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%.
“Jennifer is wonderful! She’s taken my dogs for daycare a few times now and my dogs love her. She’s been super flexible with my schedule, very communicative, sends updates and videos throughout the day, and my pups are always happy with her. Thank you Jennifer!”
“Tashia was such a great caretaker for our beagle! Our beagle had such a fun time playing with the other dogs - Tashia sent photos and video! You can tell Tashia loves animals and cares about your pet…..we will book her again.”
“Tammi was heaven sent. We have had problems getting a sitter for our one year old puppy until we met her. Her facilities for boarding and daycare are perfect for our energetic puppy. Her dogs are friendly and accepting and Tammi is wonderful with them all. Tammi is a dedicated and considerate person and will provide loving care for your animals.”
“They were awesome with being able to accomadate me so last minute! They provided me with pictures and updates and I know he was in good hands. Levi was so happy to stay here and I definitely hope to get their help again soon!”
“We were very pleased with care provided. Frank, Saleha and their children were very welcoming and both Maya and Chiquita seem happy to be there. In particular, Chiquita, our 15 yr old did not show any anxiety or stress, on the contrary and Maya seem to enjoy the company. We would definitely feel comfortable leaving the girls and recommend for others. Thank you!”
“Paulena took wonderful care of our dog! He was always excited to see her and had so much fun playing with the other dogs. She was flexible, easy to work with, and kept us updated with great communication. We’d absolutely recommend her to anyone looking for a caring and reliable pet sitter!”
About: I treat every pet like my own with genuine love, patience, and attentive care. After saying goodbye to my last fur baby, I truly miss having animals in my daily life and would be honored to be a loving " pet grandma" to yours. From peaceful walks around the lake to maintaining feeding schedules, playtime, quiet relaxation, and plenty of cuddle time. I provide a safe, nurturing, and protective environment. One-on-one care just like home. No kennels or cages. I’m currently retired and home most of the time. I have no pets or children but love both. My availability is very open. I miss my dogs so much. I have a spacious home with a great, fenced-in backyard. Lots of grass and shade. I live in a safe, family-oriented neighborhood with lots of walking trails and a lake.
“Had an emergency needed a sitter and she responded within minutes. She took care of my puppy for about 3 1/2 hours my puppy looked happy when we got him back gave me an update on how he was doing while sh had him really nice and assured me he was in good hand! Thank you Chanelle ?”
“Once again love taking our Cash over to Alyx he always had so much fun with her and her doggies. Cash definitely gets his dog times and I know he is well taken care of . I give Alyx 10 stars 🌟”
“Serena was great, she sent alot of photos and updates of our pup. Our baby felt safe and had so much fun playing with her dog. I would definitely use her again when in the area!”
About: I've been taking care of my dogs for 7 years taking them on daily walks and weekly park visits for their enjoyment. I have taken great care of many breeds of dogs to help friends when out of city. I love dogs and would love to help with their walks I'm available at any time all week, I can schedule your pet either morning or afternoon and weekends. I work from home so I'll be available at any time, any day of the week Pets will stay inside most of the time and going outside for potty but supervised all the time to make sure they are safe always
“Fiona was awesome! Marty was happy (and tired!) when we picked him up. You could tell he was treated as if he was in his own home. I received a couple of pics and updates throughout his stay which was appreciated. Marty will definitely be back to see his doggy sitter! Thanks again Fiona!”
“OMG!!!! Demelia was amazing with our dog from day one till we picked him up. She was very personable, love what she does, & kept us informed throughout. She sent us live videos daily of our dog having his walks, playing time with her dog “Moon” who’s also amazing, & cuddle relaxing time. We couldn’t have asked for a better sitter. We would definitely book her again & again. Thank you so much for loving on our dog like he was your own.”
“Yolanda is officially apart of our family. She has taken outstanding care of all my dogs and I refuse to let anyone else take care of our pups. We utilize her on the norm, she does our nail clippings and baths as well! My dogs come back pooped, clean and happy! The moment we pull up to her house, they are already out the door sitting in front of her front door!”
“Nicole is absolutely amazing! She was so kind, understanding and accommodating. She provided plenty of photo and video updates throughout the day and I loved seeing how happy my baby was while I was away. Our puppy Stella had an absolute blast playing with Nicole’s doggo Sunshine each day during her stay! She finally made a new friend who can rival her energy. Each morning she was so excited for drop-off with her new friends and each evening she came home happy and thoroughly worn out, which is really saying something for our little furry ball of energy! Stella already can’t wait for her next visit with Nicole and Sunshine. Nicole is a quality, caring sitter who I cannot recommend enough!”
Over 323 pet parents in Winchester have booked doggy day care
Winchester dog parents share their Rover experiences
Tammi was heaven sent. We have had problems getting a sitter for our one year old puppy until we met her. Her facilities for boarding and daycare are perfect for our energetic puppy. Her dogs are friendly and accepting and Tammi is wonderful with them all. Tammi is a dedicated and considerate person and will provide loving care for your animals.
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The median cost per day for doggy day care in Winchester is $38
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Sitters in Winchester average 4 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 May 2026 was about $38 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 May 2026, 685 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, 90% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 17 years of experience. Sitters offering doggy day care with repeat customers have an average of 4 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 685 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 91% 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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