Dog Walking Winchester Village
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

Winchester Village, 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 taken care of many different animals. Cats, dogs, lizards: you name it! I’m experienced with big dogs who have lots of personality, as well as cats who can be skiddish and shy. I also have a cat and dog of my own, and have experience with administering medication for all your pet’s needs! I’m available for you and your pet when you need me. My schedule is very flexible, and we can always talk about what times work best for you and your pet’s needs. I am well-versed in the animal language. Having many pets of my own and other experiences with animals, I can understand exactly what your pet needs. I am a fun loving person that has lots of love and comfort for your animal!
About: I have taken care of animals all my life in all stages of life. I very much enjoy playing and running around with dogs and cats Im a Stay at home mom and unemployed looking for work and a work out I love animals so I'm excited to start hanging out with all animals I have a well trained dog who is crate trained while I'm gone so ik how to use a crate properly. I love to play and cuddle with all animals can't wait to meet your fur baby
About: Hi, I’m Sophie! I attended a vocational trade school where I studied Animal Science for three years. I gained hands-on experience caring for a variety of small and large animals, while learning proper handling and restraints, health and behavior, as well as how to safely administer oral and injectable medications. Through my training, I became certified in animal first aid and CPR. I also have experience caring for puppies/kittens, senior animals and pets with special needs, so I’m comfortable following detailed care instructions and maintaining consistent routines. Animals have always been a huge part of my life. I’ve grown up with both dogs and cats, and also worked at a kennel in high school, so I have spent years caring for pets of all ages, sizes, and personalities. Because of that, I understand that every pet has unique needs, and I give the best care and attention that I possibly can. Whether your pet loves long walks, playing in the yard, relaxing on the couch, or simply sticking to their normal routine, we are committed to making them feel safe, comfortable, and loved while you’re away. We will provide regular updates and photos so you can have peace of mind knowing your pet is receiving attentive, reliable care. We understand how much trust it takes to leave your pet in the care of someone else, and our goal is to make that experience as stress-free as possible for both you and your furry family member! :) Hey! I’m Dylan and I’m a lifelong animal lover with a ton of experience caring for both dogs and cats. I grew up on a farm and have always had multiple pets at a time, so I learned responsibility and animal care at a young age. I currently have 3 dogs and 4 cats of my own, and I love spending time with them—whether it’s going on runs with my dogs or cuddling up with my cats. I’m calm, patient, and always make sure animals feel safe and cared for. I treat every animal like they’re my own, with love and respect. Whether your pet needs a fun walk, some playtime, or just someone to keep them company, I’m here to make sure they feel loved and cared for while you’re away! I’m currently working a full-time job Monday through Thursday, from 6am until anywhere between 3pm and 5pm, depending on the day. I have Saturdays and Sundays off, and occasionally Fridays. Sophie works 2pm to 10pm a few days a week, her schedule is different every week. Since our schedules are opposite and Sophie has a bit more free time, one of us is always available to spend a good amount of time with your pet. The first thing we do when taking care of our own pets, or others pets, is let them out to go to the bathroom. Next, we prioritize feeding and medicating (if necessary) and cleaning and refilling all water bowls. Once everything important is taken care of, we then spend quality time with them, whether it’s playing fetch, cuddling or going for a walk. Before we leave, we make sure we let them back outside for a good while to make sure they take care of all of their business.

About: I am a lifelong animal lover with over 15 years of dedicated pet care experience who shares an instant bond with almost every pet I meet. As a proud pet parent to a 6 year old Heeler who is my absolute best friend and a cat I rescued from my driveway at just 6 weeks old, I have hands-on, daily experience managing diverse temperaments, intense exercise needs, and strict routines. My background spans the entire lifecycle of pet care, from nurturing young animals to providing compassionate senior care. I am entirely comfortable with specialized care requirements, including administering oral or topical medications, managing strict measurements or raw diets, and providing a calm, low-stress environment for high-anxiety or nervous pets. Raising a high energy working dog and a rescue kitten gives me firsthand experience with the unique needs, quirks, and daily routines of both dogs and cats. Pet care is my top priority and full-time focus. I am currently launching independent entrepreneurial ventures from home, which gives me complete control over my daily calendar and ultimate flexibility. I am available almost any time of day or week to dedicate myself fully to your pet. Your animal bestie will be my main priority, receiving constant supervision, timely potty breaks, and companionship. My flexible routine lets me adapt to your pet's exact daily schedule, ensuring they feel safe, comfortable, and fully cared for while you are away. Safety, structure, and peace of mind are the foundations of how I care for animals, whether they are staying at my home or yours. In my own household, my dog safely enjoys our yard because he knows his boundaries and responds instantly to commands. My cat on the other hand, lives a secure indoor lifestyle, with the occasional supervised leash walk! :) When caring for your pets, I balance absolute safety with plenty of engagement. For dogs, I maintain a strict policy of keeping them securely on a leash at all times unless we are within a securely fenced area, eliminating any risk of a dog running loose. Rest assured, structured fun is still a massive part of our day; we will enjoy plenty of energetic games, walks, and playtime, all while ensuring your furry family member remains completely safe and protected!

About: I have taken care of dogs, my whole life whether they were my own or somebody else’s I absolutely love animals your animal will always be safe in my care and have the best time. I’m currently a stay at home mom so if I leave the house, I only leave to go to the grocery store or to grab the little one something to eat if they want it I have a huge backyard my house backs up against the woods. We are not close to the road at all. You’re dog would never be let outside alone my kids would run around in the backyard with them 💕
About: What sets me apart is the genuine bond I build with each animal. I don’t just “watch” pets—I spend quality time with them so they feel safe and loved. I’m comfortable with high-energy puppies who need structure and play, as well as older pets who need slower, attentive care. I follow routines exactly and make sure your pet feels at home, even when you’re not. i’m available whenever you need me! i’m a part time server at a restaurant, so we can come up with a schedule that works for us both! and of course your pet. i will follow all instructions left to me! i will put your pets needs first, and make sure they are happy and content at all times!
“Christine does a phenomenal job caring for our puppy while we are at work. She responds immediately, takes a bunch of pics for us, and always ensures he is comfortable before leaving. Christine always makes sure to meet our specific needs and is very attentive with Arlo. We are so thankful to have such a reliable and kind person to assist us when needed.”

About: I don't have any pets myself, but I have lots of experience with them! I used to have chickens for several years, and I've also worked with horses as well. I gained a lot of experience working in a dog kennel, and became very comfortable with all different breeds and temperaments of both dogs and cats. I also have occasionally house sat for friends and family over the years and have taken care of several senior dogs. I love caring for animals and making sure they get the love and attention they deserve, so I can't wait to take care of your pet! Please be advised if your pet cannot be alone for more than just a few hours, I still work a full time job, so some days I might be working an 8 hour shift. My schedule changes week to week, so some days I might be able to stay with your pet the entire day but that will depend on my work schedule. Currently I am not able to care for any pets in my own home, but I very flexible and can care for your animals however you wish in your home.
About: Hi! My name is Julia, and I have loved animals for as long as I can remember. I have owned both dogs and cats since I was a child, so caring for pets has always been a natural and important part of my life. I have several years of experience with dog sitting and house sitting, and I understand how important it is to know your pets and home are in caring, trustworthy hands. I love all pets and enjoy getting to know each animal’s unique personality, routine, and needs. Whether your pet loves long walks, playtime, cuddles, or just a calm companion nearby, I will make sure they feel safe, loved, and well cared for while you are away. I am dependable, attentive, and respectful of each family’s home and pet care preferences. I would be happy to care for your furry family member and give them the same love and attention I would give my own pets! Pet care fits naturally into my daily routine because caring for animals has always been a part of my life. I’m used to planning my day around feeding times, walks, playtime, litter box care, check-ins, and making sure pets feel comfortable and safe. I enjoy having pets as part of my routine, whether that means starting the day with a walk, stopping by for a midday visit, or spending quiet time with a cat who just wants company nearby. I’m dependable and flexible, and I understand that pets do best when their normal schedule is followed as closely as possible. I’m happy to adjust my routine to match each pet’s needs, whether they need extra attention, medication reminders, playtime, or just someone calm and caring to keep them company while their family is away. I care for pets with patience, respect, and attention to their normal routine. In a client’s home, I follow all instructions carefully, including feeding schedules, walks, litter box care, medications or special needs, favorite toys, and any house rules. I know pets feel safest when things stay familiar, so I do my best to keep their routine calm and consistent while their family is away. I also treat every home with care and respect. I make sure doors are locked, food and water are refreshed, litter boxes or pet areas are kept clean, and pets are safe before I leave. I pay close attention to each pet’s behavior, comfort level, and personality, whether they are playful, shy, energetic, independent, or need a little extra reassurance. My goal is for pets to feel safe, loved, and comfortable, and for owners to feel confident knowing their pets and home are in trustworthy hands.

About: A lot of my clients and friends call me the animal whisperer because I have yet to met an animal that doesn't like me. I have grown up with animals, specifically dogs, all my life. Growing up with animals has made me realize that your pet is very much a part of the family so I treat each and every pet as if it were my own - with love and care. Animals have shown me the meaning of unconditional love without judgment. I work from home so I’m pretty flexible and pretty much make myself available for your pet. I especially love having an excuse to get out of the house to take care of your adorable furry pet :) I’m pretty good at handling multiple pets at once and can hold my own. I’ve handled walking multiple pets on leashes at the same time. I’ve handled a house full of pets. I watch them and give them the love they need while I’m with them :) no animal or animal task is too difficult for me.
About: Growing up I was always involved with the care and grooming of my mother's AKC American Cocker spaniel kennel and quickly fell in love with dogs. I've helped deliver 3 liters of puppies ensuring every fine detail of the process was done properly. I've assisted and led many rescue missions for strays and wildlife. I currently care for three rescue rabbits Layla, Monty, Zuko and one beagle/JackRussell mix, Copper. I'm lucky to have all my pets in my life and they truly enrich our lives for the better. I currently accepted a new job opportunity therefore my schedule is a little odd right now but message me and we can work out the details there. on a leash/harness or lead line in the yard. I do walks and or hikes- weather permitted. Allow outside with supervised fenced in playtime with toys
About: Hi, I am Becky and I am a lifelong animal lover. I have always had pets in my home since birth. My husband shares my passion for animals and has served as a Vet Tech in the Army. As we have traveled the world, we have watched pets of all ages and sizes. My kids love having furry friends visit and enjoy joining me when walking the dog. So much so, my daughter's first word was "kitten." In our home, we have a beautiful black lab, tortie kitty, and a handful of geckos that live in our backyard. Now that my three children are in school, I would love to assist you with dog walking, cat and dog boarding, and daily check-ins for any of your furry family members.
About: Welcome and thank you for your consideration! I encourage any questions you may have about the type of care I provide or my experience. I strive to be a dependable, reliable, trustworthy, and knowledgable caretaker. I believe in providing the level of care, respect, and attention to detail that I would personally insist upon for my own pets. Why I may be a good fit for you: ✨ Previous experience working in a veterinary clinic, including administering oral, topical, and injected medications. ✨ Experienced with "difficult" cases such as fearful, nervous, or spicy personalities, senior /disabled pet care, or homes with multiple animal species. ✨ I take on limited numbers of clients at a time to ensure that I'm able to commit undivided attention instead of rushing to beat the clock. ✨ 100% supportive of indoor and outdoor cameras -- the more the merrier! I work my primary job from home so my schedule is able to adjust pretty well to accommodate all of my client's schedules and needs. I do not over book myself to avoid issues with emergencies, other visits running over time, etc. I do start a timer at the beginning of the visits, but I do not intently stare at it or scramble to leave as soon as the time is up. I have a questionnaire that I ask all current and future clients to fill out. It asks about feeding, schedule, behavior, quirks, exercise, hiding places, trash bins, etc. to ensure that I can be prepared to handle anything that comes up. For example, I follow your instructions to the T with regards to feeding, whether it's wet, dry, raw, mixed, home cooked, or something in between.
About: I've taken care of dogs of every kind since my high school days. I love caring for and building relationships with dogs because they are truly like your best friend when they get to know and love you. Currently I work from home and for the most part make my own schedule every day. I am looking to build loving relationships with every pet that I care for so every owner can confidently put their trust in me to bring their furry friends back to me anytime they need me to take care of them. Me and my husband love dogs! We have a doggy park inside of our residence as well as a lovely community of people who walk their dogs everyday I’m sure your pet will meet some friends as we go out for walks and play at the park. Please let me know if you have any special food or any other request that you need me to accommodate to ensure that your furry baby is okay so I can be prepared as much as I can to welcome them into our home. I make my own schedule every day so i am pretty much free Monday through Sunday each week. I will make sure I update the time slots that are booked as clients start scheduling their appointments. All small and medium-sized dogs will be more than welcomed to roam freely around my living room kitchen area and are allowed to sit and lay on the couches as well. The floors are hardwood so even if they have an accident of pooping or peeing on the floor it will be alot easier for me to clean up on the hard floors than the carpeted areas. They will be allowed to come into my bedroom or any other room as long as I am in the room supervising them. I will take them outside to potty every 2 hours timed from the time they arrive until their scheduled time of leaving. You can feel free to bring their favorite toys they love to play with but I will also be purchasing brand new toys that I'm sure your dogs/cats will love to play with.
About: I have been pet sitting for a while! Overnights, drop ins, you name it. I have experience with puppies and elderly dogs. I have cared for my own dogs for ever as well. I am working full time 8-4 but I am available on weekends and most holidays. As well as weeknights or first thing in the mornings . I have one year old pup at home with a large fenced in yard. I have a one year old pup at home. We have a fenced in yard and go one walks in the park every few days.
About: I’m new to the area and excited to be living on the East Coast! I’ve spent my entire life around animals, and about 10 years ago I ran a successful pet-sitting business on the West Coast. I’m excited to get back to doing something I genuinely love. Over the years, I’ve cared for a wide variety of animals—dogs, cats, hamsters, hedgehogs, lizards, snakes, horses, goats, sheep, chickens, ducks, and plenty of others. I’m comfortable with dogs of all breeds, sizes, and personalities, from Pit Bulls to Chihuahuas and everything in between. I’m also comfortable caring for senior pets, puppies, anxious pets, animals with special needs, and pets who need medications. The one exception? Spiders. (((shudder))) Never spiders. I know every animal has their own personality, routine, and needs, so I’m happy to follow your instructions and care for your pets the way you do. Whether your pet needs a brief visit or several hours of companionship, I’m happy to tailor each visit to their needs. Walks, meals, medication, playtime, or simply some company—I’m happy to give your pets the attention they deserve. At this time, I’m offering check-in visits only and am not able to provide overnight care. I have a special-needs rescue dog of my own who cannot be left alone overnight. However, I can make as many visits during the day as your pets need and can stay for as long as necessary during each visit. I have plenty of references from previous pet-sitting clients and am happy to provide them upon request. I understand that trusting someone with your pets - and your home - is a big deal, and I want you to feel comfortable knowing they’re in good hands while you’re away. My goal is to make sure your pets are safe, happy, comfortable, and cared for just as you would want. My #1 priority is to provide loving care when you’re not there. I’m available all day, seven days a week—including holidays. I’m happy to accommodate early mornings, late nights, and even last-minute requests. I can work with your schedule. When I’m in a client’s home, I make it a priority to follow the pet’s normal routine and schedule. This helps ease the anxiety of having someone new in their space while their parents are away. I also respect your privacy—I know how it feels to have someone go through your belongings, and I could never imagine violating that trust.
The median cost per walk for dog walking in Winchester Village is $20
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- 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.

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It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Winchester Village
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester Village average 4 repeat dog walking clients
FAQs for Dog Walking - Winchester Village
Frequently asked questions about Rover
As of August 2026, there are 1,961 sitters on Rover offering Dog Walking across Winchester Village. 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 your Winchester Village. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winchester Village.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Winchester Village. On Rover:
- 96% of walkers can help with special care needs
- 96% can help with giving oral medications or injections
- 96% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.






