Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 8 pet parents in Winchester have booked doggy day care
Winchester, Find top rated doggy day care
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.”
“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!”
“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!”
“We’re so lucky to have Casey looking after our precious little fur baby!! She’s always so attentive, super responsive and takes amazingly cute photos!! She takes really good care of Coco and we just know Coco is gonna have a great time when we drop her off. Highly recommended!!”
“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.”
“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: After experiencing the tragic loss of my own cats due to a negligent pet sitter, I became deeply committed to providing the highest level of care for all animals. That experience taught me how vital it is to entrust pets to someone who not only understands their needs but treats them like family. I specialize in senior pet care, offering compassionate support for aging pets, including administering medications, managing health conditions, and providing gentle, tailored exercise routines. I also have experience training puppies, helping them develop good behaviors early on and ensuring they have the structure they need to thrive. My focus is always on building trust and creating a safe, loving environment for your pets, so they feel comfortable and secure when you're away. Above all, I aim to offer peace of mind to pet owners, knowing their animals are in caring, responsible hands. Available almost anytime in Lexington and surrounding areas contact in advance is recommended but we can take last-minute calls depending on the situation and what not. Also I work with you budget! I have a park near me and I do take my own dog to the dog park every chance I get via Lyft and plenty of toys for your fur babies!
“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!”
“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!”
“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.”
About: I’ve owned multiple disabled dogs and can care for them. I’m also experienced in giving medicine to animals that may need it. grew up around a lot of different animals and I love spending time with new animals and seeing all the different dog and cat breeds. 😁 I stay at home and my schedule is very flexible, so the fur babies will get plenty of attention and love! They will always have me with them for some company and play time. I can take care of pets in any way that their pet owner would like. I don’t have many rules and would just like for the fur babies to be comfortable in the new environment!
“Ashton and Jamison were great! They took great care of our senior dog for the day and snuggled up with him. I’m so glad he had loving people to spend the day with.”
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.
“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: I have genuine love for animals and treat every pet like they’re my own. I’ve always loved being around them and caring for them with patience and attention. I have experience dog walking, feeding, playing with pets, and making sure they feel safe and comfortable while their owners are away. I understand how important routines are for pets, and I do my best to keep things consistent so they feel relaxed and happy. Im going to be a senior this year at Lexington Christian Academy and have a part time job at the Ymca. Im available during the week 4-10pm. I have a big fenced in yard with a small dog and cat. They are both very friendly towards people and pets. always put pets’ safety and comfort first. I carefully follow pet parents’ instructions and stick to each pet’s routine. Whether in my home or a client’s, I keep the environment calm, clean, and secure, and I closely supervise pets during walks and playtime. My goal is to make every pet feel safe, comfortable, and cared for. 🐾
About: We came across the Cavapoo breed as our loving Rottweiler was on his journey to his “better place”. We chose the Cavapoo breed as our furry rainbow puppy to help us all with the tough loss. Fast fwd 5 years, and WOW, still can’t believe the journey that was created for us. Dog breeding, training, boarding and grooming just the way I would want my pups taken care of…in a home. Our setup is ready for all stages of dogs and of course, personalities. This is a small family business and we make pet care fit seamlessly into our lives. We’re a party of 4 and all hands are always on deck. 4:00 am wake up call during the week and 6:00 am on weekends. Caring for pets in our home can consist of taking your pets normal routine that’s already established and following it. Help keep your animal on a schedule of food timing to crate or bedroom boarding. We live in a neighborhood with a 6 foot privacy fenced in back yard. A 3,000 gallon Koi pond surrounded by 800 square feet of deck. Nice plush outdoor furniture for the dogs to lounge next to the pond after a drink. We have also built a 200 square foot doggie palace on our property. Full electricity with heating/air and additional ceiling fan. Great for rainy days or dogs who are lone rangers and/or feisty.
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!
The median cost per day for doggy day care in Winchester is $30
Dog parents share their Rover experiences - Winchester
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- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 3 repeat doggy day care clients
FAQs for Doggy Day Care - Winchester
Frequently asked questions about Rover
The average cost for Doggy Day Care in Winchester on Rover is $27.75 per day (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Doggy Day Care easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Doggy Day Care. For more information on service fees, click here .
As of July 2026, there are 173 sitters on Rover offering Doggy Day Care across Winchester. Enter your ZIP code to see which available sitters are closest to your home.
Sitters on Rover can offer flexible scheduling, so you can coordinate times that work best for you and your pet—whether that’s early drop-off or later pick-up to match your Winchester commute.
If your schedule changes, it’s best to let your sitter know through the app as early as possible. Many sitters can adjust pick-up and drop-off times when needed.
Think of doggy day care as your dog’s fun, supervised play date that happens to fit into your workday. Day care through Rover takes place in a real home. This offers a calmer and more personalized environment for your pup.
A typical day can include companionship, one-on-one attention, and same day pick-up and drop-off. Many sitters can also offer structured routines and exercise throughout the day. For recurring, weekly day care, sitters will include photo updates so you can see your dog in their element.
Here are tips for finding the ideal day care fit for your dog:
- For some small dogs: In-home day care can be the perfect fit. Look for sitters whose "can host" section only lists dogs weighing 0–7 kilograms and/or 7–18 kilograms. During your Meet & Greet, ask about play areas based on dog size and energy level.
- For high-energy dogs: The ideal doggy day care can offer scheduled breaks and outdoor spaces or activities. You can also find sitters who host multiple dogs to satisfy your pup’s socializing needs.
- For dogs who prefer human-only companionship: Use the filters "Doesn't own a dog" and "Only accepts one pet at a time" to find the right care.
Play groups can be an option when you book with a day care sitter through Rover. Many sitters do host a small number of dogs at the same time. Smaller dog packs are generally safer, more fun, and ideal for dogs who enjoy playtime but also want to relax throughout the day. When looking for your dog’s pack, check the sitter’s profile to see if they "Accept multiple clients" or have their own dogs. Then during the Meet & Greet, you can see whether your dog is a good fit for their social circle!
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in KY ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 173 sitters in Winchester, 81% respond to messages in under an hour.
You can message multiple sitters simultaneously to find the fastest available match. If you need care today or tomorrow, you can look for sitters with a "calendar last updated" notice on their profiles.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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