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

“Savannah was great! She has an adorable bulldog, Charlie who loved to play with Liily. She has a great setup for the animals and I felt like my pup was very well taken care of. I would definitely recommend Savannah and will be using her for any future needs.”


“Lauren really loves animals and it shows. I’ve never met anyone so kind and caring with their pets. This is the best pet sitting experience I’ve ever had by far and my dog seemed really happy. I’ll be using Lauren exclusively from now on. Thank you so much Lauren 🩷”


“I was a little skeptical about boarding, only because I’ve never done it before. Colter and his pup made my dog, Pilot, feel comfortable. Pilot was able to play with another dog, which he seemed to really enjoy. He was exhausted after his stay, as he’s a little older than the other dog. He was definitely well cared for during his stay. I would book with Colter again.”


About: I grew up on the family farm surrounded by dogs and cats and all kinds of animals - caring for them was part of my life. That lifelong connection led me to volunteer at a local dog and cat shelter where I've gained even more experience with pets of all temperaments and needs. I treat every animal like family and I willl give your pet loving care whether it's for a quick walk or an overnight stay. I have a very flexible schedule so I can fully prioritize pet care. My days naturally revolve around the animals I am caring for and I enjoy creating routine that suits their needs. My home, farm in the woods, is calm and pet friendly space where animals can relax, go for walks or play. In client's home, I'm respectful of their space and routines, I communicate with the owner, send updates and make sure the pet has all my attention.

“Rae and Chris are wonderful with our girl, Pickles. She is a rescue and hadn't been exposed to other dogs in her former home. We really needed to socialize her because we often have guests with dogs at our home. We nervously decided to try day care. Rae and Chris shared their knowledge about dog behavior and reassured us that she would be fine. Within minutes of her first day we got a video of her playing with other dogs! It was amazing, and we feel so happy that we found Rae and Chris. Pickles has been there four times now ... and she LOVES going! We know she's in good hands!”


About: Hello pet parents my name is Octavia (i prefer to go by my middle name)! I HAVE EXPERIENCE WITH MORE THAN JUST DOGS AND CATS SUCH AS CHICKENS AND DUCKS !! I am military and I am able to access base when needed. I am 20 years old and I LOVE animals!! Due to my Army career I live in a lot with my wife, my dog, and my kitten. Taking care of animals is my calling! I have now been in the Army for two years. I joined to further pursue my college education and become a veterinarian in the future. Iam extremely passionate about the care that animals receive. I have volunteered for lots of shelters since i was young to learn all about animals and their needs, so it is my duty to ensure that your fur baby is well taken care of. Being that i worked with a lot of trained animal handlers, I have experience with animals who have many special needs such as diabetes, aids, cancer, seniors, etc. I also have experience with many different ages and breeds of dogs/cats. I previously worked at a groomers and volunteered at a pet shelter. At both establishments I fed the animals, bathed them, played with them, and took them out for restroom breaks. | love to stay active so I go on a daily walk/run and I would love for your pet to accompany me. I have plenty of room in my schedule to spend quality time with your pet. This would include going to the park, play time, and even cuddle time! While you are gone from your sweet fur baby, I will be available for communication 80% of the time. I am more than happy to send updates on how your pet is doing upon request. Anything that makes you and your pets comfortable I am more than happy to do. The less stress there is for you and your fur baby the better! I am here for your needs!! I am extremely excited to be pet sitting again as l did this before I joined the military. I work from 9-5 for the time being until my shift changes but am truly excited to be able to rush home and care for your pets. I will always keep you updated on my schedule being that my hours change every 3 months. I have a dog and a kitten right now and I constantly do research on their diet and behavior and their well being to make sure I am giving them the best possible life that they deserve.


About: I'm especially good with timid animals, and I love making them feel more at ease. I have a soft presence and a lot of patience. I'm good at reading dog language. I'm super responsible, so you can count on me to follow your dog's preferred daily schedule and to send you updates. I work from home, in a neighborhood that's pleasant for dog walking, and we have a fenced backyard. I grew up with small dogs, wanted to be a vet. I've cared for my current doggo for 9 years. I work from home, and my time AWAY from home is flexible. I can definitely be here as your dog is getting used to our home. About your dog's experience in our home: My home office is on the main floor, and I'm aware of all activity in my small-ish house. Your dog can rest on the sofa, futon, rugs, or the big dog bed--or in a kennel if they prefer. I have a fenced yard with room to run. Our friendly 10-year-old, 35-pound boxer mutt, Kiri, enjoys playing with small dogs. But she's not at all pushy. :-) About caring for timid animals: I had a deep, deep bond with a very timid cat, and I just have a super soft spot in my heart for them. I had a shy young kiddo. One of my "day jobs" is a coach for introverted people: I help people honor their introversion, including their need for quiet, calm, and solitude. About my profile photos: I'm the one in the family who takes the photos, so it's nearly impossible to find a photo of ME and Kiri. :-} I include some photos of our house and yard (kids' faces blurred) to give you a sense of our space. Kiri is part of our family. She hangs out in the common spaces with us, and in the backyard. We take her to the dog park or on daily neighborhood walks. The first 3 photos are at dog parks. The rest of the photos show our house and yard.

“Lindsey is so sweet and made my husband and myself feel so at home to leave our puppy with her. This was the first time I’ve left her with anyone and I’m so thrilled it was Lindsey!!”


About: Located just 10 minutes west of the Legends of Kansas City, your fur-baby will get the TLC that you’d provide in your own home. Plenty of attention and room to run! I currently work some evenings and weekends in order to homeschool during the day so we are home often. I will be clear about availability during bookings. My family is fur-baby friendly with 4 goats, a flock of chickens, two sweet puppies, and a cat currently. During bookings my two dogs (one is an outdoor farm dog) and cat will be kept separate to ensure the safety and comfort of all. Any medical, training, attention, and care needs will be accommodated as requested by the owner.

“Marilyn was so kind and generous with taking care of our puppy Obi. He looked like he had an amazing time and I enjoyed seeing how happy he was from the pictures and videos she sent. Would recommend and am happy I found someone who I can trust with my puppy.”


About: I’ve been a dog owner all of my life and always hated it when I had to kennel them for several hours and/or overnights. Always tried to look for people to help out with walks or play time. This is a great resource for those pets in need. Just looking to help your loved one get through those long days alone. I have a flexible job that I spend most of my time at home. It gives me the opportunity to do other things that I need done. I’m available most days. I have a large fenced in backyard and a dog of my own (Calvin). He loves other dogs and loves to have friends over. I’ve been a pet owner my whole life and want nothing but happiness and exercise for all.

About: I've been around and owned large dogs throughout my life, as well as other small and exotic pets. All guests will meet Gracie, our very friendly service-dog-in-training, who loves to make new friends! Every dog I've owned, I've done at least basic household obedience training with. I'm self-employed, work from home, and have a very flexible schedule. Please check the calendar for blocked dates. Gracie and I typically start our day at 8:00AM, but we can receive visitors as early as 7:00. We start the day with breakfast and yard time before the heat comes in. When it starts to cool off in the evening, Gracie and I walk a 3-mile loop from the house to a nearby wooded trail and back. We have plenty of super chewer toys and treats for larger dogs, and a large fenced in back yard with room to run! Depending on weather, the dogs would spend most of the time in the house during the day. All time in the back yard is supervised. Housebroken dogs are allowed on couches and to roam the house. We also have kennels upstairs and downstairs, if needed.

About: I have an immense love for animals and treat my own as if they were my children, giving them endless care, respect, and affection. Their happiness and well-being are my top priorities, and I go above and beyond to ensure they feel safe, loved, and understood. This deep connection extends to every pet I care for, making me an exceptional pet sitter. I am patient, responsible, and attuned to each animal’s unique needs, whether it’s playtime, special diets, or just providing comfort. My dedication and genuine passion for animals make me someone pet owners can trust completely. I am always at home. I do work from home. But that is a few hours per day and my schedule can be adjusted to the needs of any animal. I have a lead setup but all dogs will be taken on multiple walks a day. During bed time they would be with me unless requested by owner to be crated.

About: I’m a huge animal lover . Growing up I had dogs, cats, a ton of turtles, a deer for a short period of time, a squirrel, 2 raccoons, an alligator, and a lot of bunnies. The past 14 years, I had a German Shepherd, named Rocky, whom passed away this past February. I've been animal sitting for my friends and family members for years. From puppies and help with training to elderly animals with needed medical care. Your animal will be well taken care of and apart of our family for the time he/she is here. I'm a stay at home Mom and can devote the majority of my time to pampering and caring for your beloved fur baby. The care for your fur baby will be tailored to fit their needs. I have a big fenced yard and a few acres of land for playing and potty breaks. I have areas around us for hikes or our big neighborhood for walks. Our home is the perfect place for any animal. It's a very loving, nurturing environment where your fur baby will receive a ton of love and affection with many cozy areas for them to relax and play. I can accommodate special needs such as: separation anxiety, medical care, help with potty training if need be, and any preferences you prefer for consistency. I want to make your fur baby's time away from their family as comfortable and enjoyable as possible.

About: I'm grew up life at farm which with many animals. I love pets. There many story to telling. It can't explain.:) just ask me any.:) I work at home and I am always free and take my dog for a walk! I love to walk too which is known we me busy and I make a dogs happy and dogs make me happier! My parent has a big fence back yard. So the dog can play, enjoy, and be free! I always walk through the forest too and I can take the dog with me to hike on leash too in back forest tho!
Loving doggy day care in your neighborhood
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Savannah A.

“Savannah was great! She has an adorable bulldog, Charlie who loved to play with Liily. She has a great setup for the animals and I felt like my pup was very well taken care of. I would definitely recommend Savannah and will be using her for any future needs.”


Annicka H.Star Sitter

“Annicka is an amazing petsitter with our little baby Bentley.”


Lauren K.Star Sitter

“Lauren really loves animals and it shows. I’ve never met anyone so kind and caring with their pets. This is the best pet sitting experience I’ve ever had by far and my dog seemed really happy. I’ll be using Lauren exclusively from now on. Thank you so much Lauren 🩷”


Colter P.

“I was a little skeptical about boarding, only because I’ve never done it before. Colter and his pup made my dog, Pilot, feel comfortable. Pilot was able to play with another dog, which he seemed to really enjoy. He was exhausted after his stay, as he’s a little older than the other dog. He was definitely well cared for during his stay. I would book with Colter again.”




Steve J.
Star Sitter


“Steve is amazing with our old girl and our new rescue pup. I feel so much more comfortable with them with him than with a larger play/day care. 1000% recommend!”


Amber M.

“Amazing communication. Lots of photos. Very sweet. Tired puppy at end of day.”


Petra S.
“Petra is a kind soul and deeply loves dogs (more than people maybe?! haha) She will make sure your dog feels happy, safe, and totally adored. — expect a very happy (and possibly slightly pampered) pup when you get back! She lives on a wonderful dog friendly forested property in the country close to Lawrence. I highly recommend her if you're looking for someone who genuinely cares and goes above and beyond.”


Rae Lynne B.


“Rae and Chris are wonderful with our girl, Pickles. She is a rescue and hadn't been exposed to other dogs in her former home. We really needed to socialize her because we often have guests with dogs at our home. We nervously decided to try day care. Rae and Chris shared their knowledge about dog behavior and reassured us that she would be fine. Within minutes of her first day we got a video of her playing with other dogs! It was amazing, and we feel so happy that we found Rae and Chris. Pickles has been there four times now ... and she LOVES going! We know she's in good hands!”


Tori T.
About: Hello pet parents my name is Octavia (i prefer to go by my middle name)! I HAVE EXPERIENCE WITH MORE THAN JUST DOGS AND CATS SUCH AS CHICKENS AND DUCKS !! I am military and I am able to access base when needed. I am 20 years old and I LOVE animals!! Due to my Army career I live in a lot with my wife, my dog, and my kitten. Taking care of animals is my calling! I have now been in the Army for two years. I joined to further pursue my college education and become a veterinarian in the future. Iam extremely passionate about the care that animals receive. I have volunteered for lots of shelters since i was young to learn all about animals and their needs, so it is my duty to ensure that your fur baby is well taken care of. Being that i worked with a lot of trained animal handlers, I have experience with animals who have many special needs such as diabetes, aids, cancer, seniors, etc. I also have experience with many different ages and breeds of dogs/cats. I previously worked at a groomers and volunteered at a pet shelter. At both establishments I fed the animals, bathed them, played with them, and took them out for restroom breaks. | love to stay active so I go on a daily walk/run and I would love for your pet to accompany me. I have plenty of room in my schedule to spend quality time with your pet. This would include going to the park, play time, and even cuddle time! While you are gone from your sweet fur baby, I will be available for communication 80% of the time. I am more than happy to send updates on how your pet is doing upon request. Anything that makes you and your pets comfortable I am more than happy to do. The less stress there is for you and your fur baby the better! I am here for your needs!! I am extremely excited to be pet sitting again as l did this before I joined the military. I work from 9-5 for the time being until my shift changes but am truly excited to be able to rush home and care for your pets. I will always keep you updated on my schedule being that my hours change every 3 months. I have a dog and a kitten right now and I constantly do research on their diet and behavior and their well being to make sure I am giving them the best possible life that they deserve.




Sondra B.
“I often go with Sandy (and her dog Kiri) to the off-leash dog park. Kiri is always so happy, and clearly enjoys her time out. Sandy is very attentive to Kiri's needs. I see how kind and patient she is, especially with timid dogs. Kiri is well cared for, well trained and gets along with other dogs. I highly recommend Sandy for her excellent dog care.”


Lindsay B.

“Lindsey is so sweet and made my husband and myself feel so at home to leave our puppy with her. This was the first time I’ve left her with anyone and I’m so thrilled it was Lindsey!!”


Rachel J.Star Sitter
About: Located just 10 minutes west of the Legends of Kansas City, your fur-baby will get the TLC that you’d provide in your own home. Plenty of attention and room to run! I currently work some evenings and weekends in order to homeschool during the day so we are home often. I will be clear about availability during bookings. My family is fur-baby friendly with 4 goats, a flock of chickens, two sweet puppies, and a cat currently. During bookings my two dogs (one is an outdoor farm dog) and cat will be kept separate to ensure the safety and comfort of all. Any medical, training, attention, and care needs will be accommodated as requested by the owner.


Catherine R.

“We are very happy with Katie! Sampson just loves her, we think she’s pretty great also. Will definitely be requesting again.”


Marilyn O.Star Sitter

“Marilyn was so kind and generous with taking care of our puppy Obi. He looked like he had an amazing time and I enjoyed seeing how happy he was from the pictures and videos she sent. Would recommend and am happy I found someone who I can trust with my puppy.”


Chelsea L.

“Thank you so much!!!”


Chad C.
About: I’ve been a dog owner all of my life and always hated it when I had to kennel them for several hours and/or overnights. Always tried to look for people to help out with walks or play time. This is a great resource for those pets in need. Just looking to help your loved one get through those long days alone. I have a flexible job that I spend most of my time at home. It gives me the opportunity to do other things that I need done. I’m available most days. I have a large fenced in backyard and a dog of my own (Calvin). He loves other dogs and loves to have friends over. I’ve been a pet owner my whole life and want nothing but happiness and exercise for all.


Stephen M.
“Stephen has multiple years of experience owning pets and taking care of them. He did obedience training on all his dogs he owned and he enjoys training them. He is very patient with fur babies. He loves giving them attention and cuddles. He is also familiar with working dog breeds. I would highly recommend him as a sitter.”


Kasey L.
About: I have an immense love for animals and treat my own as if they were my children, giving them endless care, respect, and affection. Their happiness and well-being are my top priorities, and I go above and beyond to ensure they feel safe, loved, and understood. This deep connection extends to every pet I care for, making me an exceptional pet sitter. I am patient, responsible, and attuned to each animal’s unique needs, whether it’s playtime, special diets, or just providing comfort. My dedication and genuine passion for animals make me someone pet owners can trust completely. I am always at home. I do work from home. But that is a few hours per day and my schedule can be adjusted to the needs of any animal. I have a lead setup but all dogs will be taken on multiple walks a day. During bed time they would be with me unless requested by owner to be crated.


Chelsey E.
“Chelsey took exceptional care of our puppy for two weeks while I was recovering from surgery, and we couldn’t be more grateful! Not only did she potty train our pup—an incredible achievement—but she also showed so much love, patience, and attentiveness throughout. Chelsey consistently ensured our puppy was well-exercised, kept to a routine, and engaged with stimulating playtime. Her regular updates, complete with pictures and videos, kept us at ease, knowing our furry family member was thriving. We would highly recommend Chelsey for any pet-sitting needs—she’s caring, dependable, and truly passionate about animals!”


Tiffany M.
About: I'm grew up life at farm which with many animals. I love pets. There many story to telling. It can't explain.:) just ask me any.:) I work at home and I am always free and take my dog for a walk! I love to walk too which is known we me busy and I make a dogs happy and dogs make me happier! My parent has a big fence back yard. So the dog can play, enjoy, and be free! I always walk through the forest too and I can take the dog with me to hike on leash too in back forest tho!
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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 Aug 2025 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 Aug 2025, 75 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, 88% of Winchester sitters offering doggy day care respond in under an hour.
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 75 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.
