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. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Kristen has been caring for my dog consistently for over a month now and is fantastic! My dog loved going to her house and playing with her dogs Whiskey and Cooper. Kristen was exceptional about keeping me updated on how he was doing and uploading pictures. I can’t recommend her enough!”

“Jody has been professional, courteous and trustworthy. She is flexible and convenient. I am very thankful that she was able to care for my fur baby Enzo. We appreciate you so much! Glad that Enzo got to play with River! We will definitely not hesitate to have you care for Enzo again when we come back! THANK YOU!”

About: My wife and I have taken care of family and friends loving best friends together for almost 5 years. Individually, we've taken care of them much much longer. Our names are Sydney and Savannah. We both started out with family and friends pets. Around the age of 10. Until eventually, we grew our own customers and met new families! You can count on us to give your loved one the utmost care and of course, plenty of kisses, they deserve. If your dog wants to run, we'll run. If they wanna stay inside and play with toys, Our 2 babies would love to join and play along. My dogs are my children, I'll make sure to love yours like my own. If you're looking for someone trustworthy enough for your furry family, you found us. We can work with tight schedules and we will always do our best to make life just a little easier. We are also able to take care of special needs dogs. Contact us today if you have any questions, we can schedule a meet and greet today! My wife and I enjoy our time with our family & fur babies. Whenever your baby is here, they’re family! We always have someone home☀️ We full time RV live so we have a lot of activities we can do on a daily basis! Inside isn’t really our thing. ☀️
About: I've been a veterinary nurse for over 10 years. I'm experienced in all facets of animal care and specialize in pets with medical needs and seniors! I work per diem in veterinary medicine. My schedule has a lot of flexibility! I like to vary my weeks between the two. Spending time with others pets and helping animals in clinic keeps me happy and makes me proud! In my home, pets will be treated as my own. I do not require kennels or cages if the pet isn't used to them. I invite them to be as comfortable as possible! I give them my undivided attention, and depending on the activity needs of the dog, take them on plenty of walks and adventures! Cats hold a special place in my heart and are always welcome in my home. ❤️
About: I’ve owned dogs for my entire life. I am currently a breeder. Loving and caring for dogs is my passion and I treat every dog like they are part of my family. I am a retired teacher who spends my days loving and caring for my fur babies. Pet care is a natural part of my daily routine and I am blessed to be able to give them the attention, playtime, and comfort they deserve. I offer loving pet care through both in-home and convenient drop-in visits. With years of experience raising cats and dogs, I provide a safe, comfortable, and affectionate environment, making sure your furry family members are happy and well cared for while you are away.
About: I've always been a dog person. I take care all of my family and friends dogs when they leave town. Familiar with dog training and nutrition. I work remotely and have freedom to walk, feed, and pay attention to your dogs as needed. I love dogs and enjoy helping them feel at ease. Pets can cuddle on ample dog beds and couches. I lost my dog a few years back and I just kept all her stuff set up. Your dogs will have free reign of backyard and house as long as they are well behaved.
“Quill had a blast with Christina! He’s usually very nervous but Christina took the time to make him feel comfortable and that’s the best thing you can ask for with someone watching your dog. I would 100% book with her again.”

About: I have fostered over 250 amazing dogs, mostly seniors and special needs, so I have experience with most any medical or behavioral care. I have had dogs ages newborn to 16+ in my care, so I have experience with all the life stages. I have experience training dogs of all sizes, from 5 pounds to 150 pounds. I believe that my calming presence around animals set me apart to earn their trust. I am home nearly 24/7 and spend most of that with my personal pets or farm animals, so being with your pet would just be added into my routine. I have a fenced in yard. I have fostered over 250 dogs. While my small inside dogs are very friendly, I am comfortable with separating if needed using crates or gates. My inside dogs are 10 pounds and under. Pets have access to all areas of my home, with supervision.

About: I have a big heart for taking care of dogs of all shapes and sizes. Even special needs dogs. (I have one that has seizures). If your dog needs a little training I will be happy to help. I am good with grooming. Prayers forbid I should need to use it but i am good with first aid too. I once was a CNA and was trained in CPR too. I let the licence go because I realized I wanted take care of animals, mostly dogs, not humans. I want to follow my heart and feel happy with my life. Dogs are special creatures and should be treated as such. I will even do vet trips for you if needed. I am available almost every day all day except the rare doctor appointment days.
About: My fur babies mean a lot to me and I know anxiety that comes with leaving your animals in someone else’s hands, we have used Rover in the past with great success, I want to ease the minds of clients by meeting their babies first and really getting a feel for their routine and try to make both owner and pet feel comfortable with me. I am a stay at home dad home schooling my youngest daughter. I have a lot of free time to care for your animals. I’m here to take the stress away when thinking about who will watch your animals for your next trip. I have a large fenced in yard. I have several crates for those dogs that are crate trained. Drop in appointments are welcomed because dogs are most comfortable at home.
“Nicole is amazing. I felt really safe leaving my puppy with her. She goes over the top to make sure she meets the needs of your pup and you! I highly recommend her caring for your pets. Trustworthy, honest, caring, patient, kind and more! You won't regret choosing her.”

Over 4 pet parents in Winchester have booked doggy day care
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The median cost per day for doggy day care in Winchester is $25
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It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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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 Jan 2026 was about $25 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 Jan 2026, 23 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, 91% of Winchester sitters offering doggy day care respond in under an hour.
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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 23 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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.


