Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 50 pet parents in Winchester have booked doggy day care
Winchester, Find top rated doggy day care
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Tammi was awesome! First time I ever dropped off Hope for day care the sitter offered me to tour her home to see what it’s like for the doggies inside 😊 that was much appreciated! Tammi is a very experienced trainer apparently and that gave me more comfort to trust her with Hope. Will definitely book with Tammi again when we’re back in the area”
About: Im home 24/7 so you need a sitter dog, walker im there 😭 all I do currently is take care of 4 dogs. Always make sure they get their walk so they stay fit, I never over feed, make sure they get their outside play time and nap time I am on it. I currently have plenty of spare time so im very free everyday to go on walks, play take care of a dog whenever needed. Currently do that right now with my own little weiner army all I do all week is take care of dogs. I have 4 small weenies who love to dig and play in the big back yard and i take them on walks every day or every other day depending on their energy. They do mostly love to sleep throughout the whole day and dig.
“Tashia was such a great caretaker for our beagle! Our beagle had such a fun time playing with the other dogs - Tashia sent photos and video! You can tell Tashia loves animals and cares about your pet…..we will book her again.”
“They were awesome with being able to accomadate me so last minute! They provided me with pictures and updates and I know he was in good hands. Levi was so happy to stay here and I definitely hope to get their help again soon!”
“Sandra and her home are very welcoming and we appreciated her making the time at a last minute stay. Sandra made sure they had their potty breaks, got exercise, and ate well. We got updates and let us know how the day went”
“We were very pleased with care provided. Frank, Saleha and their children were very welcoming and both Maya and Chiquita seem happy to be there. In particular, Chiquita, our 15 yr old did not show any anxiety or stress, on the contrary and Maya seem to enjoy the company. We would definitely feel comfortable leaving the girls and recommend for others. Thank you!”
“Our Bear was in the very best hands! We received messages, pictures and videos throughout the day which we loved! It was comforting to know he was having a blast with the other pups and felt comfortable in their home. Cannot recommend enough!”
About: I've been caring for my own dogs for the past 9 years, making sure they get daily walks, plenty of exercise, and weekly trips to the park to keep them happy and healthy. I've also cared for a variety of dogs ands cats while friends were out of town, providing reliable, loving care and giving owners peace of mind because I know how stressful it can feel leaving your pet with someone new. I genuinely love pets and enjoy spending time with them. Whether your pup needs a fun walk, exercise, or a little extra attention, I'll treat them with the same care and affection as if they were my own. I have a flexible schedule and am available seven days a week. Since I work from home, I can accommodate morning, afternoon, or evening walks and visits. I'm happy to work around your schedule to provide reliable, consistent care whenever your pet needs it. You can always expect clear communication and timely updates and photos. Your pet's safety and comfort are my top priorities. Pets will spend most of their time indoors in a safe, comfortable environment. They'll be taken outside for regular potty breaks and exercise, and they'll always be supervised while outdoors to ensure they stay safe and secure. I'll treat your pet with the same care and attention I give my own.
“OMG!!!! Demelia was amazing with our dog from day one till we picked him up. She was very personable, love what she does, & kept us informed throughout. She sent us live videos daily of our dog having his walks, playing time with her dog “Moon” who’s also amazing, & cuddle relaxing time. We couldn’t have asked for a better sitter. We would definitely book her again & again. Thank you so much for loving on our dog like he was your own.”
“Nicole is absolutely amazing! She was so kind, understanding and accommodating. She provided plenty of photo and video updates throughout the day and I loved seeing how happy my baby was while I was away. Our puppy Stella had an absolute blast playing with Nicole’s doggo Sunshine each day during her stay! She finally made a new friend who can rival her energy. Each morning she was so excited for drop-off with her new friends and each evening she came home happy and thoroughly worn out, which is really saying something for our little furry ball of energy! Stella already can’t wait for her next visit with Nicole and Sunshine. Nicole is a quality, caring sitter who I cannot recommend enough!”
“I needed a dog sitter as soon as possible and was running out of time. She accepted my request, and I was very happy. She sent me updates during the day on how my dog was doing. He even got a report card at the end of his visit. I definitely recommend Darlene for your pet-sitting needs.”
About: Hi 👋🏾 , my experience with pets goes all the way back to my childhood. I got my first poodle in the 3rd grade who I took care, feed, and groomed. Additionally, I had two other poodles growing up and a golden retriever who I helped raise and train. I’m knowledgeable in caring for dogs and cats. Currently I have two cats and two dogs who are all well adjusted to welcome visiting pets. I work from home and have plenty of time to go out to the yard to monitor play time. When visiting your pet will not be left alone. I have a fenced yard and my two dogs are very friendly. I have a crate and a puppy space in case you pet needs it and a large stock of pee pads.
“Thank you so much for watching my dog on short notice. Robert sent update photos throughout the day, was quick to respond, and gave me ease that my pup was in good hands. Thank you to you and chief!”
The median cost per day for doggy day care in Winchester is $44
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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Reservation protection
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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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
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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 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 $38.85 per day (as of August 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 August 2026, there are 1,385 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 CA 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 1,385 sitters in Winchester, 89% 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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