Doggy Day Care in Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
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Top rated Winchester doggy day care sitters
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Janette and her family, including their dog Luna, are so wonderful to our dog, Lenny. She is so kind and communicative! Lenny loves spending time with them and going for walks in their beautiful neighborhood. Thank you so much for taking such great care of our dog!”
“Fantastic puppy sitter!! Jasper loves going to play at Carol's and comes home exhausted. I love knowing he's well looked after, happy, and safe. Great communication and pictures. Thank you so much!!”
About: Since coming to college, I’ve started volunteering at the Humane Society where I’ve been day-fostering! Love dog sitting/walking for friends and neighbors. Would be more than happy to take care of your pups :) I’m a college Senior with a light course load this semester and plenty of free time, especially on weekends. My schedule is normally pretty consistent with classes from 12-2pm. Outside of those hours I’m very flexible! I have no pets at my home and have the energy to entertain your pet (no matter how energetic they are). I’m a safety-first kind of person and big on communicating any areas of uncertainty!
“Was so thankful when I last minute needed a puppy sitter and I found Surendra! She sent me videos and updates of our puppy and was great at communicating. Would highly recommend!”
About: Master's degree in animal care and welfare. Former vet tech for dogs and cats at an E.R. I also have an Animal Science degree and have cared for horses and other animals. I work from home some days, part-time, and always have walk breaks. I go for long walks and will join with doggy playmates if your dog is able. Will also walk small dogs in carriages for fresh air. Have fenced in yard for small and medium size dogs. I have a fenced in yard and one Bichon rescue dog who is older, and friendly with other dogs. I was a former vet tech and have much cat and dog health care skills.
“We needed daycare for Halo last minute and Oana & Oliver totally came through! Oana was responsive, professional, took the time to understand Halo's quirks and make sure Halo would be a good fit with the other dogs they were watching, and sent lots of wonderful photos! It was such a relief to feel comfortable that Halo was in great hands!”
“Another great stretch of daycare days with Likun and EL! He races to her house every morning which tells me he loves going! I can go to work knowing he’s in good hands. Thank you again!”
“Yesika has been amazing for doug. He is always so excited to see her, and is always exhausted when he comes home. Yesika will take doug on walks during day care and gives him an opportunity to play with other dogs. It's been great! I can't recommend Yesika enough!”
“Lexi took great care of Emmy during her daycare visit! She was very attentive to Emmy’s needs and made sure she felt comfortable and happy throughout the day. We appreciated all of the updates Lexi sent us during the visit!”
“A truly 5 star experience. Cameron was easy to communicate with and work with. Just off vibe alone I knew my dog was in good hands when he was picked up. Throughout the day I was consistently updated with photos and videos of my dog out and about. I highly highly recommend Cameron to anyone in need of a dog-sitter. Next time I’m in Boston I will 100% be reaching out to him first. Finn will miss Cameron and Rosie a ton!!! 5 stars!!”
“My pup had the best time ever in the yard, chilling in the house, and befriending Betsy’s sweet dog. I even got a photo during the day. :-) Looking forward to her next stay!”
“I have trusted Elizabeth and Neil with Rocko for the past several years and I couldn’t be happier. Rocko is a little shy around people and other dogs, but this family is like an extension of my own and he thrives when he is there. I receive lots of communication throughout the day so I know he is well taken care of. I am very lucky to have found Elizabeth and Neil!”
“Elizabeth and Rodrigo genuinely love Fitzgerald. Their home is loving and they are kind, communicative, and considerate dog lovers. We love visiting them cause Fitzgerald always wags his tail extra hard during drop offs, and comes home happy as can be. Anyone looking for a loving pair to watch their pup would be lucky to have them say yes!”
“Belinda was amazing with Juno and helped out while I was at work for a work trip! Juno had a great time and it was amazing knowing Juno was in great care! Thank you so much!”
“Samantha is amazing ! She is kind, communicative, and personable. It’s obvious she is an animal lover. She watched my dog Teddy for the day and he was happy and relaxed when I picked him up. Highly recommend !”
“Luci and her family were absolutely incredible for our pup! From the moment I reached out, she was incredibly responsive, professional, and accommodating. During her time with them, she was treated like family! Luci sent regular updates, including adorable pictures and videos, which made me feel so at ease. This was my first time leaving my pup alone and she was so happy every day she was there. I highly recommend!”
“Ben and his family took great care of Zelda and were very accommodating of our busy schedule. She came home happy and well exercised from playing with their pups all day. We will definitely book with Ben again!”
“Ying is really thoughtful person and takes care of my little puppy really well. My puppy enjoys playing with Ying and at the end of the day, a tired (and happy) puppy got a deep sleep and rest. Would definitely recommend her and will come to her again!!”
“Cheuck was so great with my dog Annie! I left my dog with Cheuck during the day while I was at work. He shared pictures and kept me updated regularly! I highly recommend Cheuck.”
Over 47 pet parents in Winchester have booked doggy day care
Winchester dog parents share their Rover experiences
Unfortunately, one of my dogs has cancer and I have a week of early morning trainings for work. (530a drop offs- Yikes!). Yesika is still willing to take her every day, work with the energy that she has that day, and offs care across the day (additional small meals, medication for nausea,etc). So glad that I have this resource.
Janette and her family, including their dog Luna, are so wonderful to our dog, Lenny. She is so kind and communicative! Lenny loves spending time with them and going for walks in their beautiful neighborhood. Thank you so much for taking such great care of our dog!
Sophie had a great day with Andrew! She had a few nature walks that I can never give her. She loved her day away from home. Andrew is excellent to work with and incredibly professional. He was consistently quick to respond and sent lots of pictures of their day together. Andrew had Sophie this summer for a long weekend and Sophie returned home happy as could be! It's as though she was with family. Thanks, Andrew, for making her days so enjoyable!
Brianna has taken such good care of Oliver at a really hard time for him. He is so happy to see her and her home is such warm and cozy for my dog. She communicates perfectly to let me relax after I drop him. You can tell Brianna really loves the dogs she cares for.
I recently moved to MA from out of state with my male pup, and connected with Kayla for daycare service. Kayla is experienced in providing care for pets. During my pup’s stay, she was accommodating and took such great care of my pup. She even gave him 2 doggie chew sticks, and he was so excited to take those home with him! ☺️ 🥹 Kayla is the best!
Olivia & Robin were stellar dog sitters and kept me posted on Rosie's first stay with photos and updates throughout the day, which put my mind at ease. They gave her lots of love and attention, making her feel right at home. She was very tired and happy when I picked her up, which is always a great sign. I will definitely book with Olivia again!
Popular requests near you
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The median cost per day for doggy day care in Winchester is $50
Why Choose Rover?
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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.
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Sitters in Winchester average 3 repeat doggy day care clients
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 Winchester on Rover as of Jun 2026 was about $50 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 Jun 2026, 2,752 sitters provided doggy day care in Winchester. 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, 85% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 16 years of experience. 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 Winchester.
Winchester 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 Winchester 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 2,752 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 91% of sitters offer daily exercise, 95% offer medication administration, and 88% 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 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.
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