Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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.
“I highly recommend Amy as a dogsitter. She provides exceptional care for my dog, Biscuit, ensuring he is happy and well-cared for. Amy's dedication and attention to detail make her an excellent choice for anyone seeking a trustworthy and caring dogsitter.”

“Kaitlyn was so great!! We got a hold of her pretty last minute and she was more than willing to take our sweet Louie. She took such good care of him and made sure he had fun:) definitely will have her watch him again!:)”
About: I’ve had pets ever since I was a baby and the age of 12 I started my own dog sitting/grooming/training gig. Ive been training, grooming and loving on dogs of every kind ever since! All of my family, friends, and neighbors can depend on me to take the absolute best care of their babies and I thoroughly enjoy it. I am currently working from home so I have full availability and plenty of times to care for and play with your fur babies to ensure all of their needs are met! I currently live in a beautiful home with a fenced yard and plenty of open spaces for playing, walking, and running! Your baby can be kept separately in my home if it would provide more security for you!
“Thank you for taking such good care of Dolly. She looked like she had a great time. It was such a pleasure to meet you. We are in Tulsa several times a year and we definitely would love to use you again.”

“Alecia was amazing she was very communicative and really sweet . My baby really liked her family a lot. The area is great and safe as well I will definitely recommend for anyone that wants a really good experience for there dogs . I don’t leave my boy With anyone now days but with her I trust and I will definitely be back soon thank you Alecia !!!”

“We couldn’t have asked for a better sitter for our 4-month-old chocolate Lab, Dutton! Jesse watched him for the entire day, and it was clear from the moment we picked him up that he had an amazing time. She kept us updated throughout the day with pictures, took him on a walk, made sure he was let out whenever he needed, fed him, and spent the day playing with him. She was incredibly patient and attentive with all of the energy that comes with a young puppy, which gave us so much peace of mind. We truly appreciated the excellent care she provided, and it’s safe to say Dutton loved his day with her too! We will absolutely be booking with Jesse again and highly recommend her to anyone looking for someone who will treat their dog like family.”

About: I’ve been taking care of dogs and cats since i was a child! My family, friends and acquaintances relied on me to care for their animals like they are my own. I’m currently a stay at home mom, and have been using sitter platforms in the past to care for children and animals and have open availability to care for and spend time with your fur babies when you’re busy! I have a fenced in yard and safe inside environment for your pets to ensure a comfortable and safe stay with me with plenty of toys and fun activities for your pet!💗

“I really appreciate the care and attention Miya got while in his care. She was treated like a member of the family and that is important to me. I received pictures and videos and this helped me feel comfortable with Miya being under the weather. I would recommend and send Miya back again and again.”

About: I give elite belly rubs, provide emotional support during thunderstorms, and will absolutely hype your dog up like they just won an Olympic medal for sitting on command. Walks become adventures, naps become supervised cuddle sessions, and your pup will receive enough love, attention, and goofy conversation to forget you were ever gone (sorry in advance). I’m reliable, patient, and very tuned in to each dog’s personality — whether they’re a zoomie-powered chaos gremlin or a tiny old soul who just wants snacks and soft blankets. I also have a kid-free, smoke-free home, so your pup gets a calm, clean, low-stress environment with lots of attention and space to relax. Expect photo updates, happy tail wags, and a dog that’s probably a little disappointed when you come home because we became best friends. Pet care fits perfectly into my stay-at-home routine because I’m home all day, which means your pet gets plenty of attention, supervision, cuddles, potty breaks, and companionship instead of being left alone for long hours. I genuinely enjoy having animals around while I go about my day — playtime, relaxing with a cat curled up nearby, or taking dogs on regular walks and outdoor sniff adventures. Since I have a calm, kid-free, smoke-free home, pets settle in easily and get a low-stress environment where they can feel safe, comfortable, and loved. I’m happy to stick to your pet’s normal schedule and routines so they feel right at home while you’re away. I care for every pet like they’re part of the family — making sure they feel safe, comfortable, loved, and relaxed while you’re away. I follow each pet’s routine closely, including feeding schedules, walks, playtime, medications if needed, and all their little quirks and preferences. Dogs get plenty of potty breaks, exercise, affection, supervised play, and cozy downtime, while cats get a calm environment, clean litter boxes, enrichment, attention on their terms, and lots of cozy nap spots. I’m very patient and attentive, so whether your pet is energetic, shy, senior, anxious, or extra spoiled, I adjust my care to what makes them happiest and most comfortable. Because I have a kid-free, smoke-free home and spend most of my time at home, pets receive lots of companionship, supervision, and one-on-one attention throughout the day. I also love sending photo and video updates so you can relax knowing your pet is happy and well cared for.
“Lindsey was terrific! She was flexible with a last-minute need, was warm and receptive to me, but more importantly with my dog. He is a twice-abandoned rescue has been within 10 feet of me for four years. Lindsey was sensitive, understanding and supportive. She worked to help my dog feel comfortable, and after just a few hours he was sleeping close to her. It's all any loving owner could want, and more!”

About: Hi! I’m Karee and my husband’s name is Jack 😊 We are reliable, caring animal lovers with a safe, comfortable home perfect for your pup’s stay. I work from home, which means your dog will get plenty of attention, supervision, and love throughout the day. I also have two huskies, Tyrant and Maple! They are so sweet and love friends! Jack is amazing at training dogs with positive reinforcement (treats), with commands like sit, spin, shake, high five, and down! I understand how important it is to feel confident leaving your pet with someone, so I always prioritize communication, updates, and making sure your dog feels right at home. Whether your pup loves to play or just relax, I’ll match their energy and routine. We live near Haikey Creek park and Rose West dog park, so your pup can get plenty of exercise if they get tired of the backyard. We would love to care for your pet like they’re my own 💛 I work from home, so your pup will get plenty of love, attention, and potty breaks! We can even go for multiple walks during the day if needed. I have a fully fenced backyard and two friendly pups who love friends! Both of my dogs are crate trained, and we can provide a crate if needed.

“Kameryn did amazing with our corgi! We were unsure how she would do being boarded at a stranger's house for the first time, but Kameryn helped her feel comfortable and was quick to answer our questions. We will be using her again!”

About: I’ve had pets my entire life and have been dog sitting for over 10 years, so caring for them comes naturally to me. I love and admire the unique personalities every dog brings, whether they’re energetic and playful or more laid-back and relaxed. I enjoy staying active with walks, spending time outside in the sun, and playing in the backyard, making sure each dog gets the attention and exercise they need. At the same time, I’m just as happy to slow things down and provide calm, comforting companionship. My goal is always to make your dog feel safe, happy, and cared for while keeping their routine as consistent as possible. I treat every dog like my own and genuinely love the time I get to spend with them. I work remotely from home, which allows me to be present and attentive throughout the day. My flexible schedule means I can accommodate walks, drop-ins, and consistent care routines, giving your pet plenty of attention and supervision while you’re away. Your pet’s safety and comfort are my top priorities. I maintain a clean, pet-friendly environment and always supervise interactions, whether indoors or outside. I pay close attention to routines, energy levels, and behavior to ensure your pet feels at ease. I’m experienced with following specific care instructions, including feeding, medications, and crate use if needed. You can trust that your pet will be treated with the same care and attention I give my own.
The median cost per day for doggy day care in Winchester is $30
Book with peace of mind
- 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.

Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your dogs like family

1. Search
Browse profiles of sitters near you who offer doggy day care
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for doggy day care - Winchester
Select a filter and find qualifying sitters offering doggy day care.Sitters in Winchester average 2 repeat doggy day care clients
FAQs for Doggy Day Care - Winchester
Frequently asked questions about Rover
As of July 2026, there are 169 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 OK 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 169 sitters in Winchester, 85% 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.







