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
“Jasmine was fantastic with Maple! She watched her at her apartment for a few days while I was busy with work. She gave great updates and Maple was always super happy to see her in the morning.”
“Oana and Oliver are wonderful dog sitters!! They are kind, easy going, and always send the best pictures! We had an extenuating circumstance with our trip and they were completely accommodating and understanding. I highly recommend them for all doggy daycare and sitting needs!!”
“Jeongeun was absolutely wonderful with my 12-week-old puppy, Chowder. I was originally nervous about finding a sitter since puppies can be a handful, but Jeongeun went above and beyond. She sent photo updates, which really helped ease my mind and made it clear Chowder was in great hands. She was super communicative, made sure Chowder got plenty of walks and playtime, and treated her with so much care. I’d absolutely book with her again!”
“Elizabeth and Neil are the perfect sitters :-) Everything went beyond expected for our rescue puppy for her first time without us. Apparently, she had a marvelous time running in the garden chasing her companions or just relaxing on the rug. Elizabeth and Neil sent us regular video or photo updates. We will definitively put our dog in their care again in the future.”
About: I do like long walk's in parks and ponds with small beach access for pets to get to the water. That also seems to be the most liked experience for the dogs, making it a memorable experience. I’m currently working from home with plenty of time to care for pets and walk them. On the weekends I’m hoping for their company on more exploratory trips. I have fenced yard with green grass and garden. Also a deck where the pets can enjoy the garden and threes. At any time of the day they can go out and there will be plenty of shade to be under.
About: Animal lover with over 7+ years of experience working with cats and dogs. As a mother of one (my dog), I take pet sitting very seriously. I have an eight year Shiba Inu whom I love with all of my heart. As a pet parent myself, I know the importance of hiring a professional and attentive pet sitter during important events, both planned and unplanned. I initially started Rover in undergrad hoping to fill my time but have continued using the app because of my love for animals! As a caring, attentive, and patient individual, I believe in providing the best care for your pets. My goal is to provide gentle care and give the best cuddles to your pet(s) while you’re away. I work mostly from home and can provide flexible care for your little one(s)! I am fully available on weekends and holidays if I am not already booked! Clients love that I send lots of pictures and videos every visit! At time time, I am unable to accept reoccurring services. I work mostly remote and usually start my day early. I aim to mimic your daily schedule so your little one doesn’t feel overwhelmed or anxious. I’m flexible and can go on walks many times a day! I stay pretty active and generally take my own dog out for 4/5 walks per day. I enjoy long walks and exploring new neighborhoods! I enjoy reading, learning new hobbies, and occasionally bake.
“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.”
“Leon is a fantastic host for doggy daycare! I requested a last-minute booking for daycare (less than 1 day in advance) and Leon replied quickly that he could watch our dog. We even picked her up a little late and he was very accommodating. Our dog has anxiety but she did very well, going on a walk with him and eating all of her food. I fully recommend Leon for doggy daycare services!”
About: I have been a pet owner all my life. My love for all animals are treated like a family member by me.If your pet can sit on my couch and snuggle in my bed with me then he’s /she is the right match. Multiple dogs are welcomed. More the merrier. I have the patience for your Senior dog because I am home full-time. I am retired from the medical field so I am available to play ,watch , walk and give that extra attention to your fur baby. This is my full - time job. I have a beautiful yard fenced in. I have water sprinklers, doggy pool for the summer. I have a beautiful shaded porch. Lots of room to run around indoors and outside. I am extremely loving your pet as it was my own.
“Ben was super flexible with our schedule and very quick to respond / help us out. The whole family jumped in to keep our pup well engaged all day, and we sincerely appreciate their support. Will absolutely reach out again when in need!”
“Isabel did an excellent job caring for my pup. She took him on four walks throughout the day and played with him indoors as well. He looked very comfortable and at ease in the pictures and videos she shared, and he’s usually a fairly anxious dog when it comes to new people and places. I have no prior relationship with Isabel; nor did she ask me to review her. Just doing this to point out that she’s a great sitter, and you should hit book!”
“Yesika was so great! We can tell our puppy was very active and busy all day because she came back exhausted. It was a great opportunity to let Io meet other dogs and humans, and Yesika was very accommodating in every way.”
About: I have had pets my entire life since I was a child and I absolutely adore them! I consider myself a highly sensitive person and that helps me stay attuned both to humans and pets! I have a flexible work from home job and because of that pet sitting fits smoothly with my daily and weekly routine. I can adjust as needed! I feed them on time, play with them during play hours and make sure that they feel safe and take care of. I would make sure to read the pet body language and make sure to give them enough space when they’re shy or not ready to interact!
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.
About: I have many years of experience working with dogs and cats . I have experience training and grooming dogs. We offer senior care and long term care in a comfortable , fun and loving space for your loved ones . I care for dogs in my home every day. Sometimes I have only one dog in my care, I’m open to housing more than one pet. Please reach out if you have any questions. In my care, your pet will be cared for lovingly. I take pride in my work and care for all animals. I am very patient, understanding and open to your ideas .
Loving doggy day care in your neighborhood
Search Results
Jasmine T.
“Jasmine was fantastic with Maple! She watched her at her apartment for a few days while I was busy with work. She gave great updates and Maple was always super happy to see her in the morning.”
Oana & Oliver B.
Star Sitter
“Oana and Oliver are wonderful dog sitters!! They are kind, easy going, and always send the best pictures! We had an extenuating circumstance with our trip and they were completely accommodating and understanding. I highly recommend them for all doggy daycare and sitting needs!!”
Leyna C.Star Sitter
“Leyna was amazing and I could tell Maverick was genuinely happy to be spend time there! Would highly recommend!”
Betsy C.Star Sitter
“Betsy was wonderful and very patient with my dog Louis who can get separation anxiety. Louis had a great time at Betsy’s and came home happy and very tired!”
Jeongeun J.Star Sitter
“Jeongeun was absolutely wonderful with my 12-week-old puppy, Chowder. I was originally nervous about finding a sitter since puppies can be a handful, but Jeongeun went above and beyond. She sent photo updates, which really helped ease my mind and made it clear Chowder was in great hands. She was super communicative, made sure Chowder got plenty of walks and playtime, and treated her with so much care. I’d absolutely book with her again!”
Elizabeth and Neil C.Star Sitter
“Elizabeth and Neil are the perfect sitters :-) Everything went beyond expected for our rescue puppy for her first time without us. Apparently, she had a marvelous time running in the garden chasing her companions or just relaxing on the rug. Elizabeth and Neil sent us regular video or photo updates. We will definitively put our dog in their care again in the future.”
Lilia M.
About: I do like long walk's in parks and ponds with small beach access for pets to get to the water. That also seems to be the most liked experience for the dogs, making it a memorable experience. I’m currently working from home with plenty of time to care for pets and walk them. On the weekends I’m hoping for their company on more exploratory trips. I have fenced yard with green grass and garden. Also a deck where the pets can enjoy the garden and threes. At any time of the day they can go out and there will be plenty of shade to be under.
Amanda Leigh I.
“Amanda was so great with Bao! She updated me with pictures and messages. Bao was so comfortable with Amanda and her own sausage dog. 1000% recommend 🥰🐶”
May H.Star Sitter
“May is one of the most hardworking, loving and caring handlers out there. She has multiple experiences with handling all types of dogs. May treats each dog as if they were her own. May loves dogs and they aren’t just animals to her, they’re companions. Her passion for dog care is above and beyond others. I would trust her with my dog 100% and would not have any worries with her taking care of them.”
Cheuck L.Star Sitter
“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.”
Luci P.Star Sitter
“Luci and her family took such a great care of our pup. I received many updates with photos and videos during the day. Winnie looked happy when I picked him up!”
Christopher & Nicole G.
“Thank you for a wonderful month of ‘Elsie’ care. Enjoy hour holiday. Christopher & Nichole are excellent. I was very fortunate they were up for a puppy!”
Leon A.
“Leon is a fantastic host for doggy daycare! I requested a last-minute booking for daycare (less than 1 day in advance) and Leon replied quickly that he could watch our dog. We even picked her up a little late and he was very accommodating. Our dog has anxiety but she did very well, going on a walk with him and eating all of her food. I fully recommend Leon for doggy daycare services!”
Maryann G.Star Sitter
“Maryann is such a great care taker of my 12 year old high anxiety dog that needs a lot of attention and she did everything right with him and he loves going to her home and on adventures. I trust only a few people with my pets and she is def one of them ! 10/10 experience. Such a relief being able to put my trust in someone else with my love one.”
Ben M.Star Sitter
“Ben was super flexible with our schedule and very quick to respond / help us out. The whole family jumped in to keep our pup well engaged all day, and we sincerely appreciate their support. Will absolutely reach out again when in need!”
Isabel F.
“Isabel did an excellent job caring for my pup. She took him on four walks throughout the day and played with him indoors as well. He looked very comfortable and at ease in the pictures and videos she shared, and he’s usually a fairly anxious dog when it comes to new people and places. I have no prior relationship with Isabel; nor did she ask me to review her. Just doing this to point out that she’s a great sitter, and you should hit book!”
Yesika S.
“Yesika was so great! We can tell our puppy was very active and busy all day because she came back exhausted. It was a great opportunity to let Io meet other dogs and humans, and Yesika was very accommodating in every way.”
Noura T.
“Nora has been a regular cat sitter for our cat, and my cat adores her. She is sweet, attentive and communicative. I recommend her to other rovers!”
marilyn g.
“Hi, I am a dog and cat Mom, I have had Marilyn watch all my pets for many years. What I think sets Marilyn apart from other sitters I have had is her experience as a veterinary technician. She has been such a huge help with some of my medically complicated or geriatric pets over the years! She goes the extra mile to make sure they get the care they need. I’m so thankful we have her!”
Tiffany R.
About: I have many years of experience working with dogs and cats . I have experience training and grooming dogs. We offer senior care and long term care in a comfortable , fun and loving space for your loved ones . I care for dogs in my home every day. Sometimes I have only one dog in my care, I’m open to housing more than one pet. Please reach out if you have any questions. In my care, your pet will be cared for lovingly. I take pride in my work and care for all animals. I am very patient, understanding and open to your ideas .
Over 31 pet parents in Winchester have booked doggy day care
Winchester dog parents share their Rover experiences
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!!
Oana and Oliver are a great choice for taking care of your pup. For the last few years our goldendoodle has enjoyed both day and overnight care and has never been disappointed. As the pup parents we always felt our dog was well cared for and got lots of attention and great exercise. Strongly recommend!
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
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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 Aug 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 Aug 2025, 2,717 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, 87% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 16 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 2,717 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 93% of sitters offer daily exercise, 94% offer medication administration, and 88% 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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