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
“I’m so grateful to have found Kristin!! I’ve been bringing my boy to her for a few days a week for daycare for the pst two weeks and he has so much fun with her and his other friends! He comes home happy and tired, so I know he’s being well taken care of. I highly highly recommend her to anyone that needs any sort of service for their babies!!”

“Alvin goes to Beth’s 4-5 days a week. It’s been a few rough weeks for Alvin. He had surgery 10/1 and had a cone/collar for 12 days. She was great with keeping him from scratching but still be playful. He learned how to scoop the ball with the cone! We absolutely love the care he receives with Beth and her family!”

“Holy Smokes! Jeanne was so sweet and so kind to our new puppy. We are road tripping as a family and took our kids to Six Flags. Chip got to hang out with this lovely lady! She sent the best pictures and was very responsive. Highly recommend!”

“Elisabeth is fantastic! Our pup has been to several Rovers (we are full time RV’ers) and she is one we would definitely go back to and recommend. Our pup, who is typically very shy at first, warmed up right away. He was treated with play time, a walk, a bone to munch on, and attention. Elisabeth was quick to respond to messages we sent. 10/10!”

“This might be the 3rd or 4th review i have left for Tzu. She and Niko are the best hosts ever to our pup! The sheer happiness on Ellie’s face when she bounces up to their house is very telling of the absolute madness and fun she has when she is at their place! Tzu is hands down one of the best we have come across on Rover and it is so evident how much she cares about the pups in her care. She sends us little goodie bags of free homemade treats and gives our pup a a quick rinse off when she gets dirty playing out. She is wonderful. I cannot sing enough praises!”

“Haley is the best! I was a very high maintenance dog mom this week because my puppy was recovering from being sick and she took amazing care of him! Thank you, Haley!”

“I cannot recommend Bhairavi highly enough! From the moment we met, it was clear she genuinely loves and understands dogs. She went above and beyond to make sure Oakley felt comfortable, happy, and cared for. I received regular updates with adorable photos and thoughtful notes, which gave me total peace of mind. My dog came home relaxed, healthy, and clearly well-loved! It’s rare to find someone so responsible, kind, and attentive. If you’re looking for someone who will treat your dog like family, Bhairavi is the one. Bhairavi and Gary have a beautiful home and you will not find anyone better to love and care for your dog!! I will definitely be booking again!”

“I felt confident leaving my little dog with Jennifer. She sent adorable photos and updates, throughout the day, made me feel reassured . And the two small dogs got along really well. Definitely book again! Jennifer is wonderful and easy to work with!”

About: Charismatic and outgoing animal lover with 16 years experience owning pets, and hundreds of hours volunteering at the humane society in 3 different states. I grew up with cats, but could not own a dog until I moved out on my own, so I quickly got my first baby Alice the first chance I could. My fur babies include a 13 year old sweet beagle mix, Alice 🌈 and two gentle loving cats, Poppy and Millie. All of my animals have been around other animals their whole lives and get along with all creatures. I prefer not to board cats, but can keep your cat in a closed bedroom for their stay. I would love to open my doors to help out families in need of a more personal way to board their pets when they are away. Your animals must get along with cats and small children. I have a very flexible schedule so I have the ability to care for your pet throughout the day, depending on your pets individuals needs. My pets have free range of the house. Visitors dogs can be crated if needed or have free range of the house if ok left unsupervised.
About: I’ve cared for pets of all ages, from playful puppies to gentle seniors. I provide patient, reliable care and treat every pet like family, ensuring comfort, safety, and love. I work from home everyday of the week except Wednesdays so I have a very flexible schedule to take care of if your pets! On Wednesdays I am usually home before 2pm so your pet would not be left alone for long periods of time ever. Your pet’s safety always comes first. I provide a clean, calm environment, fresh water, supervision, and plenty of love so they feel secure and happy.
“Anusha and her family are too good to work with. Our Pluto was kept very lovingly and utmost care. I kept receiving their playful pics and videos while Pluto was having a good time with all of them. It’s so good and a big relief to see Pluto been left with someone who will treat him with the same love and care that he gets at home. Will be coming back again and again.”

“Jeanne has been amazing! Super flexible with my schedule and Winnie loves her! Winnie gets lots of love and play time, and plenty of potty breaks. Jeanne is always quick to reply when I text too. Highly recommend her!”

“Alisa took really good care of our pups. We needed someone to look after our dogs last moment and she accepted our request. She was very responsive and flexible regarding pick up and drop off timings. We will definitely book her again next time we visit the town.”

About: Our family dog of 18 years recently passed away and our beautiful fenced in yard accessed by a dog door sits unused. Our whole family, including 14- and 11-year-old kids, miss having a furry someone to hang out with. We are all interested in whatever "hangout" may mean ranging from snuggling on the couch, throwing a ball to a great walk! Two spouses with at least one person, and often both, working from home. We start our day early for school around 6:00 am. At least one, and often two, spouses work from home. Most days someone will be at home the whole day/evening. On the weekends we are probably coming and going more but do not have major (day long) commitments. We care for them like they are our own and how they are most comfortable. They can pick a bed for the night with a preferred human or a spot on the couch. We do have a story and a half with three bedrooms accessed by a flight of stairs. The fencing around the yard is a complete metal fence that is "pool" regulation height - slightly taller than a normal fence. There is approximately three inches between slates.
About: I grew up with big dogs, little dogs, dogs that slobbered, and dogs that cuddled. In 2000 our family recused a puppy from a local rescue organization, she was the BEST dog and lived like a princess in our home. I understand senior care very well, as our beloved Schnoodle lived 19 years! I am currently working from home. I get up early and like to walk, can stop midday for a quick walk, and walk in the evening. I live in neighborhood with sidewalks and a park across the street. Currently, I do not have a pet in our home. Dogs are family and will always be treated like a family member in my home. I live in a safe neighborhood with paved sidewalks, streetlights, and a park across the street. I do not have a pet in our home, so your dog would be the main focus. I understand safety measures for puppies, adult dogs, and senior dogs. Gates, crates, leashes outside, food schedules, and I am very comfortable and familiar with administering medicine, especially for senior dogs.
About: I’ve taken care and grew up around Giant Breeds since I was 10. Have owned/loved 1 Great Pyrenees, 2 Great Danes, a large Golden Doodle and currently a fur father to a very lovable and goofy Golden Retriever. Great with dogs of all shapes, sizes, ages, and breeds. Not afraid to squeeze into a shower with a 175 pound dog to keep them fresh n so clean clean🛁. Dogs are definitely this guys 🙋🏽♂️best friends!! I’ve just changed my career path to the sky!! 🛫 I’m in flight school to become a commercial airline pilot. I’m flying and training 3-4 days a week. In my downtime I love hiking and taking our Golden Retriever on fun adventures, so I thought as a side hustle, I could help others with their fur babies and care for them like my own!! You and your pet will always be stress free knowing they are receiving the best personalized care from the moment they or I arrive until you pick them up or come back home to see them. Your pet will be taken care of like family. Constant attention and interaction to keep your pet happy and healthy. Your pet will be fed and walked according to their schedule and access to safe clean and beautiful outdoor space. Your home will be treated with respect and will be cleaner than how it was left. No muddy shoes or paws after playing outside. Paws/shoes will be cleaned. You will be free of worry knowing your pet is getting excellent care and stimulation as well as caring for the home. I go above and beyond for every pet and their owners to keep everyone happy so positive relationships will grow and will have you wanting to book with me whenever you and your pet need help!!
About: I have a house here in St. Louis and go to college at Maryville university. Like every other dog sitter I love dogs and I prioritize my time around them so they can do what they want to do. Dogs will be walked a lot as I go for runs twice a day. I am home most of the time besides when I go in for my classes which are for about an hour twice a day. If I can leave for that amount of time and come back and that works for you then it works for me. I go for morning runs and nightly walks. And weekends I am free There is no limit to where they can explore. I don’t have crazy expensive things so they can wonder around the house or chill with me on the couch. If they walk a lot I can provide limitless walks while I am taking care of them. I love dogs all kinds, and am saving up the money to buy my own. Whenever I eat they will eat or if it’s twice a day that works too.
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 dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
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The median cost per day for doggy day care in Winchester is $30
Why Choose Rover?
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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.
Sitters in Winchester average 4 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 Nov 2025 was about $30 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 Nov 2025, 672 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, 90% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 18 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 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 672 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 95% of sitters offer daily exercise, 99% offer medication administration, and 93% 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.

