Oscar's Pond Estate

⭐️⭐️⭐️⭐️⭐️ Oscar’s Pond Estate in Old Chatham, NY is a true Hudson Valley retreat. The property sits on a peaceful private pond surrounded by rolling hills and beautiful Columbia County countryside. The outdoor amenities - the deck, hot tub, and seating areas - are fabulous. The home is spotless, spacious, and perfect for a relaxing Upstate New York getaway. It’s just minutes from Chatham, Kinderhook, and Hudson, with great local restaurants and scenic hiking nearby. If you’re looking for a tranquil stay, in any season, this classic Hudson Valley house - Oscar’s Pond Estate - is for you.

We had an absolutely wonderful stay at Oscar’s Pond Estate in Old Chatham! The house is beautifully maintained, spotless, and full of cozy touches that made us feel right at home. Nestled in a peaceful and scenic part of Columbia County, it’s the perfect escape from the hustle and bustle. We especially loved the spacious yard, well-equipped kitchen, and relaxing mornings on the porch with a cup of coffee. The hosts were gracious and responsive, making the whole experience seamless. Can’t recommend this place highly enough—already looking forward to our next visit!

This house in Old Chatham, NY is an absolute winter wonderland. We stayed during a snowy weekend…a magical scenery blanketed in snow as if from a postcard. The home was warm, beautifully decorated, a mix of rustic charm with modern comfort. After a day of exploring local trails and cozying up in the large living room, we ended our nights in the outdoor jacuzzi under the stars. It was peaceful, private, and exactly what we needed to unwind. We’re already thinking about a return trip next winter.

One of the most peaceful and relaxing stays I’ve had in a long time. Oscar’s Pond Estate is a hidden gem. The house itself is super clean and cozy, and the jacuzzi was a perfect touch—especially at night under the stars. I spent a lot of time just sitting on the porch taking in the view, which was honestly incredible. You can tell the owners put a lot of thought into the space. Great for a weekend getaway or just to unwind for a few days. Highly recommend!

I spent a weekend at Oscar’s Pond Estate in Old Chatham NY and it was absolutely magical. The property is tucked among rolling hills near a charming farm, with stunning views and total tranquility. The home is cozy, beautifully decorated, and full of character. Mornings by the pond with coffee and quiet were a dream, and evenings watching the sunset with wine were unforgettable. It’s the perfect escape to unwind and reconnect with nature. I left feeling completely refreshed—can’t wait to go back!