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!:)”
“She did amazing! I was nervous about leaving my pup w a sitter for the first time. I appreciate knowing he's in good hands when I need someone to take care of him. We will be back. :)”
About: I have had dogs all my life. Growing up we had Golden retrievers, and since moving out and having my own family I have a 4yr old doodle mix and a rescue pup. I love training them both, I like to call them my little circus pups! I have vast experience with dogs, there has never been a time in my life when I havent had a dog at home. We even brought coco, our doodle over when we moved from the UK3 and half years ago. There was not a chance I was leaving without her. My home is always open to friends and family when they are in need of pet care and they are always treated like royalty. I would love to be able to do the same for you. I am a stay at home mom with the occasional doordashing job when I can. I can provide petcare whenever needed. Free to take care of your pet at a moments notice, no ties or commitments that cant be shifted around to make space for you. I have a fenced yard and a beautiful walking trail right out the back of my neighborhood for long strolls and open space for dogs that are able to be unleashed. I do have 2 dogs at home who are very friendly, so pups that are good with other dogs are always welcome. For those who are not I can accommodate by coming to you. Whatever you need we can make it work.
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.”
“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.”
“Glad my first Rover time was with Tori. We met a few days beforehand to introduce my pup to hers and everything went smoothly from there. During my dog’s stay at her house, Tori was communicative and responsive to my messages. She frequently sent videos and pictures, which eased my concerns as a first-timer. I never write reviews, but I wanted to reassure readers that she’s a sure bet. Thanks Tori! 🩵”
About: I've had dogs all my life, lived on a farm , i know a lot about animals and I am very reliable and flexible. Have pet sit for friends, family, ect I have a small yard, and dog that loves to play. I am able to crate your pet if needed, otherwise , it's all dog friendly 😊 my availability is open and flexible. I can accommodate your pets needs .i am located in Haskell area, and can travel to your pets or home . I have a yard , and a teenager to keep your pet busy and entertained! I have plenty of dog toys and snacks and we love to pets on an evening walk.
About: Dogs have been a part of my life since I was a child, and I was lucky enough to have my dog, Sadie, for 11 years. I adopted her when she was just one year old and trained her myself. She passed away in August of this year (2026). One thing that has truly shaped me as a pet owner was caring for Sadie after she became disabled three years ago. That experience taught me patience, compassion, and how to recognize the little things that can make a big difference in a dog's comfort and well-being. From helping with mobility challenges and maintaining daily care routines to noticing subtle changes in behavior, I've learned how important it is to understand each dog's individual needs. I know every dog has a unique personality. Some want to play all day, some prefer quiet companionship, and others need extra patience or a little additional care. My goal is to help every dog feel safe, comfortable, and loved while you're away. Right now I'm offering drop-in visits and house sitting in your home. I'll treat your dog like one of my own, and I'll be sure to send a few pictures and updates along the way so you can see how they're doing. I work full-time from home and have a flexible schedule, which allows me to be available throughout the day for potty breaks, walks, playtime, and plenty of attention. Because I make my own schedule, I can easily adjust my day to meet your dog's needs. I know dogs are usually most comfortable when they can stick to their normal routine, especially when their people are away. When caring for your dog in your home, I'll follow the routine and instructions you provide, including feeding, potty breaks, walks, medications, playtime, and bedtime routines. I also like to learn the little things. Where they like to sleep, their favorite toys, what makes them comfortable, and any habits or quirks I should know about. I'll respect your home and do my best to keep things comfortable and familiar for your dog while you're away.
About: I treat every dog like family! I have experience with all ages—from playful puppies to sweet senior dogs who need a little extra care. I’m patient, attentive, and trained in basic commands and medication support. Whether it’s belly rubs, walks, or special diets, I’ve got it covered. 🐶💛 Pet care is a natural part of my daily routine—I genuinely enjoy spending time with animals! I make time for play, walks, feeding, and cuddles just like I would for my own pets. Whether it’s early mornings or evening check-ins, I’m flexible and reliable to ensure your pet stays happy, healthy, and loved every day. 🐾💛 In my home, I provide a safe, clean, and cozy environment where pets can relax and feel at home. They get plenty of attention, playtime, and a structured routine that includes walks, meals, and quiet time. I follow any specific instructions you provide to keep things consistent.
“Katherine boarded my 10 month old black lab (we provided crate, food, favorite toys, leash, ect). She did an amazing job while we were out of state for 7 days! The fact that they have a fun and playful Australian Shepard ages 1.5yrs, that my puppy could play with all day, really helped him enjoy his stay! They seemed to al get along great! Katherine provided a fun environment for Oliver. She walked him and let him play in their large backyard each day, even in the heat! She sent daily updates via text with photos and helped put our minds at ease for our pup while we were gone.”
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?
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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 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
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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 September 2026, there are 172 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
Yes, Rover is well-suited for finding sitters who can care for your pet within 24 hours. With 172 sitters in Winchester, 87% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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