Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 29 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.
“I just got my first dog and was super nervous having someone watch him for the first time. Jeanne made it much easier and I feel very comfortable letting her watch my pup. I will be booking her again!”
“Alvin loves going to Beth’s every day! He is so in tune with morning routine of getting ready and out the door! He’s ready to go before I can get a cup of coffee. He loves being with the friends he’s made and all of the great exercise he gets! Thanks to her family for loving our Alvin!”
“Lorri took such great care of Charlotte and kept us updated through the day. We so appreciate your loving care & look forward to Charlotte’s next stay with you! Thank you so much!!”
“Raven had a wonderful stay with Greg and Jane. This is a perfect situation for her as she is nervous around other dogs but is comfortable around people. Greg had a sharp eye to get her out for walks duriing the period and in general provided for a tranquil stay. She was in a great mood when I picked her up and Greg had walked her just before my arrival so that she had already gone potty before I came. I'm thrilled with Greg and Jane's attentive care and will try to see if they are willing to care for her in the future. Thank you!”
“Ursula and Dalia are both lovely and very welcoming! My doggie always enjoys his visits with them and meeting new friends who come to stay. I highly recommend them!”
About: I am a very loving and nurturing host. I work full time so I'm available from 6am to 8am during the week, and also in the evenings & on the weekends. I offer personalized care for all dogs. Let me know what your preferences are. I am happy to work with you. I look forward to meeting you and your fur baby! I work full time, so I am available from 6am to 8am during the week, as well as in the evenings and on the weekends to walk your dog, feed them, and take them out. When I take care of other dogs, I treat them like my own dogs. I am patient, loving & kind, and love taking care of dogs.
“Holly is so kind and caring! My dog loves going to her house. She watched him for me while I am at work. I really appreciate her flexibility with my schedule since it changed every week. She send photos of my dog throughout the day to keep me updated. Super happy I found her and will continue to use her to watch my dog.”
“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.”
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 spent a career in hotel hospality and will bring enthusiasm, patience, professionalism and love to every interaction. I'm considered "the dog whisperer" at the dog park and currently walk a few dogs in my neighborhood for those who simply physically cannot. Acts of service bring me joy, thus pet and pet parents top the list. I'm a full-time father of a thirteen year-old daughter. If I'm not transporting her to and from school, I'm available. My weekends and Holidays are open. I have a field next door and wonderful neighborhoods with walking trails right outside my door. I have a small very sweet husky mix that can be crated if needed
“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!”
About: We’ve loved meeting all kinds of dogs through Rover, whatever breed or size, and we’d love to spend time getting to know your furry friend through walks, cuddles, and just being together! We’ve had several dogs over the years from an 11 lbs. Schnoodle to an 80 lbs. GSP to now Oliver, a 50lb. mix of many breeds. (However, he can go two-doors down to my father-in-law‘s house if our furry friends don’t get along.) We hope to meet you soon. Amy currently works mostly from home with a very flexible schedule. We get up around 6AM in the morning and stay up until about 10PM. We’d love to get steps in by taking your pet for a walk! Carl also often stops home throughout the day. Wehave a screened in back deck and also a fenced in area below that is shaded. Your pet can find the perfect place to relax and enjoy, weather pending!
“Iliana and her family were absolutely wonderful! This was my first time ever leaving my dog with someone other than myself and Iliana was so caring and kind to my doggie and myself. She sent me pictures and updates throughout the day, which was awesome and comforting!”
“Sarah was amazing with my baby Soup! She is super friendly and very responsive. She took care of Soup like her own and sent lots of pictures and updates, which I really appreciated. I felt completely at ease the whole time. Highly recommend her! 😊”
“Melinda was very accommodating and Eli loved going over there. We would jump out of the car and I would follow him to the front door. Thank you so much and I will definitely use her again.”
About: Hi my name is Hattie and I would love to watch your pup!! I have grown up with dogs all my life and have had a lot of experience watching dogs of all sizes and ages (and cats too!!). I currently have a 6 year old Italian Greyhound who is full of energy and would absolutely love to play with your pup if they’re up for it! I am a night shift nurse and my fiancée works from home so our schedule can be a little weird, but there’s almost always someone home. I would be happy to watch your dog, stop by to visit, or take them on a walk or to the dog park. Let me know how I can help you and your dog! Message me with any questions you have:) I currently work night shift three nights a week where I am gone all night but my boyfriend works at home during the day so there’s always someone home! I have a fenced yard that is fortified to keep my own 10lb dog from slipping through! She likes to come in and out all day and lounge on the deck when it’s nice out.
The median cost per day for doggy day care in Winchester is $30
Dog parents share their Rover experiences - Winchester
Raven had a wonderful stay with Greg and Jane. This is a perfect situation for her as she is nervous around other dogs but is comfortable around people. Greg had a sharp eye to get her out for walks duriing the period and in general provided for a tranquil stay. She was in a great mood when I picked her up and Greg had walked her just before my arrival so that she had already gone potty before I came. I'm thrilled with Greg and Jane's attentive care and will try to see if they are willing to care for her in the future. Thank you!
I cannot say enough wonderful things about Jessica and the loving care she gave Izzy at daycare. Leaving Izzy with someone else can be difficult because she is such an important part of our family, but Jessica made us feel completely comfortable and Knowing that Izzy was safe, happy, and well cared for gave us true peace of mind. Izzy came home happy and relaxed, which showed us how comfortable she felt with Jessica. We are deeply grateful for Jessica’s kindness and the special bond she created with Izzy. Finding someone you can trust with your fur baby is priceless. Jessica truly has a beautiful heart, and we highly recommend her to anyone looking for the best care for their pet. Thank you, Jessica, for loving and caring for our Izzy so wonderfully!
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 4 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 September 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 September 2026, there are 714 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 MO 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 714 sitters in Winchester, 84% 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.
Connect anywhere with the Rover app
