Friends often make the best collaborators. So, when Melanie and Pliny Reynolds, East End residents and business owners, saw that the compound around the Portland Observatory on Munjoy Hill was up for sale, they tapped their friendships to snag the property and transform the historic buildings.

The couple, who at the time needed a larger space for their growing family, fantasized about turning one of the buildings into a guesthouse and living in the other. They proposed the guesthouse idea to their long-time friends Whitney and Jon Lendzion, who were as intrigued by the location as they were and agreed that the time was ripe to bring a distinctive accommodation to the hill.

The four friends make an ideal quartet for starting a business: Whitney is an interior designer, Jon is a contractor, Pliny is an architectural designer, and Melanie has experience in branding and hospitality. “We all brought something separate to the table,” says Melanie. “And we have a lot of friends in the trades industries locally, so we knew we had all the key players who could help us put it together in a special way.”

First developed by local entrepreneur Captain Lemuel Moody in the early 1800s, the compound included a marine signal tower (now the Portland Observatory, the oldest tower of its type in the United States), a house, and a dance hall and bowling alley, where townspeople and shipping industry travelers alike gathered to carouse. Moody’s granddaughter Elizabeth lived in the house where the Reynoldses now reside, and at one point rented out rooms for overnight guests. “What’s really neat about it for me is that these two properties are joined again for the first time in a long time,” says Melanie. “Reconnecting them and creating this space for guests to enjoy in the same way that people did a hundred years ago, it’s kind of a rebirth, but modernized.”

The name Best Bower, which Jon came up with, has several meanings: it’s the forward anchor on a ship, the card that ranks above the others in a particular hand, and it’s also another word for arbor. The idea of a hidden, unassuming space especially resonated with the group, as the modern iteration of the property started with the courtyard garden, which had become overgrown from years of neglect. “A sloped side yard shouldered by both the Observatory and a mature oak tree provided a natural opportunity for an enclosed terraced garden with communal seating,” says Whitney, who worked on the design. Whitney also did the gardening and landscaping alongside Jon, while Cape Landscapes built the stone walls and laid the brickwork.

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Inside, the Best Bower’s six rooms are bright with natural light but also notably private. Four of the rooms have exterior entrances off the courtyard, and the remaining two rooms, which are accessed from the street, have interior entrances on separate floors. “It was important to us to make guests feel like their room belongs to them,” says

Whitney. Much like an Airbnb rental, Best Bower, which opened on Memorial Day of this year, is for the most part a self-service place, complete with a shared kitchenette that includes a full-size refrigerator and a compact convection oven big enough to, say, heat up a premade lasagna from Rosemont Market and Bakery up the street. There are also add-on food packages that Melanie sources from local purveyors, such as a cheese and charcuterie board featuring picks from the Cheese Shop of Portland. “Once people are here they can reach out to me as much or as little as they want,” explains Melanie.

Because the team needed to fit six guest rooms into a relatively small footprint, unique rooms emerged. The room at the end of the courtyard, for example, has a particularly high ceiling, inspiring the team to add a coffered wooden design. Whitney’s brother, Wylie Wirth of Fine Furniture Solutions, used reclaimed white oak to create both the ceiling and a paneled sliding door for the room dubbed the Library.

The decor for the other rooms evolved in the same way, starting with architectural features and fanning out from there. Friends from the firm John Sparre helped to build wooden lofts for the next two rooms (Loft East and Loft West), which were narrow and tall and needed, in Whitney’s words, “large brushstrokes that were materials-driven.”

Both the last room on the courtyard (the Courtyard Queen) and the first room on the ground floor as entered from the street (the Congress Queen) have more standard volumes. “We had been stockpiling giant red oak logs from around southern Maine for the last 20 years,” says Whitney, “and we finally got to use them for built-in closets and dry bars.” Executed by Andrew Boshe of Green Tree Carpentry and Wylie Wirth, the red oak gave these rooms the punch they needed.

The sixth room, which is upstairs and off the street, has a sloped ceiling, creating the perfect opportunity for skylight views of the Observatory (in fact, three of the rooms have skylights). “The skylights frame the Observatory in a really unexpected way that you wouldn’t see anywhere else,” says Melanie. More red oak paneling, slab countertops, and quarter-sawn cabinetry by Joe Seremeth from WoodLab give the room, which is called the Crow’s Nest, a boat-like feel. “In each case, the rooms and their built details evolved in concert with the trades-person or craftsperson working on them,” says Whitney. “The Best Bower is just as much theirs as it is ours.”

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