Search Holiday Homes in Stockbridge

"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"

"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."

"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."

"We had a wonderful time, we’d be happy to come back again "

"Wonderful property and host very responsive."

"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."

"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"

"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "

"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!"

"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!"

"Great place and welcoming stay!"

"Very good trip overall. Great location. Just a few things needed to make it over the top!"

"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."

"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "

"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"

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

"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"

"Great property and the host was extremely responsive and helpful."