Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 60 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 was amazing with Juno and helped out while I was at work for a work trip! Juno had a great time and it was amazing knowing Juno was in great care! Thank you so much!”
“She took wonderful care of my pup with outstanding care and love. She took him on multiple walks and play sessions and sent me a ton of photos. Don’t hesitate to book!🥰”
“Cardinal had so much fun at his small-dog play date!! I appreciated that Betsy took time for a thoughtful meet and greet so that I was sure he would feel comfortable! I was very happy that he could enjoy time outside of his crate with other dogs in a warm and caring environment! Will definitely book again!!”
“My puppies have stayed with Carol a few times and they always have so much fun! She sends me pictures and videos all day and the pups are exhausted when I pick them up which is nice!”
“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.”
“Our dog has a great time with Lee! We were looking for a slower paced daycare option as she gets older (daycare facilities tend to be too overwhelming for her), so Lee and his dog Sharif have been a great alternative for keeping her entertained, but not completely overwhelmed / exhausted.”
“Elizabeth and her kids took amazing care of Bean! Elizabeth was incredibly accommodating in setting up a space for Bean in her home and truly went above and beyond. She also sent various updates and photos throughout Bean's stay with her. Would definitely recommend!”
“Was on a trip to MA for the weekend. Very happy that I found Marcia to take care of my dog for the day while I was out. She provided a lot of pictures and updates without me having to ask. She went above and beyond! She took my dog out for multiple walks as well as letting my dog outside in her fenced in backyard all day. If I am back in MA again, definitely will be reaching out!”
“Ben was great with Pepper! He was able to take care of her on short notice and was very flexible when I needed to change the pickup time from noon to 5 p.m. Pepper came back happy and it definitely looked like she had a great time with him. Really appreciate Ben’s help and flexibility!”
“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!!”
“Thank you Hannah for taking such good care of Milly!! We gave Hannah detailed notes for Milly because she is a reactive dog and we’ve been working with a behaviorist to try to calm her anxieties and fears. She followed them and kept her happy and healthy!”
“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.”
“Elizabeth and Neil made our anxious goldendoodle feel right at home! They were so great with him, gave him lots of love and attention, and communicated excellently with us, sending lots of great photos and videos throughout his stay.”
“I’ve known Junho and his adorable dog Boki since Boki was just a tiny three-month-old puppy, back when we first met in our apartment building. Over the years, I’ve seen how much care Junho gives to Boki, and how gentle and kind he is with other dogs he meets on their walks. When Junho started Rover, I knew right away that I could trust him with T-Rex. My dog requires extra care and attention due to specific conditions, and Junho followed all of my instructions thoroughly. He even sent me multiple photos and updates without me having to ask, which gave me so much peace of mind. If you’re looking for a sitter, I highly recommend Junho. He’s easy to work with, and his wonderful dog Boki will make a great companion for yours. Boki is super friendly and loves to play, but also knows how to give space if another dog isn’t in the mood.”
“We so appreciate Kayla! Our dog was a little shy and concerned about being left behind, but Kayla took care to introduce him one by one to the other dogs, and soon he made a bestie! We will definitely let him stay with Kayla next time we need a doggy daycare.”
“We appreciated Paul’s help with a last minute request to watch our pup for two days over MLK weekend. He was patient with Gracie, as she was getting used to being in a new person’s house.”
“Shuhua took great care of my high energy border collie Jasper! She got him a lot of exercise and had great communication. Can’t recommend her enough”
The median cost per day for doggy day care in Winchester is $50
Dog parents share their Rover experiences - Winchester
Our pup, Sammy, appreciated the kind and gracious welcome from hosts Sahana and Raman -- and also little Cinnamon! The hosts communicated exceptionally well and have a perfect set up for pets. Our first visit was a doggie daycare meet and greet and we have confidence we will be able to do overnight boarding. We will definitely be rebooking!
Carmen did a great job with Finn! She took him for multiple walks throughout the day and took him to some nice spots. He enjoyed playing with the other dogs she cared for. She was also very responsive and easy to coordinate pickup and drop off with. We will book again when needed!
Ben was great with Pepper! He was able to take care of her on short notice and was very flexible when I needed to change the pickup time from noon to 5 p.m. Pepper came back happy and it definitely looked like she had a great time with him. Really appreciate Ben’s help and flexibility!
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!
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.
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 $73.26 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 2,925 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 2,925 sitters in Winchester, 87% 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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