So the couple designed three desk zones, two inside of bedrooms, and one private office (ideal for long-term guests who want a “designated work area,” as Airbnb calls it). “Especially if you have kids, you want to be able to close the door for privacy when conferencing,” she adds.

No One Gets a Tiny Bed

“I’ve been on lots of trips that come down to rock, paper, scissors for the ‘bad room’ (aka the twin bed or sofa),” says Patricia. Nobody wants the short end of the stick just because they’re the youngest or the single one. So she made a point to go with all queen-size beds (and one king-size bed). One of the rooms has two queen beds that share a nightstand, so you still have that sleepover-hotel feel but everyone has room to stretch out. And it’s okay if the bed takes up a decent amount of space. “You don’t need a lot of other furnishings in a rental, just a place to sleep and a place to put your clothes,” she notes.


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Have Fun With Your Paint Picks

Even though the couple’s home in Miami is nearly all white, they decided to have fun with paint for the rental. “You maybe wouldn’t live with all this color, but it’s fun for a vacation,” says Patricia. Her brother showed up on site with a friend two days after the couple arrived at the house to begin the cosmetic renovations and got to work on the paint. “He was ready, so we had to decide super-fast on the colors,” she recalls. Her gut instinct led her to a blue kitchen, a violet bathroom, and a “Kermit the Frog” green bedroom. “Everyone thought I was crazy for that. Now it’s the favorite room in the house,” she says. 

Visit this ultra-bookable Massachusetts getaway here.