Doggy Day Care in Winchester
Drop off your dog at your sitter's home in the morning, and pick them up in the evening.
Every sitter passes an enhanced background check. Learn about RoverProtect
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.
About: I have had pets all of my life and cared for newborn kittens to aging cats. I also had a dog and have cared for family and coworkers dogs for up to 30 days while they were traveling. I have two indoor cats and the neighborhood cats show up for dinner often. I am a retired office professional and look forward to caring for your pet any time needed. I am willing to care for your pet with visits each day in your home or comfortable boarding in my home. For care in my home; I have a fenced yard and a large area for pets to play outside. I live on a quiet street for walking dogs. I have a clean quiet space for crating your pet(s) at night time for their safety. For care at your home; I will respect your home, security and the instructions for caring for your pet(s), pawsitively!
About: I've been taking care of animals since I was 5 when I got my first dog, and I've been caring for animals ever since! I've cared for many different species, such as dogs, cats, birds, rabbits, cows, fish, and a couple of reptiles! I'm always looking for new animal friends and would love to meet yours! I'm currently a full time college student, and have two classes a day. I will be available for pet care at all hours other than 10-11am, and 12-1pm during my classes. I have a nice big hallway for your pet if a kennel is needed, and I have great access to a nice, safe walking path, plus a big yard for pets to play. I am very adaptable and can make anything work!
“learned about day care day before I needed it and Casey responded quickly and agreed. She was attentive to my dogs individual needs. She kindly pottied them just before pickup, knowing I would be traveling. I would use her again”
About: I love to make others feel more comfortable about leaving their beloved dog in capable hands while they are away! I work from home so the dogs are not left alone. I love dogs but am not ready to have two in my home full time. Pet sitting helps to keep my dog socialized. I am able to follow a strict routine, give medications and have very flexible drop off and pick up times. My dog is very friendly and I have a fenced in yard for plenty of playtime. I work from home so am here to care for them all day.
About: I have been working at a pets hospital before when I was in China. I have a Rottweiler right now,she is 5 years old. I play with her after I got home. I can take care of your pets on Monday-Friday at 5:00pm-8:00pm,Saturday and Sunday are all day long available,holidays are also all day long available.No overnight! I have a big yard and fence,my dog is very independent,I always play with my dog,she loves the ball and rope.we often play tug of war.
About: I became a dog mama long before I became a human mama. I know how important trust is when it comes to your pets, so I prioritize clear communication, regular updates, and genuine compassion, so you can relax knowing your furry family member is in loving, capable hands. 🐾 I currently stay at home with my boys so I am available to give lots of love and attention to your fur babies while I do the same to my own! I have a large fenced in backyard, a quiet neighborhood for walks, 2 toddler boys who will help with lots of playtime, and a small dog who loves company!
“Samantha and her husband did a great job while Becket was at their house today in doggy daycare. She kept us updated with pictures throughout the day and gave us a summary of his day at the end (eating, potty habits, etc) . Our dog loved playing i their big backyard with their dog, Marci. Just what we wanted was a worn out puppy at the end of the day! He enjoyed it so much! We have already booked another date.”
About: I've taken care of dogs since I was kid. To me they are like family and should be treated with love. I have 3 of my own that I've had since they were puppies. I'm currently working part time so I'm using my extra time to help others with their fur babies. I'm home most of the time so I can give them extra attention. My back yard is fenced in. I have dog crates available if they need it. Tons of toys and treats too. Clean and bug free home.
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
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
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per day for doggy day care in Winchester is $25
Why Choose Rover?
Cashless payments
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.
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 $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 Jun 2026, 17 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.
Typically, sitters offering doggy day care on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
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 17 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.
Connect anywhere with the Rover app
