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.
Good to Know
Midwood is newly listed on VRBO, and we're offering introductory pricing to welcome our first guests through the platform. The estate has been hosting family reunions, retreats, weddings, and gatherings for decades — you'll be in very good hands.
The listed rate covers self-catered use of the house and grounds for groups of up to 20 guests. If you're planning a professionally catered event, additional fees and a separate agreement apply — reach out and we're happy to discuss. All prices shown include fees. No surprises at checkout.