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

About: I have always had at least one dog of my own. I don't know how to live without them. I started a dog sitting/boarding business in Idaho and ran that while working in a pet supply store at the same time. We had the best of times! I am currently not working, but seeking only part-time work, so I have plenty of time on my hands to love up on ALL the dogs! Walking, throwing the ball, tug of war- you name it! I'll even be the pooper scooper at your home if necessary. I have a big fenced and secure grassy backyard. I also have two friendly dogs, one big and one small. They are BEST friends and always welcome company both human and canine. We have many dog beds and toys, as well. I also have room to crate your dog if that is what you and your pet are comfortable with.

“What an amazing app with opportunities to find animal lovers like Crystal who was quick to respond, sent us updates and flexible with our schedule. We drove over 8 hours out of town for a wedding, and not wanting to leave our dog in an AirBnB for the entire hectic day, leaving him with Crystal was the best decision! We could tell by photos he was well loved and enjoyed so much his time with them!! Thank you app creators and everyone willing to of care for pets when needed!!”


About: I’ve been the go-to dog sitter for friends over the past 4 years, and I’ve had my own furry best friend for 10! As a pet-loving photographer, I’ve worked with animals in studio shoots and love teaching basic commands. I’m not a current pup parent—so I’m soaking up every wag, cuddle, and tail thump I can! I work from home and have plenty of time (and love!) to give your pup the attention they deserve. Whether it’s weekday walks, weekend cuddles, or just keeping them company, I’m here and happy to help. I know how important it is to feel your dog is in good hands—and I’ve got two ready! Your pup’s safety and happiness are my top priorities. I have a secure fenced yard for playtime and can provide as many daily walks as needed. Since I work from home, your dog won’t be left alone for long. I’m also happy to show you my home and do a trial visit or trial hour, so you feel completely comfortable leaving your loved one with me.

About: I have been an animal lover all my life and have had animals of all kinds for many many years! I love to dog sit and love on fur babies as much as possible! I am currently retired and home most of the time. If I leave home it’s only for a short errand and then I return home promptly. I have a privacy fenced yard and 2 small dogs for playmates. I have extra pet beds if needed. I just want your babies to feel comfortable and Loved on because I understand how much they miss their families. 💜💜💜

About: I’ve been caring for pets since I was 10 years old, starting with family cats and dogs, and quickly becoming the go-to sitter for friends and neighbors. My wife and I began offering pet walking and sitting services in our local community when we were 16, and she’s now a certified pet groomer — I’ve assisted her with bathing, brushing, and keeping pets calm during grooming sessions. Over the years, I’ve cared for animals of all temperaments, from shy rescues to high-energy puppies and confident cats. I treat every pet as if they were my own, giving them patience, attention, and lots of love while making sure their daily routines are followed exactly. My schedule is completely open, which means I can give your pets as much time and attention as they need. Whether it’s early mornings, late nights, weekends, or last-minute requests, I’m available and ready to help. Your pet’s care will always be my top priority. I live in a small, quiet apartment with two sweet resident cats (no yard). My home is tidy and cat-safe—screens secured and doors monitored—with plenty of enrichment and calm spaces. I scoop litter twice daily, refresh water often, and follow exact feeding/medication instructions. For dogs, I provide care in your home or on walks only. I use gentle, patient handling and share frequent photo updates so you always know your pet is safe.

About: Hi! My passion has always been to work with animals. I started Pet sitting for my neighbor at 16. I was a Veterinary Assistant at 18. I was accepted into TCC's Vet Tech program but was encouraged to focus on my baby. I have always wanted to own my own Pet- Sitting business and now at 25 years old with 9 years of experience in pet-sitting, plus having many fur babies of my own throughout the years, I want to pursue my dream! I can't wait to meet you and your furry family! I am free and at home most of the time. The only times I am not available are 10 am to noon every Monday, Tuesday, Friday, and Saturday. I also go to church every Sunday from 10 am to noon. Other than those times, I am free to pet sit, dog walk, and board at any time. I have two senior medium-sized dogs (a boy and a girl) and one small female cat. All animals are fixed, and up to date on shots. The cat is not declawed. I give my female dog an insulin shot twice a day. I am capable of administering medication. Animals are allowed on the furniture. I also have a Five year old little boy which limits me to only boarding in my home. I can take care of animals in their homes as long as I am not required to spend the night in the home, I will visit as often as needed.

“We really appreciated Logan's professionalism and flexibility and he was very good with our dogs. My parents dog is a particularly nervous type and Logan seemed to know just how to make her comfortable. Dogs came home worn out after playing most of the day. Logan also was very flexible and accommodating with scheduling which we really appreciated. Overall, great experience.”


About: Hi! I'm Sarrah – part-time human, full-time pet enthusiast. Although I’m new to professional dog sitting, I’ve spent years caring for my own pets and fostering dogs and cats through local rescue organizations. I understand how important it is to find someone you trust to care for your furry family members, and I treat every pet like one of my own—with love, patience, and attention to their unique needs. Whether your dog loves long walks, cuddles on the couch, or just needs a calm, reliable presence while you're away, I'm here to help. I’m comfortable with dogs of all sizes and temperaments and always prioritize safety, communication, and making your pet feel at home. Let’s chat—I’d love to meet you and your fur baby! Pet care is already part of my routine from having my own pets and fostering. I'm available afternoons and weekends during the summer and happy to provide care that's consistent, loving, and tailored to your pet's needs. I follow each pet’s routine as closely as possible to keep them comfortable and stress-free. That includes feeding, walks or playtime, litter or potty breaks, and giving them plenty of attention (or space, if they prefer!). I always make sure their environment is safe, clean, and calm. In a client’s home, I respect their space and follow all instructions carefully to ensure their pet feels secure and well cared for.

About: I been a dog for 20+ years. I love letting dogs run, play and get exercise! I always make sure your dog is fed with fresh food & water everyday. I treat all animals like they are my own! I LOVE sending pet owners pictures of their pets while away! I am available most weekends and weekdays! Don’t ever hesitate to text me asking for updates! When I take your dog for a walk I make sure they go potty and get plenty of love! Over night stays are wonderful too! I have big comfy dog beds for your dog to stay on! I also provide lots of toys to play with as well. I live in a large 4 bedroom 2 bathroom home in Jenks, OK. I have access to several dog parks, TONS of walking paths and a great doggy exercise area! I look forward to taking care of your sweet babies while you’re away! I currently work full time remote. I am able to take breaks to tend to all animals during the day and in the evenings. I can be super flexible. I have a fenced in yard and a super sweet golden doodle to keep your dog company! Our neighborhood is perfect for long walks and I love giving treats!

“I highly recommend Amy as a dogsitter. She provides exceptional care for my dog, Biscuit, ensuring he is happy and well-cared for. Amy's dedication and attention to detail make her an excellent choice for anyone seeking a trustworthy and caring dogsitter.”


About: Caring for my own pets until their very last day taught me the importance of love, patience, and attentiveness. Now, for the first time in my life, I find myself without a pet, but I’ve started filling that hole by offering pet sitting as I heal. With years of hands-on experience, I’m skilled in administering medication, handling special diets, and providing gentle, compassionate care for pets with unique needs. Whether it’s daily walks, playtime, or simply being there for your pet, I offer dedicated care with a deep understanding of what it means to love and lose a furry family member. Working remotely allows me to be home and attentive throughout the day, making pet care a seamless part of my daily routine. I’m active, and my older kids (12 and 17) share my love for animals, so your pet will have plenty of company and playtime. I currently pet sit for multiple friends, so I’m experienced in managing different schedules and needs. I’m open to overnight stays or having your pet stay with us, and if your furry friend enjoys car rides, they’re welcome to join us on errands or school drop-offs. I’m flexible and committed to ensuring your pet’s comfort, whether they prefer staying home, riding along, or need to be crated. In my home, I create a warm and welcoming environment where pets can feel safe and loved. I ensure they have a comfortable space to relax, with plenty of toys, cozy spots for naps, and regular access to the outdoors if needed. I maintain their routine as closely as possible, from feeding schedules to playtime, and I’m attentive to any special needs, such as administering medication or adhering to dietary restrictions. My older kids also love interacting with pets, so there’s no shortage of attention and affection. When caring for pets in a client’s home, I make sure to respect and follow the established routines and guidelines. I provide updates, whether through photos or messages, to keep you informed and at ease while you’re away. I’m diligent about maintaining the cleanliness and order of your home, making sure your pet is well-cared for in their familiar surroundings. Whether it’s in my home or yours, I’m committed to providing the best care possible, tailored to the specific needs of your pet.

“She took care of Moose for the day as it was last minute and super early! She kept me updated throughout day! My pup had fun and is worn out. He had a blast! Highly recommend!”


“I really appreciate the care and attention Miya got while in his care. She was treated like a member of the family and that is important to me. I received pictures and videos and this helped me feel comfortable with Miya being under the weather. I would recommend and send Miya back again and again.”


About: I have had pets my whole life and love meeting new animals. I have a friendly, snuggly, 3 year old Cavapoo who does well with other dogs or cats. I have a flexible schedule. I am available a lot during the day and evenings to care for pets in your home or mine. I also have three kids who love animals plus an extroverted dog who loves company! I will respect the owners wishes regarding their pets care. Thank you for trusting me with your beloved pet! In my home you will find my dog snuggled up next to someone on the couch. I just want the animals to feel happy and loved!

About: I have had my own dogs ranging from 10 lbs to 70 lbs for the last 15 years. I love fur babies of all ages. I am a teacher, so my summer hours are very flexible for vacationers! During the school year my evenings and weekend hours are pretty flexible. I have a very larger fenced yard. I have 3 friendly dogs and a large crate. My babies are okay with being outside if your baby likes to be alone without other dogs. I’m very respectful of the homes of other people and am aware that the dog may be very protective of their home and may need some time and patience to warm up to me.

About: I have had dogs as pets as far back as I can remember. I truly feel a family isn’t complete without one of their own. I’ll care for yours like they’re my own. I work part time and will only be taking clients when I’m able to be at home (with the exception of an errand every once in a while). We live on a 17 acre farm and have two different sections fenced off for our dogs (approximately 1 total acre) to romp and play. My two are very playful and love company.
Loving doggy day care in your neighborhood
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Aleacia C.Star Sitter

“Aleacia is very quick at replying to texts and is very good about keeping me posted on how my dog is doing! She also sends nice pictures of my dog!”


Judy B.

“Judy was great! She was able to watch my dog all day last minute and sent me updates throughout the day!”


Stasia H.
Star Sitter

“Stasia loves pets almost as much as people. She is very mindful and caring when it comes to the health and well-being of pets. She takes the time to mix high quality vitamins and nutrients in their food. She active in engaging with play, exercise, and grooming. I wholeheartedly trust my dog in her care.”


Crystal & Lyle D.Star Sitter

“What an amazing app with opportunities to find animal lovers like Crystal who was quick to respond, sent us updates and flexible with our schedule. We drove over 8 hours out of town for a wedding, and not wanting to leave our dog in an AirBnB for the entire hectic day, leaving him with Crystal was the best decision! We could tell by photos he was well loved and enjoyed so much his time with them!! Thank you app creators and everyone willing to of care for pets when needed!!”


Erin P.Star Sitter

“Erin took very good care of Archie! She is very responsive, kind, and friendly!”


Evette A.Star Sitter

“My dog has such a great time every time Evette has him over for doggy daycare! She always takes such good care of my baby!”


Marta Ines D.
“Marta was so kind and sweet to my dog, my dog looked so happy to play and have loads of cuddles. Communication was very efficient and I had updates every day. I do definitely recommend her. Would love to use her services again.”


Toni W.Star Sitter
“Toni is great with my fur babies, treats them as her own. Very kind and caring. I would recommend her highly to take care of anyones fur babies.”


Tyler C.
About: I’ve been caring for pets since I was 10 years old, starting with family cats and dogs, and quickly becoming the go-to sitter for friends and neighbors. My wife and I began offering pet walking and sitting services in our local community when we were 16, and she’s now a certified pet groomer — I’ve assisted her with bathing, brushing, and keeping pets calm during grooming sessions. Over the years, I’ve cared for animals of all temperaments, from shy rescues to high-energy puppies and confident cats. I treat every pet as if they were my own, giving them patience, attention, and lots of love while making sure their daily routines are followed exactly. My schedule is completely open, which means I can give your pets as much time and attention as they need. Whether it’s early mornings, late nights, weekends, or last-minute requests, I’m available and ready to help. Your pet’s care will always be my top priority. I live in a small, quiet apartment with two sweet resident cats (no yard). My home is tidy and cat-safe—screens secured and doors monitored—with plenty of enrichment and calm spaces. I scoop litter twice daily, refresh water often, and follow exact feeding/medication instructions. For dogs, I provide care in your home or on walks only. I use gentle, patient handling and share frequent photo updates so you always know your pet is safe.


Desiree Jewel J.
Star Sitter

About: Hi! My passion has always been to work with animals. I started Pet sitting for my neighbor at 16. I was a Veterinary Assistant at 18. I was accepted into TCC's Vet Tech program but was encouraged to focus on my baby. I have always wanted to own my own Pet- Sitting business and now at 25 years old with 9 years of experience in pet-sitting, plus having many fur babies of my own throughout the years, I want to pursue my dream! I can't wait to meet you and your furry family! I am free and at home most of the time. The only times I am not available are 10 am to noon every Monday, Tuesday, Friday, and Saturday. I also go to church every Sunday from 10 am to noon. Other than those times, I am free to pet sit, dog walk, and board at any time. I have two senior medium-sized dogs (a boy and a girl) and one small female cat. All animals are fixed, and up to date on shots. The cat is not declawed. I give my female dog an insulin shot twice a day. I am capable of administering medication. Animals are allowed on the furniture. I also have a Five year old little boy which limits me to only boarding in my home. I can take care of animals in their homes as long as I am not required to spend the night in the home, I will visit as often as needed.


Logan W.

“We really appreciated Logan's professionalism and flexibility and he was very good with our dogs. My parents dog is a particularly nervous type and Logan seemed to know just how to make her comfortable. Dogs came home worn out after playing most of the day. Logan also was very flexible and accommodating with scheduling which we really appreciated. Overall, great experience.”


Sarrah M.
“Sarrah is very smart and always dependable. She was raised with cats and dogs and even hamsters. Always compassionate and loving with all animals she is in contact with. Sarrah is one of the most honest people I know, even if she is my daughter. You couldn't find anyone better to care for your fur babies than Sarrah!”


Natalie O.
About: I been a dog for 20+ years. I love letting dogs run, play and get exercise! I always make sure your dog is fed with fresh food & water everyday. I treat all animals like they are my own! I LOVE sending pet owners pictures of their pets while away! I am available most weekends and weekdays! Don’t ever hesitate to text me asking for updates! When I take your dog for a walk I make sure they go potty and get plenty of love! Over night stays are wonderful too! I have big comfy dog beds for your dog to stay on! I also provide lots of toys to play with as well. I live in a large 4 bedroom 2 bathroom home in Jenks, OK. I have access to several dog parks, TONS of walking paths and a great doggy exercise area! I look forward to taking care of your sweet babies while you’re away! I currently work full time remote. I am able to take breaks to tend to all animals during the day and in the evenings. I can be super flexible. I have a fenced in yard and a super sweet golden doodle to keep your dog company! Our neighborhood is perfect for long walks and I love giving treats!


Amy M.

“I highly recommend Amy as a dogsitter. She provides exceptional care for my dog, Biscuit, ensuring he is happy and well-cared for. Amy's dedication and attention to detail make her an excellent choice for anyone seeking a trustworthy and caring dogsitter.”


Lindsey R.
About: Caring for my own pets until their very last day taught me the importance of love, patience, and attentiveness. Now, for the first time in my life, I find myself without a pet, but I’ve started filling that hole by offering pet sitting as I heal. With years of hands-on experience, I’m skilled in administering medication, handling special diets, and providing gentle, compassionate care for pets with unique needs. Whether it’s daily walks, playtime, or simply being there for your pet, I offer dedicated care with a deep understanding of what it means to love and lose a furry family member. Working remotely allows me to be home and attentive throughout the day, making pet care a seamless part of my daily routine. I’m active, and my older kids (12 and 17) share my love for animals, so your pet will have plenty of company and playtime. I currently pet sit for multiple friends, so I’m experienced in managing different schedules and needs. I’m open to overnight stays or having your pet stay with us, and if your furry friend enjoys car rides, they’re welcome to join us on errands or school drop-offs. I’m flexible and committed to ensuring your pet’s comfort, whether they prefer staying home, riding along, or need to be crated. In my home, I create a warm and welcoming environment where pets can feel safe and loved. I ensure they have a comfortable space to relax, with plenty of toys, cozy spots for naps, and regular access to the outdoors if needed. I maintain their routine as closely as possible, from feeding schedules to playtime, and I’m attentive to any special needs, such as administering medication or adhering to dietary restrictions. My older kids also love interacting with pets, so there’s no shortage of attention and affection. When caring for pets in a client’s home, I make sure to respect and follow the established routines and guidelines. I provide updates, whether through photos or messages, to keep you informed and at ease while you’re away. I’m diligent about maintaining the cleanliness and order of your home, making sure your pet is well-cared for in their familiar surroundings. Whether it’s in my home or yours, I’m committed to providing the best care possible, tailored to the specific needs of your pet.


Omni B.Star Sitter

“She took care of Moose for the day as it was last minute and super early! She kept me updated throughout day! My pup had fun and is worn out. He had a blast! Highly recommend!”


Angel Daniel L.

“I really appreciate the care and attention Miya got while in his care. She was treated like a member of the family and that is important to me. I received pictures and videos and this helped me feel comfortable with Miya being under the weather. I would recommend and send Miya back again and again.”


JILL S.
“Jill will take great care of your family pets. She is dependable and trustworthy & very loving with all of our pets! I would highly recommend her!”


Kasey K.
“If you’re looking for someone to love your pets like they’re royalty (or, honestly, better than most people love their actual children), Kasey is your girl. She has a full on zoo/farm situation going on at home. She has dogs, cats, birds, chickens, fish, lizards and maybe a few squirrels she’s secretly rehabilitating, and every single one of them is her baby. I’m pretty sure her first emergency contact is her vet. Kasey will literally try to rescue every animal she sees. Injured pigeon on the sidewalk? She’s on it. Random stray that clearly belongs to someone else? She’s already got a leash. Even if the animal bites her and she’s bleeding out, she’s still like, “It’s not his fault, he’s just scared!” Watching a movie with her is an emotional rollercoaster, not because of the plot, but because she’s devastated if any animal gets hurt. But seriously, she’s the most responsible and loving pet mom you could ask for. She keeps up with medications, vet visits, and about 400 different feeding schedules. Your pets are in the absolute best hands with Kasey, and she’ll probably love them more than you do. (Just kidding… kind of.)”


Janelle C.
“I had an incredible experience with Janelle, and I highly recommend her services! She was attentive, caring, and showed genuine love for my pup. From the moment I met her, I could tell she was passionate about animals and dedicated to providing the best care possible. She followed all instructions diligently, ensuring my pet's feeding, exercise, and medication needs were met.. She also sent me regular updates and photos, which reassured me that my pet was in good hands. I couldn't have asked for a better pet sitter, and I wholeheartedly endorse her services to anyone in need of reliable and compassionate pet care.”
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1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
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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 Aug 2025 was about $30 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, 172 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, 93% of Winchester sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winchester have an average of 18 years of experience. Sitters offering doggy day care with repeat customers have an average of 2 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 172 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 100% of sitters offer daily exercise, 100% offer medication administration, and 85% 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.
