Doggy Day Care Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Over 31 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!”
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.
“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!!”
“Elizabeth and Neil have been great with my dog Teddy. They have a great home and fenced-in back yard for Teddy to play in. I can tell that Teddy loves them and in comfortable with them. From my first meeting with Elizabeth and Neil, I knew that their Doggy Day Care was going to work out well for Teddy and me. They are very responsive to my texts and answered all of my questions with kindness. Teddy and I look forward to seeing them next week! Glenn”
“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.”
“Another great stretch of daycare days with Likun and EL! He races to her house every morning which tells me he loves going! I can go to work knowing he’s in good hands. Thank you again!”
“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!”
“Our pup, Orla, enjoyed her time at Carol's. Carol was super sweet and her home was lovely; Orla enjoyed the fenced-in turf backyard quite a bit from the video Carol provided. Everything was smooth and went well. Thanks again!”
“Ying is so sweet to our pup and makes sure she has everything she needs throughout the day. We love receiving photos and updates and Ying is great with them. We will definitely be booking again!”
About: Since coming to college, I’ve started volunteering at the Humane Society where I’ve been day-fostering! Love dog sitting/walking for friends and neighbors. Would be more than happy to take care of your pups :) I’m a college Senior with a light course load this semester and plenty of free time, especially on weekends. My schedule is normally pretty consistent with classes from 12-2pm. Outside of those hours I’m very flexible! I have no pets at my home and have the energy to entertain your pet (no matter how energetic they are). I’m a safety-first kind of person and big on communicating any areas of uncertainty!
“Tara and Logan are amazing! My pup enjoys her time there so much. They run, go to the dog park. She always eats whine she’s there, which means she’s super comfortable. Highly recommend!”
About: From the charming purrs of cats to the wagging tails of dogs, the colorful chirps of birds to the cuddly guinea pigs, and the delightful quacks of ducks, my life has been a joyous menagerie. Each pet brought their unique magic, filling my heart with love and cherished memories. From the tiniest chicks to the graceful fish gliding in their tanks, every creature enriched my life in countless ways. My pet journey has taught me compassion, responsibility, and the beauty of the animal kingdom. I am forever grateful for these wonderful companions who have made my life extraordinary! 🌟🐾💖 Working from the comfort of home has granted me the ultimate gift: precious time. With no commuting and flexible hours, I savor the luxury of ample moments. 🌟🕰️ Whether snuggling with my pets, exploring hobbies, or connecting with loved ones, I cherish every minute. No rush, no stress—just pure contentment. My home is my sanctuary, and time is my cherished companion! 💖🐾 In our abode, safety stands unwavering—providing peace of mind for all. Trust intertwines us, a bond so strong and unyielding. And within this cherished space, a harmonious environment thrives, where love and care nourish every soul. 🏡💕 Embracing these pillars, our home becomes a sanctuary of warmth and unity, where each heart finds solace and joy. Together, we create a haven where safety is protected, trust is celebrated, and the environment flourishes in harmony. 🌟🌱🤗
“Elizabeth and Rodrigo genuinely love Fitzgerald. Their home is loving and they are kind, communicative, and considerate dog lovers. We love visiting them cause Fitzgerald always wags his tail extra hard during drop offs, and comes home happy as can be. Anyone looking for a loving pair to watch their pup would be lucky to have them say yes!”
“Vista had so much fun during daycare with Junho and Boki! Junho was very communicative of how Vista was doing, making sure she had everything she needed to enjoy her days, from her food, to play and outside time. It is clear that he truly loves dogs and I would recommend him to anyone looking for someone with a kind heart to care for their pet.”
“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.”
About: I have had a family dog for over 10 years now and have taken care of her all her life. My own dog now lives in New Hampshire, but I still would love to take care of and play with dogs on a daily basis. I have also watched friend’s, neighbors, and other family members dogs all my life and enjoy every second of it. I am currently on summer break from attending college in New Jersey. I will be in Massachusetts until September and am available every weekday full time for the next 10 weeks to be able to devote my time and care for your dog. My home includes an outdoor deck that leads to a fenced in backyard that is perfect for dogs to be let out and taken outside to use the bathroom or play on the lawn. Also, I have my dogs older bed, toys, food, and treats from before she moved to New Hampshire. My bedroom is also very close to the door leading to the deck, so letting dogs out to use the bathroom in the night is quick and easy. There are stairs leading up the the home but I can easily pick up dogs that may not be able to climb them.
About: I’m a long‑time doodle mom with more than 13 years of hands‑on experience caring for hypoallergenic and low‑shedding dogs. I currently have two doodles — a senior labradoodle and a younger double doodle — and they’ve taught me everything about coat care, temperament, structure, and the unique needs of allergy‑friendly breeds. Why I Specialize in These Dogs My specialization comes directly from my own experience as a doodle owner. When my dogs were in traditional daycare and walking groups, they often came home covered in fur and dander from other breeds. That brought allergens into our home, affected our environment, and caused unnecessary skin irritation and extra grooming for my dogs. I realized that doodles, hypoallergenic, and low‑shedding breeds needed more thoughtful, coat‑compatible care — environments that respect their coats, reduce allergen exposure, and keep them comfortable. That experience shaped everything about how I care for dogs today. My mission is to provide coat‑compatible walks and solo pet‑care services that minimize allergens brought into the home, help dogs thrive through safe, structured socialization, and give families the elevated, allergy‑conscious care they want for their pets. I am open to pet care services for most dogs, just specialize in these breeds :) I offer structured, coat‑compatible pack walks and solo pet‑care services designed specifically for doodles and low‑shedding breeds. My pack walks are small, curated groups of compatible low‑shedding dogs, designed to be calm, structured, and coat‑friendly. My weekday schedule includes mid‑day walks, drop‑ins, and in‑home sitting, all arranged in consistent time blocks that help dogs thrive on routine. Weekdays: • 10:30–11:30 AM — Morning pack walk block • 12:30–1:30 PM — Mid‑day pack walk block • Early morning, late afternoon, and evening availability for drop‑ins, solo walks, or sitting depending on bookings Evenings & Weekends: Available for boarding, in‑home sitting, extended drop‑ins, and specialty care for senior dogs, puppies, and anxious doodles. I provide calm, structured, and coat‑compatible care designed specifically for doodles and low‑shedding breeds. Whether I’m in your home or caring for your dog during walks or drop‑ins, or in my own home, I prioritize safety, cleanliness, and predictable routines. In your home, I follow your dog’s established schedule, feeding and handling preferences, and any grooming or coat‑care routines you rely on. I maintain a clean, low‑distraction environment, avoid exposure to other dogs’ fur or dander, and keep all outings controlled and intentional. My pack walks are small, curated groups of compatible low‑shedding dogs, ensuring calm socialization and a safe, allergy‑conscious experience. I’m highly attentive, communicative, and respectful of your home and your dog’s comfort. My goal is to provide a trustworthy, elevated level of care that keeps your dog safe, relaxed, and understood, while always being mindful of your allergy‑conscious home and the low‑shedding environment your family relies on.
“Hannah was great at communicating and posting pics of Gracie. She took her on walks and Gracie enjoyed her time in Hannah's care. Will definitely reach out again next time we're in the area. :)”
The median cost per day for doggy day care in Winchester is $50
Dog parents share their Rover experiences - Winchester
What a lovely day under thier care. They slowly and carefully integrated my pups into the pack and they had a blast the rest of the day! They had so many treats, walks and lovin’s. My puppy’s silly puppy nature was responded to with ease. She was also very reassuring to my nerves about being new to daycares. I would highly recommend Kayla and will re-book in the future!
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.
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!
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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.
Why Choose Rover?
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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
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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 $36.63 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 2,977 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 2,977 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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