Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 75 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 amazing, I was very nervous leaving my pup for the first time ever with anyone. Tammi made me feel such at ease and comfortable and relaxed. Knew everything she needed to know with my pup. Will definitely be booking from now on.”
“Paulena took wonderful care of our dog! He was always excited to see her and had so much fun playing with the other dogs. She was flexible, easy to work with, and kept us updated with great communication. We’d absolutely recommend her to anyone looking for a caring and reliable pet sitter!”
“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.”
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.
“Wow! This was by far the best rover experience I have had. Not only did I receive a fast response for a last-minute booking but she was extremely flexible with my schedule. And of course even more important, my fur baby love her! She has never revisited a sitter and been excited to go but on her second visit she was wagging her tail and had lots of energy. I also appreciate all of the updates, pictures, and videos as this helps to put my mind at ease while I am away at work during the day. I look forward to making this my regular sitter !!”
“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!”
“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.”
“Had an emergency needed a sitter and she responded within minutes. She took care of my puppy for about 3 1/2 hours my puppy looked happy when we got him back gave me an update on how he was doing while sh had him really nice and assured me he was in good hand! Thank you Chanelle ?”
“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!”
About: I've been taking care of my dogs for 7 years taking them on daily walks and weekly park visits for their enjoyment. I have taken great care of many breeds of dogs to help friends when out of city. I love dogs and would love to help with their walks I'm available at any time all week, I can schedule your pet either morning or afternoon and weekends. I work from home so I'll be available at any time, any day of the week Pets will stay inside most of the time and going outside for potty but supervised all the time to make sure they are safe always
“I highly recommend Vincent’s Doggy Day Care. They have amazing communication with the pet owners, which is fantastic for someone like me since I don’t like being away from my fur babies. Vincent sent pictures throughout the day as well. Again, this helped ease my mind knowing both my babies were alright. Pricing is very affordable for the service you receive. Go with Vincent. You won’t regret it. I definitely will be bringing my babies back to see him.”
“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!”
The median cost per day for doggy day care in Winchester is $44
Dog parents share their Rover experiences - Winchester
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 near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 5 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 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 1,429 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 1,429 sitters in Winchester, 90% 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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