Break Away Vacation Rentals and Property Management- Established 2020
Break Away Vacation Rentals is a locally owned and operated vacation rental and property management company based in the heart of New Hampshire’s Lakes Region. We specialize in helping families, couples, and adventure-seekers find their perfect lake escape, whether it’s for a weekend, a season, or something longer.
Founded on a love for hospitality and a deep appreciation for the beauty of lake life, Break Away offers a hands-on, boutique-style experience that larger companies simply can’t match. With a growing portfolio of properties ranging from rustic cabins to luxury waterfront homes, we pride ourselves on delivering personalized service to guests and homeowners alike.
Our close-knit team lives and works right here in the Lakes Region. We’re not just managers, we’re your neighbors, your go-to guides for the best local restaurants, hidden hiking trails, and perfect paddle spots. Whether you’re booking your first stay or listing your property with us, our mission is simple: to make every stay stress-free, seamless, and unforgettable. When you Break Away with us, you’re not just booking a vacation, you’re becoming part of our lake-loving community.
Gail Archibald, Owner & Principal Broker
Gail is the powerhouse behind Break Away Vacation Rentals, launching the company in February 2020 with a vision to build something special from the ground up—and she’s done exactly that. As the Owner and Principal Broker, she keeps the wheels turning on everything from guest relations and property operations to managing software systems, employees, and homeowners. If it happens at Break Away, Gail’s got her hands on it.
A proud New Hampshire native, Gail has spent her entire career in the Lakes Region hospitality and property management scene. She and her husband managed a cottage resort on Lake Winnisquam for 17 years, followed by roles managing other local resorts and working as GM of the area’s largest rental agency. With decades of experience and a heart for both homeowners and guests, Gail brings unmatched expertise—and a whole lot of grit—to everything she does.
When she’s not juggling it all, Gail can be found boating, as a passenger on the Harley, or chasing the sunshine—especially in winter! She’s recently rediscovered her love of tap dancing and loves nothing more than spending time with her grown children in Texas and Massachusetts. Her favorite part of the job? Helping homeowners generate income while giving guests and tenants a memorable place to stay in the region she loves most.
Jessica Haines, Licensed Rental Specialist
Jessica is a Rental Specialist at Break Away, focusing on long-term rentals and helping clients find the perfect place to call home in the beautiful Lakes Region. A lifelong resident of Meredith, Jessica’s deep roots in the area give her a unique and personal connection to the charm, community, and natural beauty that make this region so special.
What Jessica loves most about her role is the chance to connect with people from all over the world who share her love for the Lakes Region. Whether guests are planning to stay for a season or settle in more permanently, she brings her local knowledge and warm, welcoming energy to every interaction.
When she’s off the clock, Jessica enjoys spending time with her fiancé Doug, her son Brycenn, and their beloved dog Maverick—often exploring the very same lakes and trails she recommends to clients. She also has a serious need for speed: you’ll often find her at New England Dragway, where her love of cars and adrenaline takes center stage. Fun fact: Jessica is a graduate of Barbizon Modeling School in Boston, adding a little extra flair to her already vibrant personality.
Megan Hollowood, Licensed Rental Specialist
Megan is a Licensed Rental Specialist with a deep-rooted passion for hospitality and helping guests feel right at home. With over 20 years of customer service experience, she began her journey in the hospitality industry in 2016 and officially stepped into the vacation rental world in 2023. In 2024, she earned her real estate license, bringing even more insight and professionalism to the Break Away Rentals team.
Originally from Southern California, Megan has lived in a few scenic corners of the country, including Iowa, Utah, Nevada, Massachusetts, and now the beautiful Lakes Region of New Hampshire, which she’s called home since 2022. She’s constantly inspired by the natural beauty of the area and loves helping guests experience everything it has to offer.
When she’s not working her magic behind the scenes or connecting with guests, Megan enjoys exploring New England with her husband and daughter, diving into a good book (or three!), and planning her next adventure. Megan brings warmth, enthusiasm, and a keen eye for detail to everything she does, making her a key player in delivering top-notch experiences for both guests and homeowners.
Rocky, Office Dog & Director of Snacks and Snuggles
Rocky is the heart and soul of the Break Away office, our beloved office dog and unofficial Director of Snacks and Snuggles. With a wagging tail and an ever-watchful eye on the treat jar, Rocky brings joy, calm, and just the right amount of chaos to the workday.
When he’s not supervising team meetings, you can find Rocky lounging in the sun, following the scent of snacks, chasing his herding ball, or offering emotional support during those extra-busy summer days. Born with an unmatched talent for boosting morale and melting hearts, Rocky reminds us daily why we love what we do—and that sometimes the best coworkers are the ones with four legs and fur.
