Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 30 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%.
“Belinda took great care of our dog Ollie and sent regular updates and pictures. Ollie is an anxious dog and he seemed very comfortable there. We would definitely have him stay with her again!”
“My pup had the best time ever in the yard, chilling in the house, and befriending Betsy’s sweet dog. I even got a photo during the day. :-) Looking forward to her next stay!”
“Took my greyhound, Judy, to stay with Luci and her family for 2 doggy daycares. Judy is typically timid around new environments but warmed up quickly to them and absolutely loved spending time with everyone and the other dogs being watched. Definitely will be using Luci again!”
About: Master's degree in animal care and welfare. Former vet tech for dogs and cats at an E.R. I also have an Animal Science degree and have cared for horses and other animals. I work from home some days, part-time, and always have walk breaks. I go for long walks and will join with doggy playmates if your dog is able. Will also walk small dogs in carriages for fresh air. Have fenced in yard for small and medium size dogs. I have a fenced in yard and one Bichon rescue dog who is older, and friendly with other dogs. I was a former vet tech and have much cat and dog health care skills.
“This is Scout's second time at Jacqueline's for doggy daycare. She and Harley do an amazing job looking after Scout. Highly recommend her, she treats your dog as if it were her own.”
“Finn has been loving his days with Likun! Her dog loves to run and play as well, so it’s a great match! Finn gets outside time, walks, and naps during his stay and always comes home tired and happy. Thank you Likun!!”
“Janette and her family, including their dog Luna, are so wonderful to our dog, Lenny. She is so kind and communicative! Lenny loves spending time with them and going for walks in their beautiful neighborhood. Thank you so much for taking such great care of our dog!”
“Wonderful family who provided care for my pup last minute. They sent me pictures throughout his stay and he appeared happy and tired from all of his play with their other dogs when I picked him up!”
“Elizabeth and Rodrigo were great with Oscar. They were flexible when I needed to shift my drop-off and pickup times, which made my day so much easier. They sent a few photos throughout the day too, which I always love getting. Oscar came home tired and happy, so he clearly had a good time. Would book with them again in a heartbeat. Thanks you two!”
“Ben and his family took great care of Zelda and were very accommodating of our busy schedule. She came home happy and well exercised from playing with their pups all day. We will definitely book with Ben again!”
“Cheuck was an excellent sitter for our dog Simka. We basically never leave her with someone we don’t know, but he made us comfortable from the beginning and she had a great time. It was fun to see photos and videos throughout her stay.”
“This was Marley a first official visit. We did a meet and greet a few weeks ago. Marley loved his visit. He did the doggy daycare and he wanted to stay, which is always a good sign! Elizabeth and Neil sent me picture and videos which was nice to see. Illy little guy got home and went straight to taking a nap because of all the fun he had. He loves being outdoors and with their big fenced in yard he was completely in love! Marley will definitely be a regular from now on! Thanks Elizabeth and Neil!”
“My dog had a wonderful stay with Xiuping and her family. They are so kind and friendly. Very responsive and trustworthy as well. I got many cute pics and felt my dog was given a lot of attention and well cared for. I would definitely rebook next time.”
“A truly 5 star experience. Cameron was easy to communicate with and work with. Just off vibe alone I knew my dog was in good hands when he was picked up. Throughout the day I was consistently updated with photos and videos of my dog out and about. I highly highly recommend Cameron to anyone in need of a dog-sitter. Next time I’m in Boston I will 100% be reaching out to him first. Finn will miss Cameron and Rosie a ton!!! 5 stars!!”
“Lexi took great care of Emmy during her daycare visit! She was very attentive to Emmy’s needs and made sure she felt comfortable and happy throughout the day. We appreciated all of the updates Lexi sent us during the visit!”
“Marcia was absolutely wonderful! She is incredibly kind and clearly loves animals. I received frequent updates with photos and videos throughout the day, which really helped to ease my mind. I loved the videos watching my dog, Mylo, get to play with Marcia and Cosmo! My high-energy puppy came home happy and exhausted, which is the best compliment I can give considering Mylo’s energy level! I highly recommend Marcia to any pet owner looking for a loving and responsible sitter.”
“Fantastic puppy sitter!! Jasper loves going to play at Carol's and comes home exhausted. I love knowing he's well looked after, happy, and safe. Great communication and pictures. Thank you so much!!”
The median cost per day for doggy day care in Winchester is $50
Dog parents share their Rover experiences - Winchester
Unfortunately, one of my dogs has cancer and I have a week of early morning trainings for work. (530a drop offs- Yikes!). Yesika is still willing to take her every day, work with the energy that she has that day, and offs care across the day (additional small meals, medication for nausea,etc). So glad that I have this resource.
Janette and her family, including their dog Luna, are so wonderful to our dog, Lenny. She is so kind and communicative! Lenny loves spending time with them and going for walks in their beautiful neighborhood. Thank you so much for taking such great care of our dog!
Sophie had a great day with Andrew! She had a few nature walks that I can never give her. She loved her day away from home. Andrew is excellent to work with and incredibly professional. He was consistently quick to respond and sent lots of pictures of their day together. Andrew had Sophie this summer for a long weekend and Sophie returned home happy as could be! It's as though she was with family. Thanks, Andrew, for making her days so enjoyable!
Brianna has taken such good care of Oliver at a really hard time for him. He is so happy to see her and her home is such warm and cozy for my dog. She communicates perfectly to let me relax after I drop him. You can tell Brianna really loves the dogs she cares for.
I recently moved to MA from out of state with my male pup, and connected with Kayla for daycare service. Kayla is experienced in providing care for pets. During my pup’s stay, she was accommodating and took such great care of my pup. She even gave him 2 doggie chew sticks, and he was so excited to take those home with him! ☺️ 🥹 Kayla is the best!
Olivia & Robin were stellar dog sitters and kept me posted on Rosie's first stay with photos and updates throughout the day, which put my mind at ease. They gave her lots of love and attention, making her feel right at home. She was very tired and happy when I picked her up, which is always a great sign. I will definitely book with Olivia again!
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer doggy day care
2. Meet & Greet
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 3 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 $36.63 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 2,964 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 MA 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 2,964 sitters in Winchester, 86% 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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