Historic Gilded Age Riverfront Mansion, Pool, Tennis, Sleeps 20+, 70ac on Hudson

Built in 1885 and featured in Martha Stewart Living magazine, Midwood is one of the Hudson Valley's most storied private estates — a 12-bedroom Gilded Age mansion set on 70 acres of rolling riverfront land, 2.5 hours from New York City.
This is not a vacation rental that happens to have history. History happened here. The estate was built by a descendant of Robert R. Livingston, who helped draft the Declaration of Independence. Franklin Delano Roosevelt rode the carriage road behind the Big House while courting Eleanor before their 1905 wedding. For the past 40 years, the property has been cared for by a family of artists, educators, and community builders. Every room reflects that.
The Big House
12 bedrooms, most with private bathrooms, sleeping 20+ guests comfortably. Each room is richly furnished and full of character — original artwork, vintage furnishings, layered textures that reflect generations of creative life. No two rooms are alike.
The shared spaces are made for gathering: a formal dining room that seats 16+, a double living room perfect for group evenings or lazy afternoons by the fire, and a fully equipped kitchen with a professional-grade stove and new refrigerator. Step out onto the west-facing porch and you'll understand why families keep coming back — the Hudson stretches wide before you, the Catskill Mountains rise on the far bank, and ships sail past day and night.
The Grounds
Swimming pool tucked in the woods
Tennis court
Private waterfront and river access
Carriage road and walking trails across 70 private acres
Expansive lawn for outdoor gatherings
Parking for 14 vehicles on-site
WiFi, Nest heating, washer/dryer — everything you need to feel at home
The Location
Midwood sits in the heart of the Hudson Valley, centrally located between Hudson, Red Hook, and Rhinebeck. Two and a half hours from NYC by car; 20 minutes from Amtrak stops in Hudson and Rhinecliff. Nearby towns offer galleries, restaurants, farm stands, and markets — Rhinebeck and Hudson in particular are worth a full day each.
Midwood is a historic family estate built in 1885 and is best experienced as a lived-in country home rather than a modern luxury hotel. Guests should expect creaking floors, antique furnishings, uneven surfaces, older fixtures, and the occasional quirks that come with a property of this age and scale.
• The house is richly layered with books, artwork, family objects, and collected interiors accumulated over generations. While professionally cleaned between stays, Midwood is intentionally not a minimalist or “staged” rental experience.
• The property is home to a small community of long-term residents (“villagers”) who live in separate buildings on the estate grounds and may occasionally be seen using shared outdoor areas such as the pool, tennis court, or driveways. They are respectful of guest privacy and most guests find the arrangement unobtrusive.
• There is currently no air conditioning at Midwood. Fans are provided, and the thick historic walls generally help keep the house cooler than outdoor temperatures, but summer guests should expect a traditional old-house experience during warmer periods.
• Due to the historic nature of the home, some plumbing, lighting, and appliances may require gentler use and occasional patience.
• Midwood is ideal for family gatherings, retreats, dinners, reunions, and relaxed celebrations. It is not suitable for late-night parties, amplified outdoor music, or high-intensity event weekends.
• Wildlife is common on the property, including deer, foxes, wild turkeys, and the occasional black bear. Please supervise pets and children accordingly.
• The estate includes pools, waterfront access, uneven terrain, wooded paths, and historic structures. Guests assume responsibility for supervising children and using all amenities at their own risk.
• Professionally catered events, weddings, commercial productions, and gatherings with outside guests require advance approval and a separate agreement.