Dog Boarding in Pittsfield, WI
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Pittsfield dog boarders
“Shanna was incredible! She took care of our boy somewhat last minute + he honestly had more fun than he would have with us :) If we’re ever in town again, we would gladly leave Zeb in Shanna’s care.”
“Cuse was well cared for and was exhausted when I got home 😁. He had a blast playing with the other dogs. Communication was great with Melissa and shared multiple pictures with me. Cuse will visit again!”
“Heather gave frequent updates and pictures to ease my mind that our dog was well taken care of and also having fun. She was great in communicating pick up and drop off and offered a lot of flexibility. Thank you Heather!!!”
“Brandy is amazing. She has watched our pup twice now! This most recent sit was a week long and she sent daily photo updates and always responds quickly. Shes a superb choice to trust your animals with.”
“Great dog sitters. Nice house with a dog door and a big yard where your dog can play. Friendly people who know how to take care of dogs. Other dogs for your dog to play with. They contacted me every day with pics of my dog having fun. And they sent him home with a toy. I’d definitely book them again.”
“Stacey was so kind and gave all the love my kitty needed for his day out the house. I really appreciate when people are so loving and kind to animals, and Stacey is just that! Definitely recommend booking with her. She was very quick to respond and gave me updates throughout the day.”
“Highly recommend! Our pup got lots of love and attention. Kristal and company made him feel right at home and kept us updated the whole time! We will definitely look to them again in the future if we need a sitter.”
“Our dog had an excellent stay! She treated him like one of the family. I also got updates every day or so, which was really nice to see. We will definitely use Mackenzie again for our dog”
“We dropped off our dog for a weekend on very short notice and Suzy was very accommodating and responsive to questions and messages. Suzy was very kind and welcoming when we arrived to drop off our puppy. She also sent us an update during our trip which was awesome. Overall, Suzy is a great sitter and we will likely rebook in the future.”
“We are so lucky to have found Denny and his family to care for Lexie! Lexie adapted so quickly and seemed to really enjoy her time at Denny's home. Denny was very good with communicating and sending pics during Lexie's stay. She looks forward to seeing him again soon! Your pet will be in good care in Denny's home! Thank you!”
“We are so grateful to have found Anu and her family to care for our Ginger. Ginger loves going there to play and visit. They have become like her second family! She's already had 3 stays and a 4th one planned. Highly recommended!”
“Shelby and her family were absolutely fantastic! They loved on our Winston and catered to his specific needs. I felt so comfortable and at ease knowing he was in a good, safe, and loving home! Highly recommend.”
“Teressa was able to watch our senior dog on short notice, she sent plenty of updates which helped relieve any worries while we were out of town. I so appreciate her making Milo feel at home away from home for the weekend!”
“Carol took amazing care of my dog, Basil, and I couldn’t be more grateful. From the moment I dropped her off, I knew she was in loving hands. When Basil was hesitant to eat, Carol went the extra mile by adding a bit of gravy to her food — such a thoughtful touch that made a big difference. Carol’s children were also incredibly sweet and gentle with Basil. Myles even told her stories, and it was clear that Basil felt right at home. She quickly bonded with their dog and settled in beautifully. Basil was allowed on the furniture and treated like a true member of the family, which made me feel so at ease. It’s not easy to leave your fur baby behind, but knowing she was so loved and well cared for made all the difference. I highly recommend Carol to anyone looking for a warm, responsible, and attentive dog sitter. We’ll definitely be booking with her again!”
“Rose took good care of my Brownie. He got to go to the park, for walks, car rides and met new friends. Brownie seemed comfortable with Rose. Rose communicated with me all week and sent pictures.”
“We were so happy to find Aryn on Rover to care for our dogs for a weekend away! She was especially patient with one of our dogs that experiences separation anxiety. We really appreciated her communication and care for our dogs!”
Loving dog boarding sitters in your neighborhood
Search Results
Shanna L.
“Shanna was incredible! She took care of our boy somewhat last minute + he honestly had more fun than he would have with us :) If we’re ever in town again, we would gladly leave Zeb in Shanna’s care.”
Melissa M.
“Cuse was well cared for and was exhausted when I got home 😁. He had a blast playing with the other dogs. Communication was great with Melissa and shared multiple pictures with me. Cuse will visit again!”
Heather S.
“Heather gave frequent updates and pictures to ease my mind that our dog was well taken care of and also having fun. She was great in communicating pick up and drop off and offered a lot of flexibility. Thank you Heather!!!”
Rebecca W.Star Sitter
“Rebecca was absolutely amazing! She communicated consistently the entire time which I appreciated. Puff seemed like he had a blast with her dogs as well. ♥️”
Bobbi T.Star Sitter
“Bobbi and her family did a phenomenal job of taking care of my dog, Archie for a 14-day stay! Every expectation was exceeded! Highly recommend!”
Brandy D.Star Sitter
“Brandy is amazing. She has watched our pup twice now! This most recent sit was a week long and she sent daily photo updates and always responds quickly. Shes a superb choice to trust your animals with.”
Holly D.Star Sitter
“Great dog sitters. Nice house with a dog door and a big yard where your dog can play. Friendly people who know how to take care of dogs. Other dogs for your dog to play with. They contacted me every day with pics of my dog having fun. And they sent him home with a toy. I’d definitely book them again.”
Stacey R.
“Stacey was so kind and gave all the love my kitty needed for his day out the house. I really appreciate when people are so loving and kind to animals, and Stacey is just that! Definitely recommend booking with her. She was very quick to respond and gave me updates throughout the day.”
Kristal K.Star Sitter
“Highly recommend! Our pup got lots of love and attention. Kristal and company made him feel right at home and kept us updated the whole time! We will definitely look to them again in the future if we need a sitter.”
Danielle M.
“Had a nice backyard for Mia to play in with a high fence. Danielle sent me a ton of pictures and had a good time with Mia. Highly recommend 5/5.”
Mackenzie M.Star Sitter
“Our dog had an excellent stay! She treated him like one of the family. I also got updates every day or so, which was really nice to see. We will definitely use Mackenzie again for our dog”
Suzy D.Star Sitter
“We dropped off our dog for a weekend on very short notice and Suzy was very accommodating and responsive to questions and messages. Suzy was very kind and welcoming when we arrived to drop off our puppy. She also sent us an update during our trip which was awesome. Overall, Suzy is a great sitter and we will likely rebook in the future.”
Denny H.Star Sitter
“We are so lucky to have found Denny and his family to care for Lexie! Lexie adapted so quickly and seemed to really enjoy her time at Denny's home. Denny was very good with communicating and sending pics during Lexie's stay. She looks forward to seeing him again soon! Your pet will be in good care in Denny's home! Thank you!”
Anuradha N.Star Sitter
“We are so grateful to have found Anu and her family to care for our Ginger. Ginger loves going there to play and visit. They have become like her second family! She's already had 3 stays and a 4th one planned. Highly recommended!”
Colleen B.Star Sitter
“Colleen was wonderful with our dog AJ. Our pup was well cared for, happy, and we got lots of updates while we were away. We can’t recommend Colleen enough!”
Shelby A.Star Sitter
“Shelby and her family were absolutely fantastic! They loved on our Winston and catered to his specific needs. I felt so comfortable and at ease knowing he was in a good, safe, and loving home! Highly recommend.”
Teressa K.
“Teressa was able to watch our senior dog on short notice, she sent plenty of updates which helped relieve any worries while we were out of town. I so appreciate her making Milo feel at home away from home for the weekend!”
Carol S.
“Carol took amazing care of my dog, Basil, and I couldn’t be more grateful. From the moment I dropped her off, I knew she was in loving hands. When Basil was hesitant to eat, Carol went the extra mile by adding a bit of gravy to her food — such a thoughtful touch that made a big difference. Carol’s children were also incredibly sweet and gentle with Basil. Myles even told her stories, and it was clear that Basil felt right at home. She quickly bonded with their dog and settled in beautifully. Basil was allowed on the furniture and treated like a true member of the family, which made me feel so at ease. It’s not easy to leave your fur baby behind, but knowing she was so loved and well cared for made all the difference. I highly recommend Carol to anyone looking for a warm, responsible, and attentive dog sitter. We’ll definitely be booking with her again!”
Rose M.
“Rose took good care of my Brownie. He got to go to the park, for walks, car rides and met new friends. Brownie seemed comfortable with Rose. Rose communicated with me all week and sent pictures.”
Aryn V.
“We were so happy to find Aryn on Rover to care for our dogs for a weekend away! She was especially patient with one of our dogs that experiences separation anxiety. We really appreciated her communication and care for our dogs!”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 152 sitters provided dog boarding in Pittsfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Pittsfield dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Pittsfield have an average of 16 years of experience. Dog boarding sitters with repeat customers have an average of 8 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Pittsfield.
Rover makes it easy to find Pittsfield dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 152 dog boarding sitters in Pittsfield on Rover, so you’re sure to find the perfect match for your dog! In Pittsfield, 88% of sitters offer daily exercise, 100% offer medication administration, and 94% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
Connect anywhere with the Rover app
