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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Loving doggy day care in your neighborhood
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1. Joshua & Kristen B.
“Very knowledgeable and patient taking care of my fur baby.”
2. Alexsys T.
“Granite had the best day ever with Alexsys. 30 min after I dropped him off she sent me a photo of a very happy dog sitting in her lap. Alexsys was so great with communication. She sent many photos and let me know how he was doing during this entire stay. We will definitely book with Alexsys again.”
3. Gabby T.
“Gabby has taken care of our dogs for over 2 years now and she is responsible, caring and hard working. My dogs love her so much and when they are with Gabby I rest assured that they will be in the best hands possible.”
4. Carrie Lynn A.
“Carrie Lynn is a great sitter. I am so thankful that I could leave my guys with her knowing that they were safe and having a great day. I highly recommend Carrie Lynn to anyone who is looking for someone to care for their pups.”
5. Shaghayegh H.
“First time meeting with Shaghayegh today. My furbaby was very happy with her at first sight. Location was spot on from my home. I couldn’t have asked for a better sitter for Coco and we are looking forward to Shaghayegh again this weekend. Definitely a repeat furmom!”
6. Yzabella V.
“Yzabella is a wonderful person and crazy dog lover. She is incredibly responsible when it comes to caring for dogs, she is experienced with administering medication when needed. She sends pictures and videos everyday to assure the owner and make it less stressful. I highly recommend Yzabella if you’re looking for someone to watch your furbaby!”
7. Angela M.
“Angela was so communicative and sweet with our Ollie.”
8. Haejin & Herscel L.
About: I’ve been lucky to spend the past 6 years caring for both dogs 🐶 and cats 🐱 of all ages. I’ve looked after pets at every stage of life — from 2-week-old kittens needing bottle-feeding to senior dogs and cats who required medication and gentle support. I do my best to understand each pet’s unique personality and needs, and I care for them with patience, kindness, and genuine love ❤️ I’m available for daily care from 6am to 6pm, and I also offer overnight or weekly boarding depending on your needs. If you have a special schedule in mind, feel free to reach out. I’ll do my best to make it work for you and your pet. I live in a quiet and spacious home with my husband and four sweet pets. We have three gentle cats 🐱 and one senior dog 🐶 who has been part of our family for over a decade. Pets who stay with us can move freely around the main floor and relax in a cozy upstairs room made just for them. There are soft beds, toys, and even a little cat wall they can climb and explore. Our neighborhood is peaceful and safe, with two small parks nearby where we can enjoy slow, sniff-filled walks or just spend time in the fresh air together 🐾 Whether your pet is outgoing or shy, full of energy or in their golden years, I always do my best to help them feel safe, comfortable, and truly cared for, just like home.
9. Walter G.
“I have been taking my puppy to stay here during the day while I'm at work. Walter and his family are truly wonderful with my puppy. Very flexible with pickup time, easy to communicate with. I have total peace of mind when I bring her here. I know she is getting lots of attention, care, and this kind of petsitter is a rare find. Highly recommend 👌 👍 👏 🙌”
10. Emily K.
“Emily does a wonderful job taking care of our German Shepard mix! She communicates well, is very flexible and accomodating and takes great care of Titus! I definitely recommend her services and will be booking with her again.”
11. Chelsea W.
“Chelsea did an amazing job watching my 4 crazy dogs. She came to my home and took very good care of them. I will absolutely use her again in the future. I highly recommend her to anyone looking for someone they can trust fully.”
12. Thomas C.
“Thomas and his dog Henry were incredibly loving and hospitable with Naima. Naima was very happy going and seemed very happy when we picked her up. Thomas took her on long walks, so she was fully taken care of all day.”
13. Kathleen C.
“Katie and Tino are huge lifesavers. If your pup is like your child, they will happily accommodate your needs. My dog looks forward to her Tuesday visits so much that if she misses a week or is unable to go, she will sulk for the rest of the day. My pup knows good people when she meets them right away. Sometimes I think she like Tino more than me :D”
14. Stefany P.
About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
15. Chelsea A.
“Chelsea did a great job watching Theo for us! We appreciate it.”
16. Crystal K.
About: My family calls me the dog whisperer. I have over twenty years of experience caring, watching, and owning all types of different breeds, sizes, and temperaments. My husband and I work from home and have two dogs ourselves. Typical millennial, but they are our furr-children. Everyday we have multiple potty breaks and play time outside. I feed my dogs twice a day and they are my entire world. My schedule revolves around them. All dogs are welcome and are part of the family. They can sit on the furniture and sleep in our bed. We have a dog ramp for the dogs to get on the couch. We have 10 acres with a big yard and lots of exercise. We have dog toy baskets on all floors of the house. We treat all pets like family!
17. Curtis & Stacy P.
“Curtis and Stacey were great as always!”
18. Haleigh H.
“Haleigh was great! She was easy to communicate with and she took great care of our little guy. Bodhi sure seemed to have fantastic time hanging out with Haleigh and her dog! Will definitely be using her again.”
19. Elise B.
“The boys were very interested in staying with Elise! They had a good time exploring the house and yard. When we came to pick them up, they were excited to see us, but not panicked and eager to leave. Considering they aren't used to being left with strangers, that's a great thing to see!”
20. Amanda K.
“Our doggo loved spending the day with Amanda this week! Amanda was great to work with and sent us lots of cute photos of him. I highly recommend Amanda for your dog sitting needs!”
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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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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 2025 was about $32 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 2025, 143 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, 91% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 20 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 143 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 94% 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 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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