Pet Sitting in Winston
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winston pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Tiffany was great, despite the 7 lbs of screaming tiny dog. That she was willing to try with Duke was awesome, and I appreciate it so much! Of course our old man, Pimp'ns, loved her, and he's the one that matters (old, can't hold his bladder all day any more). Thank you!!”

“Alicia has been our sitter for a few weeks now, coming to the house twice a week while I’m at school—and she’s done a wonderful job! She’s reliable, quick to respond, kind, and clearly loves what she does. I always come home to a happy, relaxed Lassie. Alicia goes above and beyond to make sure Lassie gets plenty of fetch time and potty breaks. I highly recommend her!!”

“When I was planning a trip out of town and my original sitter fell through, Heather was able to make availability short notice. She took excellent care of my kitty, giving me updates and pictures every day. She definitely went above and beyond and I felt so much better about being away knowing that she was taking care of my old man cat.”

About: I’ve had dogs since I was a kid. I’ve cared for friends and families dogs of all sizes and ages. I currently have a female American bully but in the past I’ve had English mastiffs, pit bulls, and a border collie. I enjoy high energy dogs that love to run and play as well as older dogs that just want to play around and be loved on. I’m currently on summer break. I am an athlete at Eastern Kentucky University and have required practices every day but I’m gone no longer than 3 hours per day. I currently live in an apartment with a dog park on site I also have one friendly and very active pup to keep yours company. I will always be outside with the pups they are never out there alone.
About: I've taken care of friends and families pets for the past 10 years, I've worked in pet retail for more then 9 years. My growth and passion for animals is every evolving I currently work a full time job, so I have 2 rotating days off a week plus off every night. Schedule and times can always be discussed. I have 8+ years of pet education along with nutrition and training, I have more then 40 hour of positive/ positive reinforcement training to help keep things under control.
“Elena is AMAZING!!! She is so sweet, kind, caring, patient and very accommodating. Our dog, Sydney is very shy and nervous around people, but she quickly warmed up to her. Elena took great care of Sydney. She gave detailed feedback, updates and pictures of Sydney during each visit. I will definitely rebook with Elena again. I highly recommend and trust her! Elena is the BEST!!!”

“As always, Cindy was excellent with Willow. It was storming so she sent a message and asked how Willow does with storms. It was so nice that she checked. But that’s how seriously she takes her appointments.”

About: I’ve been surrounded by animals my entire life—I’ve never known a home without a dog. Growing up, I had the opportunity to care for dogs of all sizes and temperaments, from energetic Jack Russell Terriers to loyal Labrador Retrievers and loving Pitbulls. I was always involved in their daily care, whether it was taking them on walks, feeding them, or making sure they stayed up to date with vet visits. My love for animals has only grown over the years. Two years ago, I adopted my dog, Russell, from a shelter, and he has been my loyal companion ever since. I also have two cats, Chief and Reid, who keep life interesting and have taught me even more about pet care. Caring for animals isn’t just something I do—it’s something I’m truly passionate about. I love making sure pets feel safe, happy, and well cared for, and I treat every animal as if they were my own. As a part-time Graduate Assistant, I have plenty of flexibility throughout the day to care for and play with your pups, especially on the weekends! As a dog owner myself, I know what it's like to worry about your pet while gone. I will ensure pets are fed, exercised, and groomed according to their needs. I provide loving companionship, and follow specific care instructions for each pet’s well being and comfort.
“Kailey has been absolutely wonderful with my dog, Sable. She’s dependable, punctual, and communicates clearly, which gives me real peace of mind while I’m at work. Sable took to her quickly, and it’s obvious Kailey genuinely cares about the dogs she works with. She’s flexible with my rotating schedule and always professional. I truly appreciate her reliability and would highly recommend her to anyone looking for a trustworthy and caring dog walker.”

About: I grew up in a house with dog lovers, so we had as many as 4 dogs at one point! We have had dogs from puppies to final days! I'm super comfortable with any breed! I'm currently a PA student, so my availability is pretty flexible. I'm usually always free on the weekends when most people need pet sitters for exciting weekend plans! I'm usually always free in the evenings during the week, as well. I can do whatever you need for your fur baby while away! I know how it is to be so nervous that your babies aren't taken care of while you have relatively no control since you aren't home! I will do whatever you need to ensure they are completely taken care of!
“I recently moved from NY to KY and was in need of someone to help care for my four dogs. I had spoken to many people and wasn’t comfortable with anyone as I had my prior dog walker in Ny for over 10 years. I found Tanika and she and I hit it off right away: she was super accommodating to my ever changing schedule. I was nervous to have my one rescue dog meet anyone because he could be unpredictable. Tanika came armed with treats and was relaxed and so easy going with all the dogs that he took to her first!!!! Tanika had been above and beyond amazing . She helps with my dogs that have medical issues and she is always there when and if I need her. She takes care of my dogs as if they were her own and I’ve never had to worry about them when I’m away. She is an absolute god send and I highly recommend her!”

About: With your pets permission, they will be loved on. Pets in my care will be treated like family. I have been around pets of all kinds my whole life and have pet sat for over 5 years! The only days of the week where I’m out for more than 3 hours is Tuesdays and Thursdays. I am at home otherwise, the more time I have with your pet, the better! I do have two cats, so they will likely be separated from your pets in a boarding situation, but I live next to a dog park so it is easily accessible for pups. I have many cat toys and treat varieties as well.
“Selah did a fantastic job. This was our first time using rover and she did not disappoint. She kept me well informed of messes, updates and earned our dogs trust. She even picked up our trash cans when the wind blew them over. Highly recommend using her to care for your fur baby.”

About: What sets me apart from other sitters is my patience, attention to detail, and genuine love for animals of all personalities. I have two labs and two cats of my own, including a rescue we welcomed into our home, so I understand how important trust, routine, and a calm environment are for pets. I successfully introduced all of our animals and helped them learn to coexist comfortably, which gave me valuable experience with animal behavior, slow introductions, and reading body language. I’m comfortable caring for both energetic and anxious pets, and I take pride in making animals feel safe, loved, and relaxed while their owners are away. I also genuinely enjoy the little things that make a difference — keeping spaces clean, deep-cleaning litter boxes, sticking to routines, and giving pets individualized attention based on their needs and personalities. 🐾 Pet care is already a huge part of my daily life, so caring for other animals fits naturally into my routine. Between my two labs and two cats, I’m used to managing feeding schedules, walks, playtime, cleaning, and making sure each pet gets individual attention and affection every day. I genuinely enjoy spending time with animals, so pet care never feels like a chore to me — it’s something that brings me peace and happiness. I’m someone who pays attention to the little details, whether that’s noticing changes in behavior, keeping litter boxes and living spaces clean, or helping pets feel comfortable and safe in their own environment. My schedule allows me to be dependable, communicative, and consistent with the care I provide, which I know is important when someone is trusting me with a beloved pet.
About: I have experience with puppy training basics, including house training reinforcement, crate training, leash manners, and maintaining consistent routines. I’m patient, calm, and positive, which helps young dogs learn while feeling safe and confident. For senior pets, I provide attentive, compassionate care, including administering medications, assisting with mobility, sticking to specialized diets, and monitoring for any changes in behavior or health. I understand that older pets need extra patience and gentle handling, and I make their comfort a top priority. Above all, I treat every pet as if they were my own—providing reliable, loving, and trustworthy care while keeping owners updated and worry-free. I am currently staying at home due to a lapse in full time work! Taking care of my pets is naturally in my daily routine as well as working on commission based art work. When it comes to taking care of pets in home, I am able to safely separate them from my other pets if need be. All of my pets are vaccinated! I do not have a fenced in yard, however I do have a gated porch! If your pups need walked they will be safely walked on a leash or they can be placed in my outside kennel if requested by you! :) pets are allowed on furniture!
About: We work from home full-time, which means your pup will get lots of supervision, attention, companionship, and cuddles throughout the day instead of being left alone for long periods. Dogs staying with us typically get up to two walks a day, usually 1–2.5 mile walks at nearby trails. If your pup enjoys walks and adventures, they’re welcome to join! We also make sure dogs have plenty of supervised playtime, enrichment, rest, and individualized attention depending on their personality and energy level. We genuinely love pets and try to make them feel like part of the family while they’re here. Whether your dog is playful, cuddly, shy, energetic, or prefers a calmer environment, we do our best to adapt to their needs and routine. We're also happy to provide regular updates, photos, and videos so you can feel comfortable while you’re away. We know how important it is to trust the person caring for your pet, and we aim to create a safe, loving environment where both you and your pup feel comfortable. I have a flexible schedule to give your pets the love and attention they deserve! I take my dog on walks twice a day for 1-2.5 miles in the park and typically spend the rest of the day at home, treating your babies like my own. I have a fenced yard and live walking distance from a park with wooded trails. I have a friendly pup in my home who loves having friends to play with. I will care for your pets like my own!
Winston pet parents share their Rover experiences
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It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
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Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Winston.
Rover makes it easy to find Winston pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.






