Search Holiday Homes in Stockbridge

"The house and location both perfect for a girls weekend away! "

"Kind and responsive host."

"The property was centrally located for skiing, and was a comfortable stay."

"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "

"excellent communication with property manager."

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."

"My family and I had a lovely stay at Oscar’s Pond Estate! The house was clean and inviting, and provided everything we needed for a comfortable stay. The surrounding area provided beautiful views as we enjoyed the back deck and yard, complete with a hot tub and fire pit. I highly recommend the nearby Art Omi sculpture park if you stay here. It was a perfect outing for our 2 families with 4 kids ages 2 to 9. The owner was incredibly warm and responsive and provided clear and easy check-in...

"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

"House was clean and made our Thanksgiving great with it's size and amenities. "

"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"