Pen y Bryn - 5BR Blue Ridge Luxury Retreat with Pool, Library & Game Room

A Note Before You Book
Thank you for your interest in Pen y Bryn! We want to be upfront: the house is still awaiting a handful of finishing details, which we expect to have fully complete by the end of October 2026, and you may notice a lack of photos right now. The home is fully functional and comfortable to stay in now — nothing about your stay or the core experience will be affected — but a few final touches are still being wrapped up. We'll keep this listing updated as those finishing touches are completed, and we're happy to answer any specific questions before you book.

The Story Behind the Name: Pen y Bryn
The name Pen y Bryn came with the house — it was given by the original owners and means "top of the hill" in Welsh, a fitting name for a home perched exactly where it is, looking out over the Blue Ridge. When our family purchased the property, we chose to keep the name, both because it so perfectly describes the setting and because our own family has Welsh roots as well. It felt right to preserve a piece of the home's history while adding our own chapter to it — and we hope Pen y Bryn feels like exactly that for your group too: a true top-of-the-hill retreat.

Your Private Mountaintop Escape
Perched at the top of a hill with sweeping, uninterrupted views of the Blue Ridge Mountains, this estate was made for the trips that matter — the annual girls' getaway, the bachelorette weekend everyone still talks about, the multi-generational family vacation. Total privacy, total luxury, and space for everyone to spread out, together.
Step outside to your own resort: a stunning plaster pool paired with a detached 8-person spa, framed by mountain views on every side. Whether you're planning a champagne-toast bachelorette weekend, a reunion where old friends can finally slow down and talk, or a family trip with cousins splashing in the pool while the grown-ups relax nearby, this backyard delivers.

Built for Gathering
Inside, the house is designed around bringing people together without anyone feeling on top of each other:
- Great Room with soaring wood truss ceiling beams — the heart of the home, and the best seat for those mountain views
- Custom-built white oak library — a quiet, gorgeous spot for morning coffee, a book club session, or a quiet toast before the party starts
- Chef's kitchen + outdoor kitchen, both flowing seamlessly to a dining room that comfortably seats 20+ — no one eats at a separate table here
- Cabana bar with glass garage doors that open completely to the pool deck, so the party never has a hard edge between indoors and out
- Game room with retro arcade games and a 100" projector screen — game night, movie night, or the low-key hangout space after a big day
- Sun room for the quieter moments — reading, journaling, or just soaking up the light

Rest Easy, However Your Group Sleeps
Five bedrooms are designed to work for every kind of trip:
Four bedrooms with private en-suite baths — ideal for couples, girlfriends who want their own space, or family units keeping some separation
A hall bath with a tub — perfect for bathing little ones
A custom-built bunk room with privacy curtains — genuinely fun for kids, but comfortable enough that adults request it too. Great for a bachelorette party that wants one room to be the "sleepover" room, or for cousins who want to bunk together on a family trip

Unbeatable Location
Minutes from Wintergreen Resort for skiing, snowboarding, and mountain activities year-round
On the doorstep of the Route 151 corridor, home to some of Virginia's best-loved wineries and breweries — a built-in day of tastings without ever needing a long drive
Tucked away for total privacy, yet close enough to everything to make planning easy
Whether you're reconnecting with your closest friends, celebrating a bride-to-be in style, or making memories with the whole family, this Blue Ridge hilltop retreat gives your group the space, privacy, and luxury to make it unforgettable.

Exterior Monitoring Devices:
The property is equipped with two exterior cameras that monitor the driveway access for the safety of our guests and protection of our property. The house also has 3 video doorbells that also record audio, as well as a 4th facing the parking/driveway on the entry to the detached garage. The detached garage is not available to guests.