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%.
“What a amazing family! So happy with our experience. Their son even filled out a paw report card for the day. 🥰 They treated Sven like one of the family. We look forward to using them again.”
“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!”
“Estefany did a wonderful job with our Zena. This was our 1st time in doggy daycare so she was very nervous. Estefany stayed in constant communication with me until Zena settled in. I appreciated her good work in helping our pup and making her comfortable! Great job Estefany!! We will be back.”
“⭐⭐⭐⭐⭐ Absolutely incredible first Rover experience! We honestly could not have asked for a better first experience using Rover! We were a little nervous leaving Dodge with a sitter for the first time, especially because he is still a giant puppy with a LOT of personality and, occasionally, some questionable decisions. But Stephanie completely put all of our worries at ease. From the moment we dropped him off, she was incredibly patient, understanding, and attentive with him. She kept us updated throughout the entire day and sent us SO many adorable pictures, which made being two hours away completely stress-free. Every single update and photo made it so obvious that Dodge was having the absolute time of his life. He got to play with Stephanie’s dog and the other dogs she was watching, and he looked so incredibly happy and comfortable the entire time. She even handled his mischievous puppy moments like a champ — including him apparently deciding that stealing her shorts was a fantastic idea. The fact that she could laugh about his antics while still giving him such a fun, safe, and loving day means so much to us. When we came to pick him up, Dodge actually kept trying to go back into her yard! That alone told us everything we needed to know. He clearly had an amazing time and absolutely loved being there. As first-time Rover users, we were nervous about leaving our boy with someone we didn’t know, but Stephanie made the entire experience so easy and reassuring. We came home with a very happy, very tired puppy and so much peace of mind knowing he had been loved and cared for while we were away. We will absolutely be using Stephanie again and honestly couldn’t recommend her enough. Thank you so much for taking such wonderful care of our goofy boy, Stephanie! Five stars from us and from Dodge❤️🐾”
“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!”
“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.”
“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.”
“Jenny was amazing!🤩 Our dog is very anxious and scared and she knew how work with him. When we picked him up we could tell he really liked her! She was very flexible as we were a couple minutes late and very professional and pleasant work with. We will definitely be working with her in the future, our dog was able to cuddle with her dog and received lots of love.”
“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!”
“Tammi is amazing, my dog Luna loves going over and even when I’m booking last minute Tammi always comes through. Great communication and never have to worry one bit.”
“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”
“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 ?”
“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: 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.
About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I don’t have any schedule restrictions I have enclosures for the pet and a larger enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide “nose work” for those dogs that need mental activities.
“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.”
“Briana was amazing! First time for her to take care of my pup for me! She was very attentive and understanding of all of my asks. She sent tons of photos that helped make me feel more comfortable leaving my boy! Highly recommend!”
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
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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 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 1,402 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 1,402 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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