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. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kayla has watched my senior dog several times now. My dog has massive separation anxiety, and Kayla is great with her. Harley seems relaxed when she gets home, which is usually a good indicator that she had a good day. Kayla is also an excellent communicator.”
“Jasper had a great time with Madison and her dogs. She texted me a picture of Jasper while she was watching him and let me know how he was doing. It was easy to communicate with her. I would leave Jasper in her care again.”

“Gunnar had the best time with Sonya and of course her Doodles. If we ever return to visit- I would use her again! Thank you so much for keeping my mind at ease so we could enjoy the parks!”
“Natasha was great! She was quick to communicate, open and easy to work with. She was very responsible and help put an anxious pet parent at ease!! We received updates throughout the day. Highly recommend!”

“Debra was wonderful! I have one dog who is very anxious and she was so patient with him to make sure he was going to be comfortable in a new environment. She has a wonderful fenced backyard which was important to me as my anxious dog doesn’t do well on walks. I will definitely be using her again.”

“Casey was the best with our pup, we traveled from out of state and was in need of a sitter while we took care of business and attented a family graduation. Casey was so caring to our pup, gave me updates along with pics everyday. I highly recommend her for doggy day care.”

“Ollie had a great time! Brent sent pics and was a great communicator! If we're back in Lexington, we will definitely have Ollie stay here again!”

“Cheyenne took wonderful care of our Jax. He had a blast playing with her dogs and made a new friend, Romero. Her kids took to him right away. As labs do, he got muddy and she went over and above by bathing him. She sent frequent pics and videos of him playing. We will definitely use her again if we are in the area again.”

“Emily and her pups were great! She was very welcoming and flexible with her time. She has an amazing fenced in yard. I felt very comfortable with her, and she was very patient and worked with my dog to get her settled. My doggie was very anxious, and Emily was very patient! Already have another booking with her for boarding!”

About: We've owned and cared for dogs for over 35 years. Our first dogs were a Lab and a Golden Retriever then a Pug and a Puggle and now the parents of a Lab/Husky mix. We provide loving care with plenty of exercise in our non-smoking, fenced home. We live one block from Jacobson Park and its wonderful dog parks so rest assured your fur baby will receive plenty of attention, exercise, fun and love during its stay. I work from home and my spouse is a stay at home spouse, so we are available to provide constant care, exercise, play time and supervision for your fur baby. Whether is romping in the fenced yard or walks to the dog park, your furry friend will enjoy being part of the pack with our dog. Our fenced yard and quiet cul de sac on a golf course and located a block from 2 dog parks is a great place for your dog to stretch its legs and play to its heart's desire. During warmer times, we'll also spend a lot of time relaxing with your pet in our screened in deck in the back yard with access to our fenced in yard.
“Laura did a fantastic job watching my puppy Alma! She watched her for multiple days and each day Alma came home a happy pup. I got a detailed report on the day and felt very secure trusting Alma in her care.”

“Kristin and her husband were great! My dog had a blast playing with their dogs and came home happy and tired. You can tell they truly care about dogs—highly recommend.”

About: Hi, My name is Casey and I would love to be able to take care of your animals. I love all kinds of animals! I can provide any of the services listed. I am not new to taking care of animals and I have house sit for people before. I work full-time on this app. If you have any questions please feel free to message me! I have two cats and two dogs at home so I spend plenty of time with all of them by playing with them, feeding them, showing them new activities, and spoiling them! We have a fenced in back yard. I always listen to instruction's so anything your pet needs I will be happy to help with! Always looking forward to meeting new animals!
“Ashtin & Jenison have completely won me over as a helicopter parent. I truly feel like my dog is safe and cared for with them. They are very trustworthy and knowledgeable. I cannot recommend them highly enough!”

About: Ive had a total of 2 dogs and 1 cat and 2 kittens. Also I have pet sat a variety of animals from cata and dogs to even snakes. All well taken care of and loved. I know exactly how important our little friends are and I would protect them and take care them as my own. I am currently on leave from my regular job so I have all the time in the world to pet sit and it would work in well with the daily walka I take my own child on. I have a two different parks very close to my home that I tale my child and a baby gate to ensure that no one will go anuwhere unsafe.

About: I’ve had dogs since I was a kid. I’ve cared for friends and families dogs of all sizes and ages. I currently have a female American bully but in the past I’ve had English mastiffs, pit bulls, and a border collie. I enjoy high energy dogs that love to run and play as well as older dogs that just want to play around and be loved on. I’m currently on summer break. I am an athlete at Eastern Kentucky University and have required practices every day but I’m gone no longer than 3 hours per day. I currently live in an apartment with a dog park on site I also have one friendly and very active pup to keep yours company. I will always be outside with the pups they are never out there alone.
“Guadalupe was great with our girls. So easy to communicate with, kept us updated with pics and videos and even provided a great restaurant recommendation. If we come back through Lexington, we will return to Guadalupe.”

About: Hello there! My name is Angie and I'm a pet sitter in Lexington, KY. When you hand over the leash, you deserve to feel completely at ease. I’m Angie — a reliable, trustworthy sitter and walker who genuinely loves dogs — and as a dog owner myself, I know exactly what pet parents need: clear communication, consistency, and someone who actually cares. I offer dog walking, drop-in visits, boarding, and house sitting, and I’m comfortable with all sizes and breeds. My home has a fully fenced yard, so boarding and visits are safe and stress-free. I keep my schedule flexible to work around yours, and you’ll always get photo and update check-ins so you can see your pup is happy and thriving. Your dog won’t just be watched — they’ll be loved. I’m retired, so I’m home all day and your pup won’t just be sitting around waiting for me. I’ve got nothing but time for belly rubs, walks, and cuddles. Your fur baby will be treated like family, because honestly, that’s just how I am! I have a fenced in yard of over 1/2 an acre with two friendly dogs! We will have playtime outdoors and they can come and go as they please with the doggie door
Over 17 pet parents in Winchester have booked doggy day care
Winchester dog parents share their Rover experiences
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1. Search
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The median cost per day for doggy day care in Winchester is $30
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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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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 $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 Jun 2026, 148 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 148 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 93% of sitters offer daily exercise, 93% 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.



