Dog Sitting in Winston
Book a Winston dog sitter to watch your dog in your sitter’s home or yours.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winston dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“John has been seeing our puppies for a while now and he is so good with them! There is always a noticeable difference in our pups on days that he comes to see them, and when we got a second puppy he was so nice and quickly adjusted to our feeding and potty training routine. 10/10 would definitely recommend John to take care of your dogs!”


About: I've been caring for pets for over 10 years — dogs and cats belonging to friends and family who trust me completely, and that trust means everything to me. What makes my care different is that it's never one-size-fits-all. If your dog lives for walks, we walk. If they're all about the ball, we play. If they just want to curl up next to someone, I'm right there. Every pet gets care shaped around who they are, not a standard routine. My home is child-free and pet-free, so your baby isn't competing for attention — they are the focus of my entire day. And when you pick them up? They'll be freshly bathed, happy, and ready to go home. Baths are always on me. PLEASE NOTE: I can board up to 4 pets from the same family at one time, as the pets all know each other. I do not take multiple pets from different families to board at the same time. It's often stressful for the animals and I don't get to enjoy your pet if he is stressed out by strange animals. My home is child-free and animal-free, which means your pet gets a calm, quiet environment with zero stress from other animals and no chaotic energy. They are the sole focus of my day. For dogs: I follow your routine to the letter — feeding times, walk schedule, medications, treats, favorite spots. I ease new guests in gently because I know the first few hours matter most. If your dog loves walks, we walk. If they're a ball dog, we play. They get care shaped around who they are, not a generic routine. Every dog goes home with a complimentary bath so they're clean, happy, and ready to see you. For cats: I understand cats aren't small dogs — they need something completely different. I give them a safe, quiet space to settle in at their own pace, no forcing interaction. I read their cues — whether they want lap time, window watching, or just a calm human nearby. Litter box hygiene is spotless and non-negotiable. I'm very careful about doors, windows, and escape points so your indoor cat stays safely indoors. For all pets: I monitor eating and behavior closely and flag anything off straight away. You'll get regular photo and video updates — as many or as few as you'd like. I've been caring for pets for over 10 years for people who trust me like family, and I take that trust seriously. My goal is simple: your baby comes home calm, happy, and exactly themselves. I do have a fenced yard but do not allow dogs to go out alone unsupervised. I enjoy walking dogs and will keep the routine that you have with your dog. I only take cats and dogs at the same time from the same family. I will always confirm any animal is up to date with vaccines and flea treatments first.
About: I was raised around animals and have animal care experience as well as animal training experience and veterinary assistant experience. I have always loved animals and look forward to getting to watch your babies. They will be greatly cared for while in my care. I work 3 days a week and I have the rest of the week off. My available days are my off days to watch you precious fur babies. I have two dogs of my own. One neutered male and one spayed female. They both love having new play mates. I have a fenced area at my apartment that lets animals run and play with obstacle course as well, so they will get to run out their energy.
“Very nice. My pets all warmed up to Michele instantly. I love knowing we have someone in our area willing to be a caregiver for our pets when we’re stepping away. Gives me piece of mind. No doubt.”

“Shurran is the best dog helper I’ve worked with so far!!! She was prompt, anticipated things I should consider for a smooth experience and she loved on my baby Max with genuine care. I’ll definitely be using her again and referring her to others. Thank you Shurran!!”

About: I have years of experience caring for a wide variety of dog breeds, as well as cats. From high-energy playtime and daily walks to providing the gentle, attentive care that senior dogs need, I know how to keep pets safe, happy, and comfortable. Neighbors, friends, and family have always trusted me to feed, walk, and look after their furry family members. I maintain a flexible part-time routine, which gives me plenty of dedicated time to focus on your pets! I am fully available for weekend boarding, and on weekdays, I am ready to step in for walks, playtime, and companionship anytime after 2:00 PM. Because my schedule is highly predictable, you can count on consistent routines and timely updates for your furry family members. Keeping pets safe and comfortable matters most here. A spacious, completely enclosed yard offers plenty of room for supervised outdoor activity. The household runs quietly, adjusting smoothly to each pet’s habits. Crating happens when preferred by the pet or requested by you. Every detail, including feeding schedules, medications, and special directions, is followed exactly as given.
“Stephanie has been caring for our three dogs for some time, and she has consistently been wonderful with them. It’s clear that she genuinely loves animals. During our most recent trip, our camera caught a chicken escaping, and Stephanie went above and beyond by safely catching the chicken and bringing her back home. We are extremely grateful for her exceptional care and dedication.”

About: Hello! My name is Jackie. I have been surrounded by animals all my life. I am 25 years old. I got into more experience with handling animals around 15 years of age. I’ve fostered four litters of kittens while finding them new homes. I have experience with bottle feeding. I have looked after friends and family’s dogs as well. I’ve taken dogs for walks, bathed them and other necessary things they needed such as medications. I would like to provide you with the comfort of knowing that your pet is in good, loving care! Pet care fits well into my routine because I currently attend school only twice a week. This allows me to have a flexible schedule for walks, drop-in visits, and house sitting. I’m able to plan my days around the pets I’m caring for to make sure they receive consistent attention, exercise, and care throughout the day. Even on school days, I make sure to schedule visits and check-ins so pets stay on their normal routine. My goal is to keep pets comfortable by following their normal routine as closely as possible. I provide walks, playtime, feeding, and lots of attention while making sure they feel safe and relaxed in their own environment. I currently care for pets in the client’s home through drop-ins, walks, or house sitting and do not bring pets into my own home. I always send updates and photos so owners know their pets are doing well.
About: As a fellow pet owner, I enjoy reading and talking to my dog. It is my belief that he understand every would I am saying. He always let's me know he is listening when he raises his ears and turns his head toward me as I am speaking. We both love the outdoors and every chance we get, outside is where we are. Blue' loves to walk by the lake or sit by water. Water is very calming. Sometimes, while at the park, I will take a book to read, a blanket and we will sit by the water to relax. Blue also loves to look at the ducks in the pond. In taking care of other dogs, as a dog sitter, I plan to follow instructions from the owner(s). It is my value to treat another dog as if it where my own, with love and care. I have a huge back yard where the animals can get lots of exercise and outdoor time. In addition, I have a separate fenced in area for the dogs who may want to just go potty and chill while the others are running around the yard. Blue' and I look forward to meeting and sharing out space with other dogs. Our home is your pets home away from home!
“Taylor was timely, attentive and empathetic to the needs of our senior girl. She is knowledgeable able animal health and we were very comfortable that she could handle any issues that might have occurred. She is also a very pleasant person and we will certainly use her services again if needed.”

“Ashley was great, she went above and beyond to take care of our kitties and make sure they were happy and stress free. She sent pictures of each cat for every visit and each time the litter boxes were cleaned. She diligently cleaned our cats litter every day and disposed of it in the residential complex dumpster (close proximity), saving us from the chore of taking out the trash when we returned home. My cat, Knox who is quite shy warmed up to her quickly. She is very thoughtful and makes the effort to play and bond with your pet. I would recommend her pet services to any of my dear friends and family.”

“Charity is highly responsible. She ensured my cat was visited and fed every day within the timeline I preferred. It is a great relief to not have to worry about anything while away. She ensured my cat was well taken care of. Thank you Charity!”

“Kourtney- was amazing and did a great job with a last minute drop in.. She was a life saver to us! I would most definitely book again with her. Thank you, Toni and Blu”
About: I've had pets since I was young. Every pet I've had has lived a long and healthy life. I use to find wounded animals around the neighborhood and tend to them until they were healthy. I'd care for neighbors pets while they were gone all the time. As of now I am free anytime Friday to Sunday and overnights. Soon I will be full time at home and will be available everyday. I have a yard with no fence and a large basement for running around and a 12 week old puppy. Gets feed regularly. And walked at least 5 times a day.
About: I take my time to understand each dog’s wonderful personality, specific routine and needs. Making sure they feel safe, happy, and loved while you’re away. I am a serial entrepreneur so I create my own schedule. I love being able to spend quality time with my pets throughout the day. Often taking them to the park or just to get fresh air throughout the week. I have a dog crate and play area, toys and a large backyard with a tie out. I will follow whatever instructions you would like so that your pet is cared for properly.
About: I’ve taken care of dogs since I was 20 I've had my own pets and I have experience caring for dogs of all different sizes and breeds. Family members have put trust in me to take care of their pets. I’m a lover of all pets, young and old. We can do so many fun things I am sure I will pamper your pooch. I live in a house with a fenced yard and friendly neighbors! I live in a house with a fenced backyard. Many of my neighbors own dogs and you can see them walking their dogs in the neighborhood. My home is clean, fun and lovable.
Over 44 pet parents in Winston have booked dog sitting
Popular requests near you
Select a filter and find qualifying Winston 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!
The median cost per night for dog sitting in Winston is $20
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.
Sitters in Winston average 7 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Winston on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 5,100 dog sitters in Winston. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 86% of Winston dog sitters respond in under an hour.
Dog sitters in Winston have an average of 14 years of experience. Dog sitters with repeat customers have an average of 7 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winston.
Rover makes it easy to find Winston dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 5,100 dog sitters in Winston on Rover, so you’re sure to find the perfect match for your dog! In Winston, 97% of dog sitters offer daily exercise, 96% offer medication administration, and 94% 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 dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks 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 dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.



