Doggy Day Care in Winston Terrace
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 Winston Terrace 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.


“Esteisy took wonderful care of our senior dog, Charlie. Her communication and responsiveness were exemplary. She sent many photos and updates, which we greatly appreciated.”


“We couldn’t be happier with the care Lyra and Scott provided for our dog, Olive. Every year, our family—about 30 of us—goes on a vacation together, and this year we weren’t sure we’d be able to go because we didn’t have a sitter for Olive. Fortunately, we found Lyra and Scott on Rover, and everything worked out perfectly. They live nearby and were incredibly flexible with our changing day-to-day schedule, which was essential since we were coordinating everything from our vacation. Olive isn’t comfortable being alone, and we were a bit unsure how she’d do around children. Lyra and Scott reassured us—and they were absolutely right. Olive did great, and they even sent us regular updates and photos of her spending time with their kids, which gave us so much peace of mind. Thanks to Lyra and Scott, we were able to fully enjoy our trip knowing Olive was in such great hands. We will definitely use them again In The future”



“Stephanie and Max take great care of our dog when we’re visiting Williamsburg enjoying the activities. It’s great to have a place we know our dog is well cared for and having a blast.”


“Christene's daycare was just what we needed. We had a fantastic meet and greet where our dogs got along great. After daycare, Willow seemed happy and excited. Best part, Willow smelled great at pickup (I can't say the same when she gets home from company daycares).”


“We had a wonderful experience with Jarin dog-sitting our dog, Lea, while we toured Williamsburg while on vacation. Jarin was communicative and positive. When we experienced car trouble on our road trip, she remained available and accommodating, which was a huge relief. Not only that but she fed Lea dinner and took her on multiple walks. We loved receiving all the photos and videos. Highly recommend Jarin for dog-sitting!”


About: I have grown up with animals. Dogs and cats are at the top of the list. I've been around domesticated animals all of my life. My first kittens at my young age was two siames kittens Who had 2 litters of kittens as well as having to toy poodle dogs, that had two litters of puppies twice. I must have been about 10 so it was from then that I have been loving & caring for fur babies.. Though I do not Own a dog or a cat right now, but look forward to owning some in my future.. I currently own a guinea pig. I just recently experienced the end of a pug/fur baby end of life. I took care of the pug for his last six months of life. Soon after that I boarded a beautiful pitbull for the weekend of mother's day. So to book with me, i'm sure I will have you covered.. Because I am home during the day I am a great fit for you fur baby. I love on your Fur baby while you are on occasion or just I'll have an a fun day. Because I am located across from freedom park in James City County, Williamsburg. I feel i'm in a great place to be able to get them out to go for walks and just run and play.

About: My family and friends call me the dog whisperer because I instantly form a special bond with every pup that I meet and care for! My current work schedule allows me the flexibility to be available for walks and potty breaks Monday through Friday 10AM- 2PM. The weekends are based on need. For care in my home I have a 10 year old mixed breed peek-a-poo. He gets along very well with other non aggressive male and female dogs. He is can be shy around other dogs but not aggressive. He loves children. I have 2 children ages 9 & 6. Our yard is not fenced in so we take our dog out for walks for his potty breaks

“Mary Beth was amazing! She treated our pup like her own furry child. She updated us with pictures and took our pup on multiple walks. I highly recommend her and will use her again on our next trip.”



About: "Whoever said diamonds are a girl's best friend...never owned a dog" I live in a townhouse in Williamsburg with husband, our 1 year old daughter and our puppy, Korben. Dog sitting is a full family experience in our home, both our daughter and puppy love it when we have house guests. In fact our daughter’s first word was “doggie”, so it’s very important that dogs that come into our home do well with children as much as they do well with other dogs. While we don’t have a fenced in yard we make up for it with a walking path in the neighborhood and many other walking trails close by, we generally go on two walks a day, weather permitting. I've been sitting for my friends and family for as long as I can remember. So if your looking for a place where your dog will be well cared for and have a lot of fun in the process, look no further. Please don't hesitate to e-mail me with further questions, I want you to feel comfortable when you leave your dog with me while you are out of town. I work mostly from home so your pup will have the hands on attention they deserve! We offer ample love and attention through walks and belly rubs. There are occasions I will need to leave the house for work, but I’m usually not gone more than an hour or so. In those instances we’ll recreate what you do with your pup when leave your home. I really try to mimic your routine at home as best as possible. I know that coming to a new home can be stressful for the pup so I try to ease that transition by sticking to your routine as best I can.

About: Welcome to our pack! We’re a retired military family of six—four humans, two pups, and a whole lot of dog-loving energy. Our crew includes our spunky Chihuahua, Jake, who runs the show, and our goofy Lab, Huck, who’s all about fetch and belly rubs. With two young animal whisperers (ages 5 and 12) leading the charge, we’ve been surrounded by wagging tails our whole lives—pets are family to us! Now, we’re opening our home (and hearts) to your furry friends. Whether it’s boarding in our cozy Williamsburg chalet, popping by for drop-ins at your place, or taking your pup on a walk to sniff out the neighborhood, we’ve got you covered. Our girls are thrilled to shower the dogs with love (and maybe a few extra treats). From our military days, we bring reliability and care to every tail-wagging task. Your pup will get the VIP treatment—playtime, cuddles, and a home-away-from-home vibe. Let’s make some new furry memories together!” Our family primarily works from home. Jeff has to travel from time to time, but Megan is always home to care for all your dogs needs when he is gone. I have a fenced yard and two playful loving pups to ensure they have constant companionship. Very safe and quiet environment with close walking access to Capital trail and low traffic neighborhood walks.


“Rocky and Willow stayed so we could go to Busch Gardens. Mary and Glen sent us photos and updates through the day. Thank goodness for them and for Rover so we could enjoy vacation and our pets had a safe place to play! We would def bring our fur babies here again!”


About: I’ve always been an animal lover, and caring for pets has been a part of my life for years. From playful puppies to senior dogs who need extra patience, I know how to adjust my care to fit each pet’s personality and needs. I have hands-on experience with feeding, walking, administering medications, crate training, and keeping pets comfortable while their owners are away. Friends and family often rely on me to watch their dogs and cats, and I treat every animal like they’re my own—plenty of cuddles, playtime, and attention included! Whether your pet is full of energy or just enjoys lounging around, I’ll make sure they feel safe, loved, and cared for at all times. Pet care is just a natural part of my day. I’m used to building my routine around feeding, walks, playtime, and lots of love. I make sure pets get their exercise, attention, and cuddles every single day, because I know how much those little things matter. Each week, I also set time aside for things like brushing, extra play, or whatever makes them happiest. Taking care of animals doesn’t feel like a chore to me — it’s something I truly enjoy and look forward to. I care for pets like they’re part of the family! In my home, they’ll have a safe, cozy space with plenty of love, playtime, and snuggles. In your home, I follow their normal routine so they feel comfortable and cared for—whether that’s walks, meals, meds, or cuddle time. Every pet is unique, and I make sure they get the attention and affection they deserve. 💕🐾

About: I have had animals since I was very young, including dogs, cats, and rodents! My first job was at the Humane Society of Southern Arizona, and I have worked in shelters and grooming salons since! I love all animals and have been professionally trained to take care of them and provide them with all the love and attention they need! I have a pretty open schedule as of now! I am a full time online student. I can work with you and am very flexible. It really depends on the owners request. I am wlling and happy to work with the owner to provide the specific care their pet needs.

About: I’ve taken care of dogs since I was a kid (my own, neighbors, friends, etc)! Growing up we always had multiple pups (large and small). I also have 5+ years of animal shelter volunteer experience. Volunteer experience includes maintaining animal hygiene and cleanliness of facilities, walking, grooming, training, and more. I work from home full time and have a flexible daily schedule so your fury friend will receive all the care and attention he/she needs! I recently moved to Williamsburg to a townhouse with a fenced in backyard. I am extremely flexible and am certain I can meet any needs your pup may have for all services offered!


“Grace R. - what a delightful person and wonderful experience! We were visiting the Williamsburg area with our tempermental terrier, Max on what has to have been the hotest days to date this early summer. We are so very grateful that Grace was able to take Max every day, keep him cool, hydrated and safe while we visited the many wonderful places to see in that area. Truly a life saver to have such confidence in the care our Max received. Thank you so very much, Grace!”


“Meaghan was very friendly and caring towards Mason. She accommodated us with our changing timeline and made it possible to visit Busch Gardens on our way through Williamsburg. If we’re ever back in the area and need a sitter we would definitely book with her again!”


About: Hi! I’ve taken care of all types of animals since I was 11. Neighbors, friends and family! I play, walk and feed their pets! I also take them on rides in the car to take them on walks at different places I’m a college student Tuesday’s and Thursday! Home the rest of the time, work in the er some days! Just want to care for animals and have a bond! I have two friendly older dogs! I walk them everyday feed them and play! Love on them and just make sure they are comfortable! Dogs are my everything I just want them to be comfortable and loved m
Loving doggy day care in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.




Esteisy M.Star Sitter

“Esteisy took wonderful care of our senior dog, Charlie. Her communication and responsiveness were exemplary. She sent many photos and updates, which we greatly appreciated.”


Maggie W.Star Sitter

“My pup nearly broke away from me when he saw Maggie and her family! He loves being there, and I love the sense of peace I have knowing he is such good hands!”


Lyra & Scott H.
Star Sitter


“We couldn’t be happier with the care Lyra and Scott provided for our dog, Olive. Every year, our family—about 30 of us—goes on a vacation together, and this year we weren’t sure we’d be able to go because we didn’t have a sitter for Olive. Fortunately, we found Lyra and Scott on Rover, and everything worked out perfectly. They live nearby and were incredibly flexible with our changing day-to-day schedule, which was essential since we were coordinating everything from our vacation. Olive isn’t comfortable being alone, and we were a bit unsure how she’d do around children. Lyra and Scott reassured us—and they were absolutely right. Olive did great, and they even sent us regular updates and photos of her spending time with their kids, which gave us so much peace of mind. Thanks to Lyra and Scott, we were able to fully enjoy our trip knowing Olive was in such great hands. We will definitely use them again In The future”




Stephanie M.
Star Sitter


“Stephanie and Max take great care of our dog when we’re visiting Williamsburg enjoying the activities. It’s great to have a place we know our dog is well cared for and having a blast.”


Christene H.Star Sitter

“Christene's daycare was just what we needed. We had a fantastic meet and greet where our dogs got along great. After daycare, Willow seemed happy and excited. Best part, Willow smelled great at pickup (I can't say the same when she gets home from company daycares).”


Jarin E.Star Sitter

“We had a wonderful experience with Jarin dog-sitting our dog, Lea, while we toured Williamsburg while on vacation. Jarin was communicative and positive. When we experienced car trouble on our road trip, she remained available and accommodating, which was a huge relief. Not only that but she fed Lea dinner and took her on multiple walks. We loved receiving all the photos and videos. Highly recommend Jarin for dog-sitting!”


Ethel S.
“Ethel is our neighbor, a quiet and responsible woman with sound advice and a huge heart. She watched over our senior dog, Tiberius, most days while we were at work, and overnight occasionally. She tended carefully to his needs, as he was paralyzed in his later years, and mostly blind. She studied his condition and always asked questions when she was unsure of what we would prefer, sending us updates every few hours when we were out of town on vacation. She ensured he always felt safe, comfortable and content. Ethel was right there with us the night Tiberius passed away; I thank God for the comfort she's given us all. Ethel is a perfect sitter, and a member of our family.”


Melissa R.

“Frankie had a great time with Melissa. We'll definitely use her services again.”


Kristen L.
About: My family and friends call me the dog whisperer because I instantly form a special bond with every pup that I meet and care for! My current work schedule allows me the flexibility to be available for walks and potty breaks Monday through Friday 10AM- 2PM. The weekends are based on need. For care in my home I have a 10 year old mixed breed peek-a-poo. He gets along very well with other non aggressive male and female dogs. He is can be shy around other dogs but not aggressive. He loves children. I have 2 children ages 9 & 6. Our yard is not fenced in so we take our dog out for walks for his potty breaks


ming d.

“Ming did an excellent job in working with us and acclimating Josie to her new environment. She was always excited to see him. We would definitely book with Ming again.”


Mary Beth W.

“Mary Beth was amazing! She treated our pup like her own furry child. She updated us with pictures and took our pup on multiple walks. I highly recommend her and will use her again on our next trip.”




Shalynn P.

“Shalynn has always been willing to help out with Wysper on a moments notice. Our dog loves to rough house with her dog Chloe. Shalynn is very attentive and makes sure the pups get plenty of exercise while they are in her care. -- Shalynn "Travel is as much a passion as ambition or love." ~L.E. Landon”


Jeffrey & Megan J.
“I can't recommend Jeff and his family enough! From the moment I met them, I could tell they had a true passion for dogs. They went above and beyond to ensure my pup was comfortable, happy, and well-cared for during my time away. Their attention to detail was amazing — from sending regular updates and photos to taking the time to ensure my dog’s specific needs were met. I felt completely at ease knowing my fur baby was in such capable and loving hands. Whether it's for a quick walk or extended care, they are truly the best! I’ll definitely be calling them again for future pet care. Thank you for taking such wonderful care of my dog!”




Mary H.


“Rocky and Willow stayed so we could go to Busch Gardens. Mary and Glen sent us photos and updates through the day. Thank goodness for them and for Rover so we could enjoy vacation and our pets had a safe place to play! We would def bring our fur babies here again!”


Amy B.
About: I’ve always been an animal lover, and caring for pets has been a part of my life for years. From playful puppies to senior dogs who need extra patience, I know how to adjust my care to fit each pet’s personality and needs. I have hands-on experience with feeding, walking, administering medications, crate training, and keeping pets comfortable while their owners are away. Friends and family often rely on me to watch their dogs and cats, and I treat every animal like they’re my own—plenty of cuddles, playtime, and attention included! Whether your pet is full of energy or just enjoys lounging around, I’ll make sure they feel safe, loved, and cared for at all times. Pet care is just a natural part of my day. I’m used to building my routine around feeding, walks, playtime, and lots of love. I make sure pets get their exercise, attention, and cuddles every single day, because I know how much those little things matter. Each week, I also set time aside for things like brushing, extra play, or whatever makes them happiest. Taking care of animals doesn’t feel like a chore to me — it’s something I truly enjoy and look forward to. I care for pets like they’re part of the family! In my home, they’ll have a safe, cozy space with plenty of love, playtime, and snuggles. In your home, I follow their normal routine so they feel comfortable and cared for—whether that’s walks, meals, meds, or cuddle time. Every pet is unique, and I make sure they get the attention and affection they deserve. 💕🐾


Victoria L.
About: I have had animals since I was very young, including dogs, cats, and rodents! My first job was at the Humane Society of Southern Arizona, and I have worked in shelters and grooming salons since! I love all animals and have been professionally trained to take care of them and provide them with all the love and attention they need! I have a pretty open schedule as of now! I am a full time online student. I can work with you and am very flexible. It really depends on the owners request. I am wlling and happy to work with the owner to provide the specific care their pet needs.


Kerrie Y.
About: I’ve taken care of dogs since I was a kid (my own, neighbors, friends, etc)! Growing up we always had multiple pups (large and small). I also have 5+ years of animal shelter volunteer experience. Volunteer experience includes maintaining animal hygiene and cleanliness of facilities, walking, grooming, training, and more. I work from home full time and have a flexible daily schedule so your fury friend will receive all the care and attention he/she needs! I recently moved to Williamsburg to a townhouse with a fenced in backyard. I am extremely flexible and am certain I can meet any needs your pup may have for all services offered!




Grace R.

“Grace R. - what a delightful person and wonderful experience! We were visiting the Williamsburg area with our tempermental terrier, Max on what has to have been the hotest days to date this early summer. We are so very grateful that Grace was able to take Max every day, keep him cool, hydrated and safe while we visited the many wonderful places to see in that area. Truly a life saver to have such confidence in the care our Max received. Thank you so very much, Grace!”


Meaghan O.

“Meaghan was very friendly and caring towards Mason. She accommodated us with our changing timeline and made it possible to visit Busch Gardens on our way through Williamsburg. If we’re ever back in the area and need a sitter we would definitely book with her again!”


Jordan R.
“Jordan is a bright hard working young woman who goes to VCU and works p/t at the hospital. She has grown up with dogs of her own and they absolutely love her. I love my 2dogs very much and wouldn’t hesitate to have Jordan care for them if need be.”
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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 Winston Terrace 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, 209 sitters provided doggy day care in Winston Terrace. 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, 94% of Winston Terrace sitters offering doggy day care respond in under an hour.
Sitters who provide doggy day care in Winston Terrace have an average of 15 years of experience. 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 Winston Terrace.
Winston Terrace 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 Winston Terrace 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 209 sitters offering doggy day care in Winston Terrace on Rover, so you’re sure to find the perfect match for your dog! In Winston Terrace, 100% of sitters offer daily exercise, 96% offer medication administration, and 92% 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.
