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.
“Cassie is a great dog sitter. She was flexible around my job schedule and also made sure my dog had a great day and even got some exercise! She sent me photos of their activities so I knew my dog was having a good time. I will definitely be using her again!”

“Jessica is the best! My dog loves going to her house during the day and I can tell because she jumps from my truck and runs right to Jessica's door when we arrive. My dog is always very tired at night so I know she's had a good day with lots of play time. Jessica was very accommodating of my long work schedule and is very responsive. I will definitely be using her again.”

“I’m really picky about who takes care of my fur babies, but I couldn’t be happier with this sweet family! They arranged a meet and greet, showed us around their home, and made me feel completely at ease. Throughout the stay, I got regular updates and photos, and it was clear Mochi and Mango were loved and well cared for. I highly recommend them!”

About: I grew up around dogs, starting with my dad raising and training hunting hounds when I was a kid. In my teens, I worked with sled dogs, deepening my understanding of training and care. Since 2013, I’ve been raising and training Chesapeake Bay Retrievers. Specializing in high-anxiety dogs and behavioral issues. I use balanced training methods tailored to each dog’s needs, helping them build confidence and trust. I believe quality pet care should be accessible and affordable, ensuring every dog gets the guidance and attention they deserve. Dogs are part of my everyday life—I run a family-operated kennel on our 9.5-acre farm, where training, exercise, and care are woven into my daily routine. From structured training sessions to supervised playtime and socialization, I ensure each dog gets the attention and guidance they need. I believe quality pet care should be accessible and affordable, making sure every dog has the chance to thrive. Safety is my top priority. Every dog in my care is monitored closely, whether during training sessions, supervised playtime, or rest periods. I have experience working with all breeds, from small companions to large working dogs, and I tailor my approach to each dog's needs. Trust is everything when it comes to your pet’s care. With over 15 years of hands-on experience, I use balanced training methods that build confidence while ensuring a positive, structured environment. I believe quality pet care should be accessible and affordable, making sure every dog has the chance to thrive. When your dog stays with me, they become part of the family.
“Hard to describe, but my dogs are just happy at M&O's house. When I pick them up, they are smiling. I think there's a nice, calm energy in the home, and my dogs love it there. We will be back!”


“Leann was great with our dogs. She is very experienced and obviously loves dogs! We were comfortable and confident after we left our dogs with her. They had a great day and we plan to contact her again in the near future!”

“Absolutely will book my little companion's stay with Tina, again! Tina is a very easy to work with animal caretaker who truly loves what she does. A genuine pack leader! And when it comes to working with my scheduling needs, Tina has always been so understanding and accommodating. For me and my little companion, Tina will always be our first choice! She's been such a pleasure to work with, plus my little beagle just loves her! 😏”

About: I have cared for many dogs over the years, both in my home and in clients’ homes, and I’ve always been told I do a tremendous job. Pet owners trust me because I am attentive, gentle, and fully committed to making every dog feel safe, loved, and comfortable. I work from home, which allows me to give dogs consistent supervision, regular potty breaks, long walks, and plenty of one-on-one attention throughout the day. I naturally connect with animals and take time to understand each dog’s unique personality and needs. What sets me apart is my commitment to: -Creating a calm, loving, and reliable environment -Providing long walks and outdoor time for exercise and enrichment -Giving your dog focused attention and affection -Staying mindful of each dog’s comfort, routine, and emotional needs -Treating every pet like part of the family Your pup will be in safe, caring hands every moment they’re with me. I work from home full-time, so your pet will have lots of attention and company throughout the day. My husband, Gage, and I love animals and provide a peaceful, caring environment with no pets of our own. This allows us to fully focus on your dog’s needs. I’m available for extended periods of time, which means plenty of long walks, outdoor play, and one-on-one interaction. We have a fully fenced yard where your dog can safely explore, play, and get their energy out. Inside, they’ll be treated just like family — loved, supported, and part of our daily routine. All pets in our care stay in our home, where safety, trust, and comfort come first. Gage and I provide a warm, calm, and loving environment with no pets of our own, so your dog gets our full attention and affection. Here’s what you can expect when your pet stays with us: -A clean, peaceful home where your dog can relax and feel secure -A fully fenced yard for safe outdoor play and fresh air -Continuous supervision — I work from home, so they’re rarely alone -Long walks, backyard playtime, and plenty of enrichment -Lots of pets & love Care that adapts to your dog’s routine, comfort level, and personality Your dog will be treated like part of our family — safe, supported, and deeply cared for during their entire stay.
“I had never left our pup Jacco with a sitter we didn't know and a house he didn't know. Alana made the experience very easy. She communicated exceptionally and made me feel at ease leaving Jacco there. He stayed from 8 am to 4 pm while we attended a horse auction (that would have been impossible with a pup in tow in 100 degree heat). He was content with Alana and happy as can be when we picked him up. This was my first experience with Rover and it reminded me of my first experience with AirBnb way back in 2011! Glad to say, they were both good. Highly recommend Alana if you need a sitter in Moses Lake.”
“Niki is awesome! She was flexible when i beeded to pick up later. Crewby was excited everyday to visit. Great environment for dogs. Absolutely would use again and would recommend!”

“Kiera was so fabulous with our 2 year anxious dog! We could tell juice had a good time because when we went to pick her up she was giving Kiera lots of love. Kiera went above and beyond giving juice attention for the entire 8 hours we were gone with 3 walks included! If we ever come back to Leavenworth to go skiing we are going to see if she is available to watch juice again!”

About: I've been around animals my whole life. I have experience with bottle feeding, and helping during labor. I've had experience with oral and eye meds. I've had experience with sick cats. I used to be a caregiver until I got hurt at work. Now, I am currently in the process of getting disability so my schedule is very open. I have a fenced yard and two dogs that your pup can play with. I also have access to a crate to allow your fur baby to have a safe space for themselves!
“Amanda was excellent! She sent pictures throughout the day of my puppy having a good time. I would recommend her caring for your puppy and will utilize her service again when needed!!”

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!
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
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
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.




