Doggy Day Care in Pittsfield
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Pittsfield doggy day care sitters
“Kevin watched our pug for two days while we attended the Quechee Balloon Festival. He was incredibly flexible with our plans and let us stay out much longer than originally planned. Our pup had a good time, evidenced by the 2nd day when we dropped him off and he ran right to Kevin! The other dogs were a bit noisy and inquisitive but settled right down so it wasn’t a problem. Kevin sent a few photos and video which we much appreciated. If we were in the area again, I wouldn’t hesitate to leave our dog with Kevin once again.”


“Sam & Thomas took excellent care of our dogs. They kept us updated with lovely photos and detailed information, which made us feel very comfortable and reassured. I believe our dogs had a wonderful time playing with their dogs, as they were happily exhausted and slept almost the entire time after coming home. Highly recommend their service!”


“Tom, Ember, and pack were great as always! We have been sending Callie a few times a week now for about a month and she comes home happy and tired every time. Callie and Ember have become best friends and will continue to send Callie to Tom’s as often as possible! The best!”



“Gwynn was great with our dog, Friday! She successfully administered her medication as needed and sent us plenty of pictures and videos during her stay. It was clear at the end of her stay that Friday was well cared for and very comfortable with Gwynn. We will absolutely be bringing her back as needed in the future!”


“We could not have imagine a better place for Cooper to hang out while we ski. Bean welcomed him right away, and Sara kept us updated all day. I don’t think Cooper really wanted to leave. Great yard. We’ll be back!”


“Alyssa is above and beyond my expectation! We don’t live near the area so we were worried about leaving them in an unfamiliar area however she conducted very thorough communications with me beforehand and made sure that we get updates regularly throughout our dog’s day care session. I highly recommend her! She also has the cutest golden retriever who is super friendly with dogs! :) i’ll definitely get back to her when we have another trip around the area.”


“Katherine did an amazing job watching our two dogs for daycare while we were on vacation. She kept in constant communication, sent adorable videos of the dogs playing and was very accommodating. I would definitely recommend Katherine and would use her again!”


About: I have 100 acres of land for your pet to run on a long lead!! Exercise is included with playtime fun!! Provide bath time too I am retired and have 100% free time to provide to your Pet!! Mon thru Sunday, any time!! Playtime , bath time and exercise !! I will be adding a fence to my yard and have a dog already! Your furry friend can socialize and be safe in Fenced yard!!

“Lorrie was fantastic! Jiminy had a great time and I he really loved her immediately! It was wonderful to have time to take a college tour and not worry about him. Definitely would use her again!”


“We left our dog with Jaimi while skiing for the day at Okemo and it went great. Our dog was a little nervous to go in, but Jaimi sent tons of photos of her relaxed and happy so we knew she was having a good time and being well cared for. Our dog came out happy at the end of the day!”


“Zach is incredible!! A true dog whisperer. I have left my 4 month old puppy, Goose, with Zach a few times and he takes such wonderful care of him. My pup is a little nervous around people and other dogs but seems to absolutely thrive with Zach and Alfie. I received frequent updates, pictures and videos which made me feel so at ease. I’m so grateful for the care and affection that he gives Goose! Looking forward to more visits in the future! 🐶💕”


“Where to begin? Everything was amazing from start to finish. It’s the most comforting feeling to have someone you love (our pup) being left in safe hands. Kasey truly loves what she does and absolutely loves taking care of our little furry ones. It truly shows. We most definitely will be back since we frequent Vermont bi-annually. Thank you for everything. HIGHLY RECOMMEND!!!”


“Grace was great! Fast communication and super friendly. My dog was instantly comfortable around her, and I appreciated the pictures I got during her stay with Grace. My dog was definitely tired when I picked her up after a day with Grace!”


About: I work remotely for an international development organization based in DC. My schedule is flexible, leaving me plenty of time to spend outdoors with some new furry friends! I have always loved taking care of dogs and come from a large, dog-owning family. I have extensive experience dog walking and sitting both small and large breeds, from Cavalier King Charles Spaniels to Labs to Bernese Mountain Dogs! I currently own a 4 year old white shepherd named Storm who loves to walk and play with other dogs. I am open to taking our pups on walks together, on trail hikes, or to the dog park. Available for daily walks, drop in visits, and dog sitting. I look forward to meeting you! Also open to discussing boarding in our home, pending meet and greet with my dog Storm. I work remotely from home, so I am flexible when taking care of dogs. Happy to work with you on a recurring schedule, or for one-time walks/visits! I work remotely full-time from home and my schedule is flexible. I take my dog, Storm, out for short (less than 30 min) and longer walks (over 1 hour) 2-3 times a day. We also enjoy using nearby trails, as well as the trails on our property. I currently live in a farmhouse in Royalton. There is no fenced in area, but we have trails on our property for dogs to walk (on leash) or run (depending on your comfort and their recall).

About: Growing up, I have never been without a pet to come home to. I truly believe dogs have the ability to alter someone’s life, and thus deserve the best care! I can assure you I will treat your pets with utmost care and love. I ran my own pet sitting business in high school, and am very comfortable with new dogs (and cats)! I am currently an M1 at Dartmouth med school. My schedule is quite flexible, just reach out for specific quests about your pet sitting needs. I live in a house with 5 other medical students. However, I am only willing to care for smaller dogs in my home. I am happy to stay with your dog for multiple hours in the day in your home!

About: I have owned and taken care of dogs for my entire life. Currently, I own a small 9lb rescue, who is 11 yrs old. In the past, I have owned medium and large dogs as well, including beagles, labs, retrievers. I have professionally and personally walked and fed dogs for neighbors and friends, our furry ones are the very best!! I am a self-employed yoga instructor, with a flexible schedule. With this flexibility, I can accommodate most days and times, both weekdays and weekends. I am organized, punctual, reliable, trustworthy, and communicative. I really enjoy walking every day and it's always better with a dog! My dog, Bodhi, fetches sticks in our backyard and stills plays like a puppy, even at 11yrs old! I take him hiking regularly, as well as to the surrounding parks, which are numerous and all within walking distance from where I live.
Loving doggy day care in your neighborhood
Search Results
Kevin & Inez W.Star Sitter

“Kevin watched our pug for two days while we attended the Quechee Balloon Festival. He was incredibly flexible with our plans and let us stay out much longer than originally planned. Our pup had a good time, evidenced by the 2nd day when we dropped him off and he ran right to Kevin! The other dogs were a bit noisy and inquisitive but settled right down so it wasn’t a problem. Kevin sent a few photos and video which we much appreciated. If we were in the area again, I wouldn’t hesitate to leave our dog with Kevin once again.”


Sam & Thomas L.
Star Sitter


“Sam & Thomas took excellent care of our dogs. They kept us updated with lovely photos and detailed information, which made us feel very comfortable and reassured. I believe our dogs had a wonderful time playing with their dogs, as they were happily exhausted and slept almost the entire time after coming home. Highly recommend their service!”


Tom D.


“Tom, Ember, and pack were great as always! We have been sending Callie a few times a week now for about a month and she comes home happy and tired every time. Callie and Ember have become best friends and will continue to send Callie to Tom’s as often as possible! The best!”




Gwynn Z.Star Sitter

“Gwynn was great with our dog, Friday! She successfully administered her medication as needed and sent us plenty of pictures and videos during her stay. It was clear at the end of her stay that Friday was well cared for and very comfortable with Gwynn. We will absolutely be bringing her back as needed in the future!”


Sarah & Ben A.

“We could not have imagine a better place for Cooper to hang out while we ski. Bean welcomed him right away, and Sara kept us updated all day. I don’t think Cooper really wanted to leave. Great yard. We’ll be back!”


Alyssa B.Star Sitter

“Alyssa is above and beyond my expectation! We don’t live near the area so we were worried about leaving them in an unfamiliar area however she conducted very thorough communications with me beforehand and made sure that we get updates regularly throughout our dog’s day care session. I highly recommend her! She also has the cutest golden retriever who is super friendly with dogs! :) i’ll definitely get back to her when we have another trip around the area.”


Sean D.Star Sitter

“Sean and his wonderful family are so kind. My dog loves to visit with them and their dogs! I feel very comfortable that my girl is well loved when I’m absent.”


Katherine C.

“Katherine did an amazing job watching our two dogs for daycare while we were on vacation. She kept in constant communication, sent adorable videos of the dogs playing and was very accommodating. I would definitely recommend Katherine and would use her again!”


Nancy H.
About: I have 100 acres of land for your pet to run on a long lead!! Exercise is included with playtime fun!! Provide bath time too I am retired and have 100% free time to provide to your Pet!! Mon thru Sunday, any time!! Playtime , bath time and exercise !! I will be adding a fence to my yard and have a dog already! Your furry friend can socialize and be safe in Fenced yard!!


Lorrie L.Star Sitter

“Lorrie was fantastic! Jiminy had a great time and I he really loved her immediately! It was wonderful to have time to take a college tour and not worry about him. Definitely would use her again!”


Jaimi L.

“We left our dog with Jaimi while skiing for the day at Okemo and it went great. Our dog was a little nervous to go in, but Jaimi sent tons of photos of her relaxed and happy so we knew she was having a good time and being well cared for. Our dog came out happy at the end of the day!”


Abbey G.

“Abbey was great! She was flexible and accommodating of our schedule. She sent many photos of our dog having a wonderful time.”


Zachary B.


“Zach is incredible!! A true dog whisperer. I have left my 4 month old puppy, Goose, with Zach a few times and he takes such wonderful care of him. My pup is a little nervous around people and other dogs but seems to absolutely thrive with Zach and Alfie. I received frequent updates, pictures and videos which made me feel so at ease. I’m so grateful for the care and affection that he gives Goose! Looking forward to more visits in the future! 🐶💕”


Kasey B.

“Where to begin? Everything was amazing from start to finish. It’s the most comforting feeling to have someone you love (our pup) being left in safe hands. Kasey truly loves what she does and absolutely loves taking care of our little furry ones. It truly shows. We most definitely will be back since we frequent Vermont bi-annually. Thank you for everything. HIGHLY RECOMMEND!!!”


Grace M.

“Grace was great! Fast communication and super friendly. My dog was instantly comfortable around her, and I appreciated the pictures I got during her stay with Grace. My dog was definitely tired when I picked her up after a day with Grace!”


Laura R.

“Laura is hands down the best dog walker I have ever had. JJ's favorite part of the day is walk time with Laura! She not only is amazing with JJ and other dogs - you can tell she is a dog lover - but she also is responsible, punctual, and attentive to JJ's needs. I know her schedule is pretty full, but if you can, try to get Laura for your Portland dog walking needs, your dog will thank you. 4 out of 4 paws!!”


Kennedy W.
“My dogs are obsessed with Kennedy . She has taken care of them on and off for the last 2years. Very dependable and caring .Highly recommend.”


Laura P.
“Oh my gosh ! I feel like not only me but my dog has won the lottery . Laura is so great with my dog . She is always upbeat, kind and always on time . My dog get so so excited when she shows up at the door . Austin and I are very happy clients 🐕☺️”
How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. 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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Doggy Day Care FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Pittsfield on Rover as of Aug 2025 was about $45 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Aug 2025, 21 sitters provided doggy day care in Pittsfield. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care 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, 88% of Pittsfield sitters offering doggy day care respond in under an hour.
Sitters offering doggy day care with repeat customers have an average of 3 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.
Pittsfield doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Pittsfield sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
There are 21 sitters offering doggy day care in Pittsfield on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care 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 doggy day care 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
