From Bethesda Magazine: How a Bethesda woman refreshed a Kent Island rental

Jenna Jacobson’s second home features nautical blues, whites and tans

By Jennifer Barger

July 20, 2026 12:20 p.m. | Updated: July 20, 2026 12:23 p.m.

Kent Island. Photo by Hometrack Real Estate.

When Bethesda real estate developer Jenna Jacobson purchased a 1995 four-bedroom, three-and-a-half-bathroom colonial in Stevensville, Maryland,last summer, she envisioned filling it with nothing but guests by transforming it into a vacation rental.

“I’ve worked in both residential and hospitality development, and I’ve been wanting to create a place that was super fun and easy for parents and kids to escape to,” she says.

The 2,932-square-foot, two-level house boasted an enviable position on 1.25 acres of waterfront property that backs out to Chews Creek, a tidal inlet on the Eastern Shore’s Kent Island. The Chesapeake Bay and a sandy beach are just two blocks away. “I fell in love with the property—the land, the water, the location,” Jacobson says. She purchased the place in July 2025 with intentions of converting it into a comfortable luxe rental for families. This is Jacobson’s first go at playing host, but her plan is to convert several homes on the Eastern Shore into short-term accommodations.

“I aimed for every detail to make family travel feel special, easy and enjoyable for both parents and kids,” Jacobson says. She and her husband, Michael Jacobson, a lawyer, bring their two sons—Cody, 4, and Carter, 7—out to stay some weekends. “The boys have been market researchers, opening boxes and testing out the child-sized furniture.”

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Jacobson is part of a larger trend that’s seen D.C. area residents wanting to own—or rent—a piece of the laid-back water-side lifestyle.

“Since the COVID-19 pandemic, many second-home buyers and investors have been attracted to coastal Maryland,” says Joanna Dalton, the Annapolis-based real estate agent who listed the Stevensville house. “I think the water, the space and how relaxing this area feels appeals to them, whether they want property for their own getaways or to play host.”

Though the structure and grounds were shipshape, Jacobson knew she wanted to give everything a breezy update. The interiors felt a tad basic: white walls in most rooms, dated oak-finish cabinets in the kitchen, and discordant terra cotta-hued walls in the great room facing Chews Creek. And she didn’t think the redbrick exterior suited the waterfront setting. Jacobson hired Beltsville, Maryland’s IMS Home Improvement to do the painting, woodwork and construction projects her vision required.

“I wanted a light and airy mood so you immediately feel like you’re on vacation,” says Jacobson, who christened her property with a seaworthy name, The Landing at Kent Island. Over the next three months “we shifted the home’s palette to reflect the coastal nature of the property—and to connect it with the stunning water views,” she says. The key to going Chesapeake chic? Redoing walls and other surfaces in beachy blues, creams and grays, and filling the rooms with serene-yet-whimsical furnishings and accents, some with a nautical bent.

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By November, she was renting the house to families, including one group that stayed over Christmas. Jacobson handles bookings via Airbnb, Vrbo and her website: landingkentisland.com. “In the beginning, I visited several times a week to do quality controlchecks and ensure everything looked great for guests,” she says.

Now she comes out a couple of times a month and employs a local caretaker, handyman and cleaning crew. “I video chat with the cleaning team after each clean so I can look over everything remotely,” Jacobson says. “Then my caretaker does a final walk-through before new guests arrive.”

Jacobson used PowerPoint to plot out the interior designs herself. “I layered in every element, testing out 50 different throw pillows or paint colors,” she says. “Then I created 3D renderings and started ordering furniture, wallpaper and accessories.” Jacobson sourced products from multiple stores and websites (Homesense, Macy’s, Maisonette, Etsy), trying to keep the style and functionality high and costs reasonable.

The exterior brick was painted in Romabio Masonry Flat in a pale white. “I thought it gave the place a statelier look,” Jacobson says. That paint “provides a more natural texture and holds up better long term.” The green shutters were redone in a driftwood-y gray (Magnolia Home’s “Sunday Stroll”) and the front door was brightened with a robin’s-egg blue (Benjamin Moore’s “Intuition”). Dinky brass-and-glass sconces flanking the front door were replaced with a pair of Sean Lavin’s jumbo “Galena” lanterns from Visual Comfort. “They’re nearly 3 feet tall,” Jacobson says. “That larger size worked better with the scale of the exterior facade.”

The seaworthy vibe flows into the interiors. In many spaces, Jacobson and her construction crew added wainscoting or moldings painted in Benjamin Moore’s creamy “Chantilly Lace.” “Architectural details and millwork add so much traditional character,” she says. The foyer was wallpapered in York Coverings’ “Annapolis Light Blue Crustacean” crab pattern.

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Toward the rear of the house, Jacobson kept the existing kitchen’s generous floor plan and nearly new white quartz countertops, but had the oak cabinets sanded and repainted in Benjamin Moore’s “Santorini Blue.” The existing chrome cabinet hardware was replaced with brushed brass pulls. Jacobson purchased small appliances (a teakettle, a waffle iron) in a pale
blue mimicking the cabinet paint. At check-in, guests find a gift bag of waffle mix and syrup near the waffle iron.

Jacobson drew on her own hospitality expertise to lean into hosting. Experts point to a few things that can help make a home
appeal to renters. Kaitlyn Collins of Easton, Maryland-based High Tide Staging & Design (which helps second-home owners prep their houses for renting) says comfortable, durable furniture and broadly appealing decor is key.

“Unlike a primary residence, you’re designing for a rotating audience, not one specific lifestyle,” Collins says. “We focus on
pieces that are comfortable, easy to maintain and able to withstand frequent turnover. Function is just as important—ample seating, durable dining surfaces and practical storage all make a big difference for short-term stays.”

Another welcoming change? A coffee bar Jacobson created by removing the doors from a small pantry adjacent to the kitchen. Her contractor assembled a Wayfair wooden cabinet and topped it with a custom butcher-block counter, mimicking the look of a built-in. The nook’s back wall was covered in a blue striped wallpaper and kitted out with a neon sign reading “but first, coffee” and floating shelves to store mugs. “The coffee bar really expanded the kitchen storage and made the whole space feel bigger,” Jacobson says.

Adjacent to the open kitchen, a dining area holds a table seating eight from Bob’s Discount Furniture paired with white wooden chairs. “Since this house sleeps so many people, I wanted to be sure everyone had a spot at the table,” Jacobson says. It’s connected to a media-free den—Jacobson calls it “the Unplug Zone”—furnished with four rope-sided chairs and a round, low table—ideal for evening cocktails or playing a board game (the house provides plenty). A print of oyster shells in dreamy blues by Annapolis artist Kim Hovell hangs over the fireplace, anchoring the room.

“You want to use a more refined, layered approach rather than leaning into obvious coastal themes,” High Tide Staging & Design’s Collins says. “Instead of overt nautical decor, incorporate subtle nods—natural textures, soft blues and greens, light
woods and organic materials. The goal is to reflect the setting without competing with it, especially when the real highlight is the surrounding water and landscape.”

Up the center staircase are four bedrooms—two with en suite bathrooms, two sharing a hall bath. The primary bedroom, which also boasts a small office space, was made over with a dramatic pale wood canopy bed positioned against a wall covered in Love vs. Design’s “Mod Herons” wallpaper in a custom blueish gray-and-white colorway. The pirate-themed kiddos’ room contains two bunk beds (sleeping four little buccaneers), a steerable ship’s wheel on the wall, and ocean-related books. A downstairs den with a pull-out sofa provides additional sleeping space.

Downstairs, the family-friendly, big-group energy continues into the spacious great room at the rear of the house. Jacobson loved the existing vaulted, wood-paneled ceiling and dazzling views of the kidney-shaped outdoor swimming pool and Chews
Creek. “It’s a beautiful room with stunning natural wood ceilings and windows on three sides,” Jacobson says. “But the walls were painted this burgundy red and the space had dated decor. I wanted it to have a wow factor.”

So Jacobson had two of the three great room walls redone in Benjamin Moore’s pale off-white “Swiss Coffee” paint and added Brewster Home Fashions’ “Mariko Blue Botanical” wallpaper on the remaining wall. She brought in a sculptural “Kayde” rubberwood and acacia dining table from Thomasville that seats 10, pairing it with wooden chairs painted—what else?—blue. A tweedy gray sectional sofa from Bob’s Discount Furniture provides lounging space for a crowd, while a kids corner with a wee French bistro table and a tiny tent appeals to pint-size beachgoers. A record player—with a stack of vintage LPs scored on Etsy—sits on a bar cart.

Just outside the great room, dips in the pool and paddles in Chews Creek await (the house comes with two kayaks and personal flotation devices). Resort-like touches—a firepit surrounded by Adirondack chairs, kid-size lounge chairs, a jungle gym—up
the appeal. There’s even a child-size metal jeep “bar” that can be set up with ice buckets for drinks or popsicles. “I just get such great feedback about gatherings around the firepit or memories of roasting marshmallows,” Jacobson says. “So many people say they plan to come back.”

–Jennifer Barger is a writer based in Washington, D.C., and the content director of Consumers’ Checkbook. Follow her on Instagram @dcjnell or subscribe to her design-focused travel newsletter, The Souvenirist, on Substack

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Originally published at Bethesdamagazine