Places to stay in Pine Plains

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

Great space, great location.

Theresa’s beautiful Norman Rockwell studio was so much better than I could have imagined! She was so thoughtful from start to finish with clear and easy communication about everything. Parking was very easy and you will clearly have a space right behind the building. The large picture window in the middle of the living room with a Christmas tree in the center was so lovely and heart warming! Very quiet yet steps from shopping and restaurants (the best breakfast in town can be had at Main Street Cafe downstairs!) I would highly recommend this charming apartment for anyone wanting a charming experience in Stockbridge. 10 out of 10!

The house is extremely comfortable. The open living area is cozy but large with high ceilings and a tv area, dining area and stools at the kitchen bar. We did not feel on top of each other. The gas fireplace is so nice in the winter and gives off heat as well as creates ambiance. The bedrooms are great with very comfortable mattresses and nice linens. Overall adorable cabin in the Catskills right off of 28 so you can easily get to other areas like skiing and dining. We would definitely come back!

Sally responded to questions right away. She was really attentive - making sure snow was cleared and ice salted so that we could leave early in the morning after a big snow storm. The place was really conveniently located 15 minutes from ski Butternut. And it was immaculately clean and so cozy. It was a really nice stay.

Jay's home is easy to arrive at and make a home away from home in minutes. It was clean, inviting and quiet! We enjoyed the quick ride to the ski slopes and the walk to Phoenicia's antique mall. The home is well-stocked and made cooking a meal at home no problem. Jay answered our questions within moments and made the stay relaxed and truly a get-away. We highly recommend his delightful home.

The space was great! It was big enough for two and decorated very nicely. The space had everything you needed, including some toiletries and misc items (iron, tea kettle, etc) which made the stay even better. Thank you!!

We had a great time staying in this beautiful and comfortable space. It had everything we could hope for and was perfectly clean. The air felt and smelled fresh as we walked in the door. It was spacious and well appointed with extras like condiments, games and puzzles. There was a dog gate and potty bags in case we brought our pets. We didn’t bring ours this time but might in the future because we definitely want to stay here again. There were plenty of clean linens and the shampoo, conditioner and body wash were great. The coffee was delicious and there was tea too. We didn’t use the air fryer, but it was nice to have that and the gas stove in case we wanted to cook. Thank you for a great stay!

Lockwood Lodge is a beautiful and peaceful place in a perfect location. Our families loved watching the snow come down from the big windows, the view is spectacular. Our kids loved the vintage video game consoles, the grownups loved the records and games/puzzles, and we all felt right at home in the lovely house. It was a perfect spot to hunker down in the snow storm. Jeremy was incredibly responsive and thoughtful and did much to make sure our stay was perfect. We hope to visit again in the summer to take advantage of the pool, which must be really special against the backdrop of that view.