Overview
Fifty acres of rustic hillside sit between Crozet and Charlottesville in Ivy, and Bailey's Retreat has spread itself across them: a log cabin that was here before any of the rest, and a handful of cottages tucked into the side of Bailey Mountain with views and outdoor seating that come standard. The Baileys began sharing the estate roughly fifteen years ago, and by their own account they have hosted thousands of guests and tenants from around the world since. It reads less like a hotel and more like a working family property that decided, at some point, to open its gates.
The address is 1667 Baileys Retreat, Charlottesville, VA 22901 — Ivy, technically, on the far side of the county line from Crozet proper but well within the orbit of anyone weighing a countryside stay near town. You can reach them at (434) 960-0678 or through baileysretreat.com.
The cabin and the cottages
The centerpiece is the cabin, and it has a real story rather than a manufactured one. It was built in the 1800s as the original family homeplace, then restored and renovated for contemporary needs — the kind of place where the bones are genuinely old and the plumbing is not. It is one of the more popular short-term rentals in the state, according to the retreat, and it books through Airbnb as the C-ville Log Cabin. If a single restored log cabin on a wooded acreage is the specific thing you are after for a weekend, this is that thing.
Around it are four cottages, nestled into the mountainside and pitched at longer horizons. These are the mid-term and long-term options — available furnished or unfurnished, with multiple pricing packages sorted by lease length and how much furniture you want provided. The furnished versions are appointed for extended stays rather than overnight ones, which makes them a real answer to a real Charlottesville-area problem: where to put someone here for weeks or months. A relocation in progress, a work project with an end date, temporary housing during a build or a transition, a soft landing before a permanent move to the country — the cottages are shaped for those situations more than for tourism. A separate farmhouse, a three-bedroom, rounds out the bookable homes.
Getting around from here
The retreat also runs its own transportation arm, and this is worth knowing before you arrive rather than after. Bailey's Retreat Tour Company has been providing tours and transportation to residents and visitors since 2008. They will custom-design a tour or outing for a group and pick you up wherever you are staying — the retreat itself, a hotel, an Airbnb, an office. Wine country is the obvious application in this part of Virginia, but the pitch is broader than that: they design the outing around you and, in their words, return you safe and sound and happy. For a group that wants to spend an afternoon at wineries without anyone drawing the short straw as designated driver, having the lodging and the driver under one roof is a genuine convenience.
What's within reach
The location does a lot of quiet work. The retreat sits moments from UVA and Monticello, close to the central Virginia business and healthcare communities, and within easy reach of Shenandoah National Park — which is part of why it functions equally well for a Monticello-and-Downtown-Mall weekend and for someone in town on a months-long assignment near the hospital or the university.
Charlottesville itself is the near draw: the Downtown Mall for boutiques and cafes and gourmet food, the wineries and breweries, the restaurants. The Blue Ridge is the far one. The Appalachian Trail runs north and south within striking distance for hikers, and for anyone who wants the scenery without the climb, the Blue Ridge Parkway and Skyline Drive deliver overlook after overlook from behind the wheel. Crozet's own trailheads and vineyards sit on the same side of the mountains, a short drive west.
What Bailey's Retreat is, in the end, is a piece of countryside close enough to town to be practical — an 1800s cabin for the weekend crowd, four cottages for the people who need a season rather than a night, and a driver on call for the afternoons in between. Browse the full list at baileysretreat.com/properties, or call (434) 960-0678 to sort out which of the homes fits the length of your stay.
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Frequently asked questions
Where is Bailey's Retreat Cabins and Guesthouses?
Bailey's Retreat Cabins and Guesthouses is located at 1667 Baileys Retreat, Charlottesville, VA 22901, USA, in Crozet, Virginia.
How do I contact Bailey's Retreat Cabins and Guesthouses?
You can call (434) 960-0678 or visit https://www.baileysretreat.com/. Hours and current information are most reliable directly from the business.
What kind of business is Bailey's Retreat Cabins and Guesthouses?
Bailey's Retreat Cabins and Guesthouses is categorized as lodging in our Crozet directory. See the description and quick facts above for what makes this listing distinctive.
Sources: baileysretreat.com