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Adventures await at Lazy Bear Oaks!
Let the serenity of nature soothe your soul and awaken your passion to explore.

Lazy Bear Oaks is your own 14-acre sanctuary with year-round Blue Ridge Mountain vistas. Set beside pristine wildlife lands, it’s a cozy-luxury retreat wrapped in nature. Watch the sky melt into color from the western-facing balcony or enjoy morning coffee on the screened porch as a gentle breeze moves through the trees. Fire up the grill, then gather around the natural stone firepit for s’mores under a star-filled sky. Follow softly lit stepping stones to the spacious 636 sq. ft. deck, where outdoor dining, lounge seating, and a 5-person hot tub invite you to unwind with sweeping mountain views.

Rustic charm meets modern luxury in this turn-of-the-century cabin. Redwood siding, a patinaed copper roof, and a stacked fieldstone fireplace showcase timeless craftsmanship. Inside, post-and-beam construction and heated pine floors are complemented by carefully selected antiques, hand-painted artwork, and authentic taxidermy, creating a warm, character-filled retreat.

Nestled between Greene and Madison Counties in a peaceful Virginia holler surrounded by mountains and streams. About two hours from Richmond and Washington, D.C., and 24 miles from Charlottesville–Albemarle Airport. Close to Shenandoah National Park, wineries, breweries, antique shops, fishing, hiking, horseback riding, skiing, Rapidan WMA, and more. Located in Virginia Wine Country on the edge of the Monticello AVA, just 11 miles from award-winning Early Mountain Vineyards.
Escape to Lazy Bear Oaks, a peaceful retreat nestled in the foothills of the Blue Ridge Mountains. This 2-minute video tour highlights the inviting interior rooms, warm and comfortable living spaces, and stunning aerial drone footage of the property surrounded by vibrant fall colors. Video taken on October 30, 2025.
Explore the natural beauty of Lazy Bear Oaks through stunning footage captured on our game cameras. From deer and foxes to raccoons and wild turkeys, this video highlights the incredible wildlife that roams freely on the property. Perfect for nature lovers, future visitors, or anyone looking to experience the serenity and biodiversity of this unique retreat.
Video of the property in November 2019. The property was originally named Tall Oaks Hill after the large oaks behind the cabin. In April of 2020 the property was purchased and renamed to Lazy Bear Oaks.
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