Traveler’s Retreat Room
- 2 Guests
- 1 Queen Bed
- 1 En Suite Bathroom
Settle into Waypoint House’s most spacious guest room, featuring abundant natural light and a deluxe private bathroom with a freestanding soaking tub and separate walk in shower.
Welcome to
Waypoint House
A historic Bed + Breakfast nestled in the charming town of Berryville, Virginia.
Waypoint House Bed + Breakfast
Your perfect, pet-friendly gateway to the Shenandoah Valley
Our historic B&B seamlessly blends old-world charm with every modern convenience you need. Plus, we’re ideally located, just minutes from Winchester and a little over an hour’s drive from Washington, D.C.
Accomodations
Find the perfect room for your stay
Each room at Waypoint House has its own unique character, combining historic charm with modern comforts to create a relaxing place to unwind.
Shore Room
- 2 Guests
- 1 Queen Bed
- 1 En Suite Bathroom
Relax in a peaceful beach inspired retreat with cozy accommodations, garden views, and a private en suite bathroom with a tub and shower combination.
Hearth & Home Room
- 2 Guests
- 1 Queen Bed
- 1 Private Bathroom
Settle into a warm and inviting retreat featuring three east facing windows, comfortable seating for two, and a wood burning fireplace for cozy seasonal stays.
The Breakfast Experience
At Waypoint House, breakfast isn’t just the first meal of the day—it’s an experience
Each morning, guests enjoy a plated, hot breakfast served in the main dining room. Menus change daily and seasonally, featuring thoughtfully prepared dishes made with fresh ingredients. We are proud to support local vendors, including Cordial Coffee, roasted just a few blocks away in downtown Berryville. We happily accommodate dietary restrictions and food allergies. Simply let us know your preferences during the reservation process.
Explore Berryville
Wake up at Waypoint,
Visit the Valley
Whether you want to stroll to the independent shops and restaurants of downtown Berryville or drive out to explore the wider Shenandoah Valley, Waypoint House is your ultimate starting point.
We are perfectly positioned for you to discover the region’s unique charm—from outdoor adventures and local wineries to vibrant seasonal events. Immerse yourself in history at Harpers Ferry or wander the beautiful trails at the State Arboretum of Virginia; it’s all just a short trip away.
Meet Your Hosts
Innkeepers Rachael and Jonathan Worsley are passionate about creating memorable stays
Rachael channels over two decades of professional hospitality experience into every thoughtful detail. Jonathan acts as the property’s energetic multi-tasker, handling everything from kitchen prep to immaculate groundskeeping. Always available to provide local recommendations or a helping hand, Rachael and Jonathan prioritize the guest experience above all else.
Do you allow children or pets?
Waypoint House is a pet-friendly B+B! We welcome well-behaved, house-trained animals. There is a $20 per night per pet fee and we allow a maximum of two pets per room.
Please note that animals may NOT be left unattended at the inn and must be quiet and accompanied at all times. Please be sure to review our full pet policy for additional information.
Because we are a destination for guests seeking rest and relaxation, and often those travelers have made plans for the care of their own children while they are away, we regretfully cannot accept children under the age of 10. Children who are ages 10 and older are welcome. Please call the inn prior to booking to let us know you will be traveling with your child.
What is your cancellation policy?
Because we are a small independent property, cancellations affect us significantly. Once your reservation is confirmed, the following policies apply:
Cancellations with 10+ Days’ Notice: You will receive a refund of your deposit, minus a $40 cancellation fee per room.
Cancellations with Less Than 10 Days’ Notice: The deposit taken at the time of reservation is non-refundable.
Cancellations with Less Than 72 Hours’ Notice (or No-Shows): You will be charged the full amount of the entire reservation.
Please note: We are unable to offer refunds or credits for early departures or late arrivals.
Is there free Wi-Fi and parking on site?
Yes, and both are complimentary! We offer free, high-speed, fiber-optic Wi-Fi that is accessible throughout the property including all guest rooms and our backyard seating area.
We provide four on-site parking spaces. Our designated guest spots are easily identified by white painted lines and clear signage.
Do the rooms have private bathrooms?
Yes, each of our three guest rooms feature a private bathroom. For the Hearth & Home room, your designated private bathroom is located just down the hall rather than inside the room itself—but rest assured, it belongs entirely to you during your stay.
Do you have any first-floor rooms, or ADA accessible rooms?
We love the historic charm of our 1800s home, but its age does come with architectural limitations. We do not have ground-floor guest rooms or an elevator. All accommodations are situated on the second floor and require climbing a 20-step stairway. Additionally, accessing the front door from our parking lot requires walking up a small set of brick stairs with approximately four steps.
We want every guest to have a safe and comfortable stay, so if you have any concerns about mobility or luggage assistance, please reach out to us before booking—we are always happy to help you gauge if our property will be a good fit for your stay!
What time is check-in and check-out?
Check-In: Any time after 3pm. If you plan to arrive after 7:00 PM, please call us prior to your arrival date so we can update your reservation and avoid marking your stay as a no show.
Check-Out: Before 11am
To offer you maximum flexibility on your travel day, we use a keyless, self-check-in process. You will receive an email with your individual door lock code and a link to a personalized video tour one day before you arrive. This allows you to walk right in and get settled at your own convenience. On your final day, check-out is promptly at 11:00 AM so that we can meticulously clean and refresh the inn for our next guests.
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.
