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%.
“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.”
“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.”
“She was very kind and gave me piece of mind regarding my puppies. They were happy to see her in the morning and I'm sure they had a great time with her children. Will be coming back for future references. : )”
“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!”
“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!”
“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!”
About: Im home 24/7 so you need a sitter dog, walker im there 😭 all I do currently is take care of 4 dogs. Always make sure they get their walk so they stay fit, I never over feed, make sure they get their outside play time and nap time I am on it. I currently have plenty of spare time so im very free everyday to go on walks, play take care of a dog whenever needed. Currently do that right now with my own little weiner army all I do all week is take care of dogs. I have 4 small weenies who love to dig and play in the big back yard and i take them on walks every day or every other day depending on their energy. They do mostly love to sleep throughout the whole day and dig.
“Sandra and her home are very welcoming and we appreciated her making the time at a last minute stay. Sandra made sure they had their potty breaks, got exercise, and ate well. We got updates and let us know how the day went”
“Our Bear was in the very best hands! We received messages, pictures and videos throughout the day which we loved! It was comforting to know he was having a blast with the other pups and felt comfortable in their home. Cannot recommend enough!”
“Yoland was so great and so accommodating for our dog who needed to be separated from other dogs. Our trip was due to a family emergency and I felt so much comfort when I dropped my puppy off with Yolanda and her sweet family. I would recommend Yolanda to anyone!”
“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.”
“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!”
“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 ?”
Over 326 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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Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
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2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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The median cost per day for doggy day care in Winchester is $38
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 5 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 Jun 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 Jun 2026, 694 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 5 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 694 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 95% of sitters offer daily exercise, 93% 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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