Doggy Day Care in Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
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Top rated Winchester doggy day care sitters
Prices are estimates per day for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Leyna was so communicative before, during, and after Finn’s stay. She was happy to answer questions prior to booking and sent lots of photos throughout the day. Finn had a great time playing with her dog and I can already tell he’s going to pass out when we get home. If we have any dog sitting needs in the future we will definitely reach out to Leyna!”
“Angela was an awesome sitter for Remy and took great care of him over two days. She was flexible with my schedule and communicated throughout the day with updates and pictures. Remy got excited when we pulled up to her house on the second day. He knew he was in for a fun day! I would definitely recommend her to anyone looking for a reliable and caring dog sitter.”
“I couldn't be more pleased with Skilar's impeccable care of my dog during the week I needed help. Right from the start, she showed a lot of affection, attention and responsibility, which put me completely at ease. My dog came home happy, healthy and clearly well cared for. The attention to detail, such as maintaining the feeding and walking routine, was incredible, and I even received daily updates with photos and videos, which made all the difference. I would recommend Skilar with my eyes closed to anyone looking for someone they can trust to look after their pets!”
“Fernanda was great! It was our first time using Rover and she helped us navigate it. We felt at ease leaving our puppy Anto with her. She was very communicative and sent us pictures with updates. Drop-off and pick-up were easy. We will definitely book her again!”
“My Frenchie Camille loves her stays with Oana, Oliver and friends. So accommodating and kind! So happy we found them! Thank you for loving Camille when we’re gone at work our vacationing :)”
“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”
“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!”
About: What sets me apart is the patience and care I bring to every pet I look after. I’ve trained playful puppies through their wiggly, curious stages and also cared for sweet senior cats who need a gentler touch. Since I work from home, I can give your pet plenty of attention, love, and supervision throughout the day and make sure they always feel safe, happy, and cared for like family. Pet care is really the heart of my daily routine, it’s what I do full-time and absolutely love! My days start and end with walks, playtime, and cuddle sessions, and I plan my schedule around the pets I’m caring for. Whether it’s an exploratory trip in the morning , mid-day ball chasing games, or winding down with dog-friendly TV shows in the evening, every part of my day includes something fun and furry. In my home, pets have plenty of room to feel comfortable in my spacious townhouse and can play safely in the big fenced yard. They’ll also have a built-in buddy, my friendly 6-year-old French Bulldog who loves company. I make sure visiting pets get lots of playtime, walks, and cuddles, while keeping their routines consistent so they feel right at home.
“I cannot recommend Marie enough! Nova fell in love with her instantly and warmed up to her so quickly. Marie has such great energy, and you can tell she’s a genuinely kind and caring person. It’s clear she took excellent care of Nova, who had the best time with her. We’ll definitely be booking with Marie again and 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.”
“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.”
About: I’ve had a dog since I was 8 years old and have been dog sitting for friends and family since I was 10. I currently have a friendly, 4 year old golden retriever, named Harley, who love playing with other dogs. I plan my days and weekends around getting Harley plenty of exercise and mental stimulation and if I am watching your dog you can expect the same! I currently work from home with my dog Harley and we would be thrilled to add another friend to our group. I never leave Harley home alone for more than 4 hours and she gets long walks, training practice and playtime every day. I live in an apartment in Medford. Our location is near many great walking trails along the mystic river and we have access to two nearby dog parks (one is private for the building so the dog traffic is very low). Dogs are allowed on furniture here. Harley will play with dogs who are interested, but is otherwise happy to just hang out with lower energy companions.
“Luci and her family were absolutely incredible for our pup! From the moment I reached out, she was incredibly responsive, professional, and accommodating. During her time with them, she was treated like family! Luci sent regular updates, including adorable pictures and videos, which made me feel so at ease. This was my first time leaving my pup alone and she was so happy every day she was there. I highly recommend!”
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.
“Sara and Ari were fantastic!! They took the time to offer a meet up to answer any of our questions and to make sure our two pups would get along. Day of, Benji had so much fun playing with Bond (their 9 year old pup), he didn't want to leave!! We also got photo and video updates throughout the day. It was great to see Benji be loved and taken such good care of! We'll be sure to have Sara, Ari, and Bond watch Benji again!”
Over 38 pet parents in Winchester have booked doggy day care
Winchester dog parents share their Rover experiences
Our dog Toaster had a really great time spending a day at Surendra’s place. Surendra’s communication is outstanding. He responded pretty quickly to my every message. He also provided constant updates on Toaster by sending photos and videos. Toaster came home happy and tired and crashed into his bed almost immediately. I appreciate their professionalism and reliability and would definitely recommend them. I myself will definitely book with them again in the future.
Luci and her family are incredible! My baby boy, Chandler, is literally a Velcro-dog... He doesn't leave my side, 20+ hours a day for 3+ years. When needing to leave him to go out of state, I was anxious, he was anxious, my husband, Dad, and neighbors were anxious! Luci, et al, were wonderful! Providing updates, pictures, and helping ease my anxiety any time I reached out. So very thankful to be able to leave my little guy with these caring, loving people. To know he's being cared for so attentively, while I need to focus on other things, has given me great peace of mind. 🫶
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!
Elizabeth and Neil are so attentive to my Honey bun! They are true animal lovers and provide the best play space! So thankful to have people I can trust when I’m at work! Small play groups with repeat clients creates such a fun group of pups. Honeys new bestie is Zoey ❤️
We had a wonderful experience with Carol for Finley’s first-ever daycare through Rover. As a first-time daycare user, we were a bit nervous, but Carol made the entire process smooth and reassuring. She was extremely responsive both before and during Finley’s stay, answering all our questions and keeping us updated with photo and video of him playing and settling in. Carol’s calm and caring approach helped him feel comfortable and safe. We’re so glad we found her and will definitely be booking with her again. Highly recommend Carol to anyone looking for a reliable, communicative, and genuinely caring sitter!
Heather was FANTASTIC! I was easily able to tell she truly cared about Basil. She was great at providing updates and pictures. This was my first time using rover and she made me feel completely at ease prior to watching Basil and it was nothing short of my high expectations!
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!!
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The median cost per day for doggy day care in Winchester is $45
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Sitters in Winchester average 3 repeat doggy day care clients
Doggy Day Care FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winchester on Rover as of Nov 2025 was about $45 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Nov 2025, 2,822 sitters provided doggy day care in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 85% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 15 years of experience. Sitters offering doggy day care with repeat customers have an average of 3 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winchester.
Winchester doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winchester sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:
- Puppies and high-energy dogs
- Dogs with special needs, including seniors
- Pet parents who work long hours
- Dogs with separation anxiety
There are 2,822 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 94% of sitters offer daily exercise, 94% offer medication administration, and 89% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your doggy day care sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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