About Us
At Waypoint House, we believe your daily adventure should start in a space that feels welcoming, comfortable, and refreshingly modern.
Every morning begins with a delicious homemade breakfast and a restful night’s sleep in our thoughtfully appointed accommodations, the perfect fuel for exploring everything our region has to offer. Looking for a hidden gem restaurant, a scenic hike, or a local winery? Just ask. We’re here to provide the personalized hospitality and insider tips that make your stay unforgettable. Best of all, you don’t have to leave your four legged family members behind. Our pet friendly bed and breakfast proudly welcomes your furry companions along for the journey. Find yourself right at home here, and let the Shenandoah Valley be your playground.
Built in 1884, Waypoint House has been a part of Berryville's history for more than 140 years
Originally constructed as the home of Miss Nannie Wilmer McGuire, the property has welcomed generations of residents and travelers while preserving much of its historic character and charm.
Over the years, the home has changed hands only a handful of times, making Rachael and Jonathan just the sixth owners in its history. Today, they are proud to build upon the property’s established legacy as a hosted bed and breakfast, continuing a long tradition of welcoming travelers while blending historic charm with modern hospitality.
The name Waypoint House reflects both the history of the property and its role within the community. Just as a waypoint serves as a point of guidance for travelers, Waypoint House has long been a place of comfort, rest, and hospitality for those passing through Berryville. It is a tradition Rachael and Jonathan are proud to continue for many years to come.
Every historic home has a story, and ours begins with Miss Nannie Wilmer McGuire
The home was built in 1884 specifically for Nannie, the daughter of Dr. William McGuire and Nancy Boyd McGuire, and she remained a beloved member of the Berryville community throughout her life.
Nannie’s family was closely connected to an important chapter of American history. She was the first cousin of Dr. Hunter Holmes McGuire, the noted physician who served as Chief Surgeon in General Stonewall Jackson’s Corps during the Civil War and famously performed the operation to amputate Jackson’s arm following the Battle of Chancellorsville. Her younger brother, William, later married Dr. Hunter McGuire’s daughter, further connecting the two families.
Although Nannie never married, she devoted much of her life to her community and was an active member of Grace Episcopal Church, where she is buried today just four blocks from Waypoint House. She also had a deep love for music, and one of the home’s most treasured artifacts still tells that story today. A portion of the original shipping crate used to deliver her piano has been carefully preserved, offering guests a tangible connection to the woman who first called this house home.
More than 140 years later, Nannie’s legacy continues to live on through the history of Waypoint House, allowing guests to experience not only a beautiful historic home, but also the remarkable story of the woman who first filled it with life.
Meet your hosts Rachael
and Jonathan Worsley
Rachael and Jonathan Worsley are the owners and innkeepers of Waypoint House Bed and Breakfast, where they bring together decades of hospitality experience, creativity, and hands on care to create a warm and personal guest experience.
For Rachael, Waypoint House represents the fulfillment of a dream more than eleven years in the making. She brings more than twenty years of experience in the hospitality industry, along with studies in culinary arts. As a Certified Food Protection Manager, she keeps her credentials current and pairs her love of food with high standards of care. She also spent seven years as a Senior Account Executive for one of Washington, D.C.’s premier catering companies, where she learned the value of thoughtful service and anticipating what guests may need before they ask.
Jonathan serves as the Commander in Chief of everything else. Whether he is helping with breakfast, maintaining the grounds, working on renovations, or keeping the property in order, he is usually in the middle of a project. His background in theatrical and special events lighting taught him to think creatively and solve problems quickly, skills that now come in handy throughout the inn. When he does slow down, you will often find him in his workshop creating traditional style leaded stained glass windows.
Together, Rachael and Jonathan believe the best stays are personal, comfortable, and easy. Whether they are sharing a favorite local recommendation, helping with plans for the day, or simply making sure guests have what they need, their goal is for every visitor to feel genuinely welcomed and cared for.
The Breakfast Experience
Each morning, guests enjoy a thoughtfully prepared plated breakfast served in our dining room. Our menu changes daily and seasonally, featuring hot entrées, fresh fruit, breakfast meats, and homemade accompaniments inspired by the season. Supporting local businesses is an important part of who we are. We’re proud to serve freshly roasted Cordial Coffee from just two blocks away and love partnering with other local businesses including Chilly Hollow Farm for fresh eggs and produce. To give you a taste of what to expect, we’ve put together a sample menu of breakfast dishes we’ve served over the years.
*We happily accommodate dietary restrictions, food allergies, and to go options whenever possible because we believe every guest deserves a breakfast they’ll remember.
*We happily accommodate dietary restrictions, food allergies, and to go options whenever possible because we believe every guest deserves a breakfast they’ll remember.
Can you accommodate food allergies or dietary restrictions?
Absolutely! We want everyone to look forward to breakfast. We are happy to accommodate a wide variety of dietary restrictions and food allergies, including vegan, vegetarian, gluten free, dairy free, and specific ingredient avoidances, with advance notice. Because we take food safety and preparation very seriously, please let us know about any dietary needs or allergies when you book your stay, or at least 24 hours before your arrival, so we can plan a delicious homemade menu just for you.
Do the owners, Rachael and Jonathan, live on the property?
Yes. We live on site in a separate, private section of the home. While we are always nearby and happy to assist you with anything you need to make your stay memorable, your privacy and comfort are our top priorities. You will have all the space you need to relax and enjoy your time in the Valley.
Are there cats at Waypoint House?
Yes. Rachael and Jonathan have three resident cats who stay in the private owners’ quarters and do not have access to guest rooms or public spaces. Guests with allergies can feel comfortable, and cat lovers are always welcome to ask for a quick hello.
Bed and Breakfast vs. Hotel vs. Airbnb: What's the difference?
When you choose a hotel or a standard short term rental, you’re usually just paying for a place to sleep. When you stay at Waypoint House, you’re choosing a curated travel experience. Here, there are no check out chores and no lackluster breakfast buffets.
Our philosophy is built on anticipating your needs before you even have to ask. From the exquisite detail work inside our historic walls to our local insider recommendations for the perfect winery or scenic hike, we take the guesswork out of your trip. You get total privacy and modern conveniences, backed by the safety and comfort of knowing your hosts are on site to handle the details. When you Wake up at Waypoint and Visit the Valley, you aren’t just lodging, you’re being taken care of.
Book Your Stay!
At Waypoint House, our goal is to provide a bed and breakfast experience like no other. Our home is historic, but we offer modern style and convenience coupled with old fashioned hospitality. We strive to anticipate our guests’ needs and exceed their expectations in every aspect, creating a stay that is both comfortable and memorable.
