Dog Walking Winston
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Winston, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve been caring for pets for over 7 years, and it’s something I genuinely love. I have experience with dogs of all sizes from energetic puppies to senior dogs who need extra care and attention. I treat every pet like family and always make sure they feel safe, comfortable, and loved. Pet care is a regular and rewarding part of my weekly routine. I’m calm, dependable, and attentive to each pet’s needs making sure they get the right balance of exercise, playtime, and rest throughout the day. Pets stay in a clean, cozy, and pet-friendly space with plenty of room to relax or play, including a fully fenced yard where they can safely explore and enjoy the outdoors. There’s always someone home even if I need to step out briefly, my mom grandma or my boyfriend, who are both equally experienced and caring with pets, are always around to help. I usually introduce them during meet and greets so everyone feels comfortable and at ease
About: I have always looked after pets of friends and family. Thankful to have my lab best friend for the past 3 years, and want to share the love for other pet parents. I’m looking to support those needing one time support for emergencies or back up help when your regular sitter is unavailable. Message me for more information I am unable to offer services in my home but able to provide comfort to your pet in your home! I always aim for exercise, good meals, treats, and lots of love.
“Roland's first time with Scrappy. I certainly appreciated his input. Very knowledgeable and helpful. Would highly recommend Roland , for whatever your dog needs...Looking forward to have him walk Scrappy again.”
About: I have 20+ years of pet experience with dogs, cats, horses, goats, pigs, chickens, and more. I am available for dog boarding in my home for multiple dogs. I am comfortable giving medications. I can make multiple visits to your home while you are gone. Let me know what your needs are and we can find a suitable accommodation for your pet. They will be loved like our own. I am a stay at home mom who homeschools my children. Most of our days are wide open and I can easily accommodate taking care of other pets. I will look after your pets like I do my own. I will make sure they always have the proper food and water and are never left unattended. I can meet a variety of needs for many different pets.
About: Hi! I’m an experienced animal care professional with 15 years of experience as a zookeeper, and animals have always been a huge part of my life. Throughout my career, I’ve had the privilege of caring for and working with all kinds of species, giving me a deep understanding of animal behavior, individual needs, and the importance of patience, compassion, and trust. Whether your pet is playful and energetic, shy and nervous, senior, or simply loves some extra attention, I’m comfortable meeting them where they are and providing care tailored to their personality and routine. I know how important it is to feel confident that your pets are safe, happy, and well cared for while you’re away. I treat every animal in my care as an individual and take pride in providing dependable, attentive, and loving care. I’d love the opportunity to get to know your pets and give them the same care and attention I would want for my own! I work from home with a flexible part-time schedule, giving me plenty of time and availability to provide attentive care and drop-in visits for your pets. Since I have pets of my own, I primarily focus on drop-in visits. However, I’m always happy to discuss other options to find the best arrangement for you and your pets.
About: I've consistently had at least one cat and dog in my household at all times, if not two! I took Small Animal Care 1&2 in high-school. Durring summer breaks I went to horse camp where we learned how to safely handle, ride, and groom horses. I occasionally take care of my neighbors chickens when they go on vacation. I am currently working part-time and my schedule is made on a monthly basis. I'm available most weekends and weekdays after 1pm. Can do early mornings and late potty breaks. The house I live in has a large front yard and a larger backyard. It is unfenced but in a safe neighborhood that's perfect for walking
About: I'm an animal lover that grew up in the northern VA area. I've had pets since I was a child, large and small. I'm willing to care for furry, feathered or caged friends, as well as, farm animals. To me, no home seems complete without a loving pet around. I will treat your pet as if it were my own. I can provide morning visits, afternoon visits, evening visits, house sitting, walks, etc. I’m experienced with senior pets, chronic illnesses and injuries, as well as administering medication. I'm flexible and ready to provide you a wonderful service and loving care. I'm here to help keep your pet safe and happy when you’re away. My availability is open to care for your animals, we can discuss your needs and determine a preferred plan. I will come to you as needed. I can offer my services in the comfort of your own home throughout the day, caring for your pets and house sitting if needed. We can walk, play or just give some attention.
About: I was raised with dogs (shelties, primarily) and now have a hobby farm with goats, dogs (german shepherds, a lab and a sheltie), ducks and a cat. I'm reliable and friendly and happy to follow whatever instruction and routine you need. Your pets will be well cared for and you'll receive plenty of photo updates while you're gone! I have a very flexible schedule, so I am able to accommodate nearly any routine your pet is used to, including frequent walks and potty breaks. I will work with you to keep your pet's schedule as close to what they are used to as possible. If boarding in my home, we have a fenced yard, plenty of area to go on leashed walks, and they will get plenty of one on one attention and care. I'm happy to do transport or add in a bath during your pet's stay so your life can be as simple as possible while you're trying to get out the door for your trip. Pet care is my full time job and priority. I can adapt as needed to make sure your pet keeps the routine they are comfortable with, even when you aren’t home. I will ask questions and take notes on your pets’ routine and then do my best to ensure that those habits are in place with me.
About: Hi!! I am the owner of Pets and Pastures Pet Care, LLC. I’ve been pet sitting for over 10 years and have experience caring for a wide variety of animals including dogs, cats, turtles, and fish. Friends and neighbors have always trusted me to look after their pets while they're away, knowing they'll be in good hands. Currently, I live on a farm with two horses, three dogs, six cats, one pig, and chickens, so I’m very comfortable around animals of all kinds. I provide services in Castleton, Amissville, Rixeyville, Little Washington, Warrenton, and Culpeper. I am willing to travel to other towns. Your pet’s comfort and safety are my top priorities. I take the time to understand each animal’s unique needs and personality to ensure they feel safe, happy, and well-cared for in your absence. I offer flexible pet sitting services, including multiple daily drop-ins or dog walks. I’ll also provide daily photo updates so you can stay connected with your fur baby while you're away. I am negotiable with prices. Please feel free to reach out! I’d love to meet you and your fur babies!! I'm currently pet sitting full-time and working part time at RAWL, so I’m likely to be available when you need me. I occasionally manage multiple homes at once, so scheduling is usually not a problem. I carefully follow all instructions when caring for pets to ensure they are comfortable and happy while their owner is away. My goal is to give pet owners peace of mind so they can fully enjoy their vacation. I always make sure pets receive plenty of attention, are well cared for, fed on time, and given any necessary medications.
About: I believe you treat all animals like if they are your pet. I’m known to overly spoil my animals with love, funny voices, and care. I will keep you updated with pictures and videos and your pets are in exceptional care. I have an open schedule to cover their needs and care while I’m on duty and they become my family for the time they are with me. I’ve been taking care of cats and dogs for over 15 years typically small and medium sized dogs. I do have experience with some larger breeds on basic essential needs and care. I went through a battle of IVDD with my French Bulldog who passed which took a role on how I view the time with animals in general. I have an open schedule and extremely accommodating to your needs. I can work around the necessary schedule. I work this full time and if I don’t have any sitting I also run deliveries. I have a safe and trusted environment. I have one dog who gets along with other dogs but he is hyper and wants to play and nap consistently. I have a cat who does her own thing so my house is relaxed. No little kids and just me and my partner which she works from home so there’s always someone at home.
About: I have taken care of all kinds of dogs and cats from all walks of life and at all stages of life for the last twelve years! I am currently working part-time, so am flexible with scheduling for both weekdays and weekends during the day and evenings, as well! I am also available for overnight sitting. In my experience, each doggo and kitty has their own needs, which help them flourish best, so I abide by each fur baby’s routine and comfort level!
About: As an avid, pet lover I will take care of your pets, as if they were my own. I love cats and dogs and other small little creatures. Currently right now I have a pretty flexible schedule working from home so I have an ability to take care of your pets during the day. I will make sure your pets are safe in my care. When we go for walks I will always have them leashed and protect them from other animals.
About: Taken care of animals for over 10 years, held snakes, rode horses, pet tarantulas, I've been able to identify when dogs need to be left alone and when they were in danger or Ill could identify my dog had kidney stones, deeply care for animals and can walk, play, and be their best friend lol No job currently unemployed and I love animals so I'm chilling at the home right now for this year until I get married period and then I'll stay home even longer! I am able to really do anything you ask of me all I ask is that you let me care for your pets more than once! I will offer really lots of bonuses because I care
“Really liked meeting with Emily. She was super friendly and my dog hit it right off with her at the meet and greet. When she came to take care of my dog she was on time and left a great message with details about the walk. TOTALLY will be using her again and 100% recommend.”
The median cost per walk for dog walking in Winston is $20
Dog parents share their Rover experiences - Winston
Katie has been absolutely amazing with Cas, he’s a bit of a tough cookie requiring lots of patience due to him being older and partially deaf/blind. Me being chronically ill and working with long commutes, Katie has been a lifesaver and accommodated last minute requests! Highly recommend.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog walking
1. Search
Browse profiles of walkers near you who offer dog walking.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog walking - Winston
Select a filter and find qualifying sitters offering dog walking.Sitters in Winston average 3 repeat dog walking clients
FAQs for Dog Walking - Winston
Frequently asked questions about Rover
As of November 2026, there are 912 sitters on Rover offering Dog Walking across Winston. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in Winston. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Winston after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the walk begins.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.
Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.
Yes, you can find walkers who have experience with handling special pet needs in Winston. On Rover:
- 89% of walkers can help with special care needs
- 95% can help with giving oral medications or injections
- 98% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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