Dog Boarding in Pittsfield

Brooke was easy to communicate with and she took good care of Allie during her stay, getting her outside for walks and playing fetch. Thanks again Brooke!

I'm delighted to share my outstanding experience with Jess as a dog boarder for Winslow. Her attentive care and the reassuring environment she provided made me feel completely at ease leaving my dog in her hands. The ultimate proof of her exceptional service is that Winslow returned home with evident happiness, a clear indication of the positive and loving atmosphere Jess creates for her furry guests. I highly recommend Jess for her top-notch dog boarding services.

I would highly recommend her! She treated my Goldie like a princess. I went away for two days and i received multiple updates with photos. She also gave me a gift of pastries which was i credibly sweet. Goldie was very happy and I will definitely send Goldie there again.

Excellent sitter, Walter came back exhausted. Daily pictures and videos of hikes with her pack and other adventures. Would definitely use again and highly recommend to others.

Mary and Todd took wonderful care of my dog Edie! Sent photos throughout here stay of their adventures and put me at ease that she was in very good hands!! Thank you and hope you are available the next time she needs a place to stay!! Best, April

Kona had a fabulous time! This was our first time using rover and we were very happy with Jonathan and how great he was with our fur baby! We greatly appreciate the flexibility and ability to book last minute! Thank you :-)

Teresa kindly arranged a meet and greet before our dog’s multi day stay, was super proactive and responsive with communication, and sent great picture and video updates throughout. And best of all, our dog had a blast playing with the other dogs. Excellent experience all around, thank you!

Jennifer is amazing, so glad we found her! Lovely home and fun yard for the doggies to play. We loved getting all the updates and pics even throughout a quick weekend stay. It’s clear she loves dogs and is very attentive and kept them entertained. We loved that she was happy to keep up their training while she had them, and learned their commands, even with 2 dogs with 2 different “languages”! Such a relief to know our dogs have a lovely place to stay when we travel and are happy, safe and having fun.

John and his wife are the best! I’m beyond thankful we found these two to put my mind at ease when we go away! Thank you for always for taking such good care of Rocky. He loves spending time with Dolly and all of you!

Deanne was amazing and so attentive. I appreciate you so much! Bleu loves her. My kitten felt so safe. I felt so safe. Thank you for being so informative and thank you for just making us feel so safe that meant a lot to me

Our dog Max had a great time with Peter and Monique. They were kind and took him for walks and offered plenty of lap time to keep him happy while we were gone.

Jayla was great she provided consistent updates on Dusty and it seems like he had a great time! Also, the drop off and pick up went really smooth.

Ericca took wonderful care of our dog. She provided daily updates with how he was doing, which put us at ease while we were away. We would happily use her again!

Franny is a very thoughtful and caring sitter. I trust not only that my 13 year old Maltese will be well cared but also that she will have a great time. Will always check with Franny first when needing a sitter.

It was so great to leave our dog with Sylva and Mark! They took such good care of her, it was great to feel like I didn't need to worry about the dog while we were gone. Will certainly reach out the next time we need a dog sitter!

Cheyenne was a great host for Mugi and on very short notice. She took great care of our pup while we were away for the weekend. Would definitely recommend!