Places to stay in Stockbridge

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!

Their place was perfect for a couples weekend getaway. It was very clean, convenient, and we loved our stay there. The overall location and the town itself were perfect for our romantic ski weekend plans. Andrew and Susanne were very kind and inviting and were excellent hosts!

U have stayed here many times and it is always a gret experience

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!

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.

Patricia's place is a great hideaway with easy access to some of the areas highlights, including Shelburne Falls and Mass MOCA (within 40 minutes). The space is thoughtfully decorated, the kitchen is extremely well-stocked and her warm welcome of our dog was much appreciated. With or without a canine companion, this is a terrific, quiet spot. Highly recommend.

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.

To be gifted the experience of staying at this lovely home on Lillie Pond is something to behold. I booked a few days here with hopes of exploring the nearby attractions, various trails and the gorgeous lands around. Instead, I spent countless hours on the deck, looking out at the pond and observing the busy springtime activities of the beavers, geese, ducks and more. Inside the record player and piano were a welcome addition. The kitchen was well stocked for any cooking needs. The evening brought the peepers out to serenade, as the stars were on brilliant display from both the deck and the hot tub. There is great attention to detail and care in all of the spaces of Tiffany and Scott's home. There were wonderful welcome gifts as well- thank you! I had a few questions during my stay and the hosts were super helpful, kind and responsive. I would love to come back! Thank you for sharing your beautiful home!