74 Hilltop Rd

Welcome to 1000 Oaks, a distinctive Rhinebeck country retreat.
Set on 6.8 acres, this summer rental offers a 3,200+ square-foot main house and a heated 14' x 26' gunite pool, all surrounded by the quiet beauty of the Hudson Valley landscape.
Like many exceptional homes shaped by a clear point of view, 1000 Oaks reflects the spirit of wabi-sabi, the time-honored Japanese philosophy that finds beauty in imperfection, simplicity, and harmony with the natural world. Here, the landscaping remains intentionally natural, wildflowers are welcomed and cultivated, and materials such as wood, fieldstone, and brick are thoughtfully woven throughout the property. Inside and out, a soft palette of earthy, low-contrast tones creates an atmosphere that is calm, grounded, and quietly beautiful.
The home offers several especially appealing features. The family room includes an attached full bath, making it ideal for visiting guests. On the second floor of the tower, an office provides two dedicated workspaces, while the tower’s third floor serves as a workout space, with walls of windows overlooking the property. In summer, once the trees are fully leafed out, the setting becomes especially secluded and serene. The heated pool is, of course, one of the season’s great pleasures.
Despite its sense of privacy and retreat, 1000 Oaks is conveniently located just 6 miles from the center of Rhinebeck Village, 6 miles from the Taconic State Parkway, and only a short distance from the Rhinebeck Performing Arts Center.
Whether your summer in Rhinebeck or the Hudson Valley is devoted to rest, work, culture, or simply a change of rhythm, 1000 Oaks offers a setting with a strong sense of place. Its beauty is not formal or showy. It lies, instead, in the quiet coherence of the house, the land, and the life they make possible together. Coming soon - available for showings on April 8th, 2026.