These unique vacation rentals – from a mid-century A-frame cabin to a cozy riverside retreat – offer rich history and thoughtfully curated spaces
By Brooke Spach
Chatham County attracts thousands of tourists and out-of-town visitors during the summer months. With an abundance of wedding venues, arts festivals, retirement facilities and nearby health care hubs, there are plenty of reasons folks are flocking to Chatham for overnight stays. Check out these three historical homes-turned-Airbnbs for an immersive, authentic getaway filled with thoughtful touches and ample amenities.
Mid-Century Sanctuary
This trio of A-frame cabins off of Manns Chapel Road is somewhat of a local landmark, and the property is characterized by a colorful past. During the late 1960s, UNC sophomore Robert Roskind purchased 10 acres surrounding a small lake in Pittsboro for $1,000. He and his friends finished building the first, leftmost cabin in just 16 days, laying the foundation for a commune that would become the epicenter of the local counterculture movement for the next decade.
The cabins’ charming facades and rural location enticed Heather Smith and Dan Smith to purchase the three A-frames after they went on the market a few years ago. The couple and their young children had relocated from West Point in 2018 and settled into a Briar Chapel home while they searched for available land to build on.
“Every time that we drove down this road, I’d say, ‘Oh my gosh, Dan, look at them,’” Heather says. “‘They’re a time capsule from the 1960s, and I’ve never seen an A-frame. If I could have them I would love to restore them.’ He was like, ‘Look away,’” she jokes.
Heather had some experience renovating their former New York home for Airbnb and was eager to take on another fixerupper. After she underwent emergency brain surgery in May 2021, Dan could see that a project would help her through recovery. They closed the following February and got straight to work bringing the middle cabin back to life (the two flanking A-frames have been home to longterm renters for several years.)
“I realized it was becoming a very therapeutic process for me to not only restore and heal this house, but at the same time it was restoring me,” Heather says. “It was helping me heal.” Encouraging relaxation and restoration was her goal for the space, which she largely furnished from local stores like Steel Roots.
The cabin had not been touched since it was built more than 50 years ago, so all of the plumbing, electrical and appliances received an update. Catwalk structures along the front of the cabin and connecting to the upstairs loft were removed to allow in more natural light and take full advantage of the A-frame’s high ceiling. The floor plan was also adjusted to show off the lakeside view from the front door, which meant moving the bathroom and rotating the original spiral staircase.
“We’re a pretty good team in that I have some technical background and experience, and Heather has talent for it, love of it, vision and spunk,” Dan says. They took on most of the projects themselves and strived to preserve the home’s character where possible. Heather opted to keep the original walls and flooring in the front of the cabin, which feature subtle relics of its past, like BB gun holes and discoloration from the wood-burning stove.
“There’s something magical about realizing the house itself is the experience,” she says. “It’s not just a place for people to stay and sleep. This house and its roots here in Chatham County, the fact that it is such an iconic location and people always want to know the story, it really is magical being here.”
Out back, Dan and Heather reconstructed a deck overlooking the water that’s perfect for outdoor gatherings. Between the cabin and lake is a grassy gully imprinted by travelers on the “Old State Road” wagon trail, serving as a further reminder of the rich history surrounding the getaway. The lake is a great spot for fishing and private lounging on warm sunny days, and the couple hopes to add a dock, paddle boats and more water activities in the future.
“You’re so close to all these main destination points to drive to, whether it be Pittsboro, Jordan Lake or Chapel Hill,” Heather says. “Then you go on the back deck, and you’re watching ducks and hearing a rooster crow, and you feel a million miles away.” To book, search for “Amazing A-Frame Cabin on 2-acre Pond” on Airbnb.
Haw River Haven
This cozy and colorful home by the Haw River is one you just can’t pass up. That’s how owners Anna Blackshaw and Tim McKee felt ahead of their move back to California in 2013, prompting them to turn their family home into a rental property. They fell in love with the people and culture of Bynum during their seven years in North Carolina, so after a few years of renting to longterm tenants, they were eager to resume enjoying their updated gem of a house.
“It allowed us to actually take better care of this 100-year-old home, and it also meant that we could come back and stay in it,” Anna says. “Those first couple of years that we rented the house out, we never stepped foot into it, even when we would come [back] to visit. So, this really allowed us to feel like we were still part of the community.”
Steps away from the Bynum Bridge, the 1920s home was originally two mill houses that were joined together in the ‘90s. The couple created a house guide which details the history of these original mill houses. With the support of their neighbors and community, Anna and Tim tore out and upgraded the entire kitchen, repainted each room and sourced eclectic furnishings from thrift stores all over Chatham and beyond.
Works from local artists are proudly displayed throughout the house, like a painting of Bynum General Store by Virgil Johnson; illustrations by Emma Skurnick; a mosaic tile floor by Erick Davis, which depicts the iconic river and bridge; and more. They also provide each guest with a jar of Fiddlehead Farm homemade jam as a welcome gift.
“It was really important that the house got to reflect this beautiful area that we called home for so long; to this day, I think we both consider North Carolina to be like a home for us,” Anna says.
Frequent Airbnb vacationers themselves, Tim and Anna know that character and authenticity make for the best experience in a home away from home. “We want [guests] to have the feeling of the local ecosystem,” Anna says. They strived to channel that throughout the property with touches like a Clyde Jones critter in the front yard and ensuring the outside areas were well equipped for front (or back) porch sittin’, a staple of the laid-back community’s way of life. The house guide is also filled with ideas for how to spend your stay the Bynum way.
“There are places where Airbnbs can be extractive within communities and not have a positive impact,” Anna says. “To that end, we try to be mindful about not only supporting our local artists, but also shepherding our guests toward local businesses, toward places in Pittsboro where they can spend their tourist dollars. We try to ensure that our presence there, providing a place for people to sleep and spend their holidays, is also benefiting the community that we got so much from.”
Anna feels that opening their home to hundreds of guests over the years has created a positive cycle by sharing the wealth of all they love about the town, and says the most rewarding part of the hosting experience is having guests come back for multiple stays.
“It’s a peaceful, serene oasis that is also part of a vibrant community,” Tim says. “It’s located in a very accessible place for all that the Triangle has to offer. … And, increasingly, I think Chatham and Bynum are kind of on the map. North Carolina is increasingly seen as a dynamic place by the rest of the U.S., so we also have some people who just really want to check this area out.” You can check out this Haw River haven by searching “A Gem of a House by the River near Chapel Hill” on Airbnb.
Rustic Retreat
“The expression ‘Hotsy-Totsy’ is just an old-timey way to say, ‘everything is right in the world,’” Jane Sacco writes of her Airbnb listing’s name. “That’s exactly how you’ll feel out here.”
Jane, her husband, Justin Sacco, and their now-14-year-old son, Sam Sacco, relocated from Virginia to Durham five years ago. Upon settling in and exploring the surrounding communities, they realized their ultimate goal was to plant roots in a more rural and secluded area. When the owner of this Civil War era farmhouse and its seven acres in Pittsboro was ready to sell, a Realtor friend alerted Jane of this “match made in heaven,” as she puts it.
“A place like this doesn’t come along all that often, so we wanted to make a move while we could,” she says. “We bought it with the understanding that we wouldn’t be able to live in it right away, so we would do short term rentals until we could make that decision to move. That’s where the idea for turning it into The Hotsy Totsy and designing it in such a way that it would be a fun vacation place kind of came about.”
Justin and Jane bought the place in March 2022 and spent the next eight months giving it a facelift. From March to October, Jane was out on the property from 4 a.m. to 8 p.m., doing what she calls “handy Jane stuff.” Maintaining the integrity of the house was top priority, so they made few major changes to the property – the biggest project was adding the home’s first indoor plumbing system and bathrooms. The couple transformed the outdoor bath house into the “Honky Tonk Bar,” a private pub and guest-favorite spot suited for enjoying a summertime cocktail and playing a round of cards.
“Every stick of furniture in this house was purchased from either a thrift store or Facebook marketplace or something like that,” Jane says. “For me, that was the really fun part of this project. It’s much less expensive, you get to meet so many different people and everything has a story.” She says sourcing each item was like a full-time job, and she had a regular route between shops in the Triangle, which included Little Boho Valley and the Chatham Habitat for Humanity ReStore.
“I never believe in fighting with what you’re working with in terms of aesthetics,” Jane says. “I think things tend to work best when everything’s in harmony. … [The decor is] old, primitive style, like the kind of thing that might have been in this house in the 1860s. I’m not a purist in that way, but that’s what inspired me.”
In the ‘80s and ‘90s, the farmhouse was home to a group of young women who jokingly called it the “home for wayward girls,” so Jane infused the decor with a fun, feminine vibe in their honor. “A lot of the way that I’ve tailored this [house] is toward honoring the past and just keeping this as a nice place for girls’ weekends, girls’ getaways, that sort of thing. I’ve also been trying to connect with people in the community to come and do special things to cater to our guests who are typically just groups of women trying to get away from their daily grind for a few days.” Jane is currently putting together a directory of resources for services like private chefs, mixology classes, flower arranging workshops, on-site massages and more.
Though you could enjoy an entire stay without ever leaving the property (Jane keeps a fully stocked dry pantry), there’s plenty to do on its large acreage and beyond, like playing horseshoes, roasting s’mores over the fire pit or going for a hike on the nearby Haw River trail system. Whether you’re planning a bachelorette weekend or looking for a family getaway, The Hotsy Totsy is the perfect place to disconnect and unwind. Book your stay here or check it out on Instagram.
