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

Over 6 pet parents in Winchester have booked dog walking
Winchester, Find top rated dog walking
Prices are estimates per walk for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“I have used Cyrissa over 15 times and she has done a fabulous with my Luna. She responds quickly to my requests and is very communicative She gets Luna out for a good walk every time she comes- they go about a mile which I truly appreciate. I’m not paying her to take her out to just let her lay on the grass for the majority of the time (I’ve had other people do that). I want Luna to get out and exercise and Cyrissa does just that. I 100% trust her in my home and with my dog. I’m lucky to have found her.”

About: "I bond with pets instantly, offering playful training for pups and gentle care the for seniors. My 20 years bring youthful energy and responsible attention." Pet care is a big part of my day. I schedule in walks, playtime, feeding, and grooming, making sure each pet gets the attention they need! Because I have dogs of y own and been a dog owner since I was about 10 years old! In my home and yours, I prioritize safety with secure spaces and constant supervision. Trust is built through consistent, loving care, creating a stress-free environment.
About: I have experience with all shapes, sizes and temperaments of animals. I currently own two large dogs. I have experience walking reactive dogs and fearful dogs. I have also cared for elderly pets and trained quite a few puppies! Knowing how particular I am with my own pets, I take your care instructions extremely seriously and will ensure you pet has nothing but the best while you are away. I work from home and am my own boss so my time is very flexible to give your pet all that they need! I can do check-ins or walks all times of the day. I am happy to follow your lead on whatever you like your dog to do every day! Backyard playing or walks around the neighborhood. Whatever your dog likes best, I can do!
About: I have experience working with puppies and many breeds. I will reinforce desirable behaviors through positive reinforcement. I have experience giving medication. I can take your pet to the vet for you. I have many years of experience working with animals at a veterinary hospital and animal shelter/rescue. I am available short or long term. I am available week days and weekends. Caring for pets is my vocation. I don’t have any schedule restrictions I have outdoor and indoor space according to your pet’s preferences. While outdoors, your pet will be supervised in an enclosed yard. I provide opportunity for water loving dogs to play in the pet pool. I provide “nose work” for those dogs that need mental activities.
About: What sets me apart is the trust I've built with my clients. Many are repeat clients who feel comfortable leaving their pets in my care, even for vacations lasting over a month long. I'm reliable, highly responsive, and believe communication is key. I'll keep you updated with photos and messages while following your pet's routine to help them feel safe, comfortable, and loved. From tiny cats to large dogs, I treat every animal as if they were my own and every home with the utmost respect, so you can enjoy your time away with complete peace of mind. I have a flexible schedule, which allows me to provide pets with plenty of attention, exercise, and companionship throughout the day rather than just quick check-ins. Whether it's walks, playtime, feeding, or simply keeping them company, I enjoy making sure each pet feels comfortable and cared for. As a pet owner myself, I understand the importance of consistency and sticking to your pet's normal routine. I always strive to make them feel safe, happy, and loved while you're away. I believe pets are happiest when they can stick to their normal routine. During overnight stays, I provide full care including feeding, fresh water, walks, potty breaks, playtime, cuddles, and any medications or special instructions if needed.
About: I offer personalized care with genuine love for pets, ensuring they feel at home and receive individual attention tailored to their needs. Since I don’t have any pets of my own, all my affection and focus will be dedicated to your furry friend, providing endless love, cuddles, and scratches to make them feel truly cherished. I have a flexible work schedule that allows me to care for your furry friend throughout the day. I make sure they’re fed, watered, and get plenty of outdoor time. I have a yard that gives pets more space to play, relax, and get their energy out, and I also love taking them on walks for extra exercise and stimulation. In both my home and your pet’s home, I prioritize safety, trust, and a nurturing environment. I ensure safety by securing all areas to prevent accidents and regularly checking for potential hazards. Trust is central to my care approach, so I maintain open communication with you, providing regular updates on your pet’s well-being. I create a comfortable and clean environment tailored to your pet’s needs, with consistent routines and plenty of affection to make them feel secure and loved.
About: Our dogs are our fur babies. Being a dog owner myself for 18years, I know how important it is to make sure they are in the care of someone you trust to give them the love and care they deserve. I hope I can be that for your pup. I have 18 years of pet care experience including training, giving medication, bathing, and ear cleaning. I have experience with many different breeds and dogs of all sizes, small, medium, and large. I am able to provide your dog with what they need physically as well. Whether that be a slow walk, a run, extra play time, or cuddles! I can’t wait to meet you and your pup. I am currently a stay at home mom. After dropping my kids at school I am available from 9am to 12:30 pm. If your fur baby is friendly around children I can also be available for walks and drop ins between the times of 1pm to 2:30pm. I would love to chat more to discuss availability and your needs. For drop ins, please let me know what your dog requires and I will make sure they receive everything they need. I am here to put your mind at ease and to make sure your fur baby feels loved and cared for while you’re away!
About: I’ve assisted with dog sitting alongside my mom and grandma, helping with playtime, and companionship. I’m patient, attentive, and following routines to ensure dogs feel safe and cared for. Pet care fits easily into my daily routine. I have flexible availability as I am unemployed and already care for my own two cats and two bearded dragons daily. I provide attentive care in peoples homes, following routines closely. As an owner of two cats and two bearded dragons, I’m experienced with safety, cleanliness, and gentle handling.

About: Animals have been a part of my life for as long as I can remember! I grew up surrounded by cats and dogs, and over the years, I've gained hands-on experience caring for animals of all ages, breeds, sizes, and personalities. My experience goes beyond everyday pet care. I've attended obedience training classes with several of my own dogs and worked closely with a professional dog trainer to better understand canine behavior, body language, and the individual needs of each animal. This has helped me develop a patient, attentive approach to caring for dogs with different personalities, including those who may need extra time, reassurance, or structure to feel comfortable. I've cared for puppies, senior dogs, and pets with special medical needs. My experience includes administering oral medications, assisting with post-surgery recovery, caring for rescue puppies, and helping dogs work through separation anxiety. I also have experience providing overnight care for cats, including feeding, playtime, litter box maintenance, and helping a rescued kitten adjust to a new home. At home, I'm a proud pet parent to Nala, my 11-year-old Greyhound/Shepherd mix, and Koda, my 5-month-old Chiweenie! We also share our home with my roommates' two senior dogs, giving me daily experience caring for dogs of different ages, breeds, sizes, and personalities. Living in a multi-dog household has taught me the importance of recognizing each dog's individual needs, understanding their body language, and maintaining a safe, comfortable environment where every dog feels loved and secure. I'm a firm believer that every pet deserves more than just the basics. Whether it's reinforcing their favorite tricks, enjoying a walk, engaging in playtime, or providing extra affection, I make an effort to connect with each animal and understand what makes them happy. I also know how important routine and consistency are to a pet's well-being. When caring for someone else's furry family member, one of my first priorities is learning their established schedule, habits, and preferences so I can provide a familiar, comfortable experience while their owner is away. I will treat your pets with the same love, patience, and attention I give my own! I'm an early bird, usually starting my day around 5 a.m., and I currently work part-time three days a week with a fairly flexible schedule. This allows me to make time for pet care throughout the week and accommodate a variety of schedules. Caring for my own dogs is already an important part of my daily routine, so incorporating walks and drop-in visits for your furry family members is something I genuinely look forward to! I understand that pets thrive on consistency, and I'll do my best to accommodate their established feeding, walking, and bathroom schedules. Whether your pet needs an early morning potty break, a midday walk, or some extra attention and companionship while you're away, I'm happy to discuss a schedule that works for you and your pet's needs. Your pet's safety, comfort, and happiness are my top priorities! I understand that every animal has their own personality, routine, and individual needs, and I take the time to get to know them so I can provide care that feels familiar and reassuring. Before caring for your pet, I'll make sure I understand their feeding and bathroom schedules, medical needs, behavioral tendencies, and any household rules or special instructions. I believe maintaining consistency is especially important when their favorite humans are away, and I'll do my best to keep their daily routine as normal as possible. For pets who may be shy or anxious, I take a calm, patient, and confident approach. I never want an animal to feel pressured into interacting with me. Instead, I give them the space to observe, explore, and approach me when they're comfortable, allowing trust to develop naturally. I'm also comfortable following detailed care instructions, including administering medications when needed. During walks and drop-in visits, I'll remain attentive to your pet's behavior, comfort, and surroundings to help ensure they have a safe and positive experience. And one of my favorite parts of pet sitting? Sending photo updates! I love capturing those little moments that let you see what your furry family member is up to while you're away. You can expect regular updates and photos so you can enjoy your time away knowing your pet is in caring hands.

About: My sister and I had pets since I was a child. Frogs, fish, turtles, dogs/puppies, bunnies, and a parrot. I would say I am well rounded in pet care. I can watch your furbaby in home if you like. If you need someone to drop in and take care of your pet while out, I am also willing to do that. I know how to administer oral medications if that is of need. I currently have one rabbit and a lab. Making your pet comfortable and happy is what I strive for. I am currently working from home so I have more than enough time to take care of your animal. I will be available to feed , and do any extra activities that your animal may need. * I do home stays but I will not stay overnight I can stay all day and leave super late but I can not stay overnight. When in your home if you have schedule that you like me to follow I can do that. I like to just have fun play,give cuddles, and for some dogs like like to be lap dogs I can do that too.
About: Where do I begin? I’ve had dogs since the time I came out of the womb, but I officially received my own baby at the age of 6. Our family loves dogs, as there has never been a time we had less then 2-3 dogs in our house. Right now I have 3 dogs and I love them more then anything. They are inside dogs and I wouldn’t have it any other way! All of my dogs have always slept with me in bed, but it could be due to me being the one who feeds them lol. My passion is to love and care for all dogs! Being a vet use to be my passion, but I could not bare to see a pet go! I love dogs more then anything and any chance I get to pet one that passes by, I will take! I hope to have the chance to meet as many dogs as I can through this site as I will love on them as if they were my own.
About: I’ve been around dogs my entire life, and for the past 13 years I’ve been consistently caring for my own pups. Over the years I’ve worked with just about every breed you can imagine: Terriers, Huskies, Dobermans, Pitbulls, Boxers, Chihuahuas, Yorkies, Labs, Schnauzers, Poodles, Pomeranians, Border Collies, German Shepherds, Great Pyrenees, and more. No matter the size, age, or personality, I love getting to know each dog and what makes them happiest. At home, my wife and I share life with two Huskies and a cat, who we treat like our kids (yes birthdays and all!). Because I know how important our pets are to us, I extend the same level of love, patience, and care to every pet I look after. I come prepared with tandem leashes, a pet stroller, and standard leashes for walks of all kinds. I always pick up after your pup and make sure they’re safe, comfortable, and enjoying their time outside. For peace of mind, I’ve completed First Aid & CPR training (through both college and my career), and I stay up-to-date on general emergency response. While my certifications are human-focused, my training has given me the ability to quickly assess situations and take action; whether that means recognizing signs of overheating, making sure hydration is available, or adjusting for temperature and activity levels. I’m also OSHA certified, which means safety and awareness are second nature to me. Your pets will be in caring, capable hands, and I’ll treat them like my own from the moment we meet. I currently work a full-time government job. My wife is a teacher, so our lives are pretty busy. I am looking to do this as a part-time and enjoy combining a few things I enjoy: pets and exercise. Current Schedule: I get up around Noon, on the days I work (Wed, Thurs, Friday, Sat, Sun) I work from 6PM to 6AM. I will only accept care appointments between 1PM and 4:30PM. On Monday and Tuesday I will accept care appointments between 1PM and 6PM. Currently boarding is off the tables since my wife and I are busy. But I can make drop-in visits! In my home, pets are treated like family. I make sure they always have access to fresh water, healthy food on schedule, clean bedding, and plenty of love and attention. I keep playtime safe but fun, and I’m mindful of the temperature, hydration, and overall comfort of every pet in my care. My own pets get birthday celebrations, vitamins, and daily exercise, and I extend that same level of care to visiting pets. In a client’s home, I respect your routines and follow instructions closely so your pet feels secure in their familiar environment. That means sticking to feeding schedules, cleaning litter boxes or outdoor areas, refreshing water bowls, and making sure walks, playtime, and cuddle time happen as you prefer. I also handle clean-up (messes, accidents, fur, or litter) so your home is just as you left it. My goal in either setting is to keep pets happy, healthy, and comfortable while giving you peace of mind knowing they’re in capable and loving hands.
About: I've been around dogs with different backgrounds my entire life and started taking care of them at the age of 10. I have experience with light grooming (Brushing fur) as well as brushing teeth. With cats I have experience feeding and playing I have many friends with cats that I visit often. I take care of the pups at home all the time. I feed them twice a day and make sure to brush and groom once a week. And I also enjoy taking them on walks to the dog park. At my house I allow the dogs to free roam as they are potty trained and use the backyard. I make sure to keep anything they could swallow out of reach.
About: I provide dog sitting in your home, also dog walks and light grooming. I guarantee I will supply the best energetic, companionate, loving and safe environment for you and your furry loved ones. I have over 13+ years experience house sitting for families. I have always been in love with animals at such a young age. I am very passionate about animals and will do everything possible to help them in anyway shape or form. I would honored to be with your loved ones. Like I say dogs aren’t just a mans best friend, they are way more than that, they are family. I do work at the school district & I do have commits for my church but I have my schedule in advance. I am very opened to speak in more details and get to figure out the best routine together. I do communicate prior to any bookings. I do currently have a dog her name is Luna and she loves dogs and people, even kids. She has lots of energy to play.
About: Pets of all sorts have been a part of my entire life. From bunnies to leopard geckos, Guinea pigs to tortoises, the list goes on! I’m the oldest in a large family so I’ve learned and perfected responsibility from a very young age. I will take care of your pets as if they were my own. From the plentiful amounts of petting and cuddles to walks and dog parks if preferred, I do it all! I’m a stay at home mom in an active duty military family and enjoy helping families wherever and whenever I can. I can’t wait to meet you and your fur baby! I am currently a stay at home mom and have been for the past 6 years. Therefore, I have plenty of time to devote to your precious babies, since I’m always home! I have a turfed yard which is fenced and can allow your pet free in and out access if needed. I have the necessary space for crates and can provide one if your pet should need it throughout the day for naps or at night for bedtime. I provide daily morning and afternoon walks and don’t mind pampering them with a spa day! I have one dog named Kiké who loves to have play dates and knows how to play extremely well with dogs of all shapes and sizes! Whatever your needs are, just let me know and I can definitely adjust!

About: I’ve owned dogs my whole life and have been around all types of dogs. I have patience and compassion for whatever dog I come across. I’m a college athlete and commuter. My afternoons are completely pilled up with classes and training sessions. I’m looking to earn a couple bucks in the mornings to help with books and tuition. I’m always open to learning more and seeking more perspectives. What works for some people might not work for others so I will always be open to listening to how you would like me to care for your dog. I can be flexible as possible and always will try to help in any way possible.
About: I treat every dog like they’re my own. I’m patient, calm, and tuned in to each pet’s unique personality and needs. I have experience with both puppies and senior dogs, so whether it’s helping with basic training, keeping up with high energy pups, or providing gentle care and routine support for older dogs, I’m confident and comfortable doing it all. I pay close attention to behavior, body language, and comfort levels to make sure every dog feels safe and understood. I’m reliable, communicative, and I always go the extra mile to make sure pets stay happy, healthy, and stress-free while you’re away. Pet care fits easily into my daily routine. I currently work a part-time job, which gives me plenty of flexibility and time to give your pets the love, attention, and consistency they need. I plan my schedule around feeding, walks, playtime, and check-ins, so each pet gets dedicated care throughout the day. Whether it’s daily visits or longer stays, I make sure your pets feel safe, comfortable, and loved with a steady, reliable routine. When I’m caring for pets in a client’s home, I focus on keeping their routine as familiar and stress-free as possible. I follow your instructions closely, feeding schedules, potty breaks, walks, meds, crate time, and any house rules your pet already knows. I give plenty of attention, playtime, and check-ins so your pet feels safe and comfortable in their own space. At my own home, I have four friendly dogs, so visiting pets are welcomed into a social, loving environment. I make sure everyone gets along safely, and I supervise all interactions to keep things calm and positive. Your pet will get lots of companionship, enrichment, and affection while they’re here. No matter the location, I keep water bowls full, maintain a clean space, and send regular updates and photos so you always know how your pet is doing.
About: I’ve always loved and cared for dogs, even as a kid I volunteered to watch dogs for family members and friends. I get down to the dogs level to let them explore my scent and see what I look like. I like to carry healthy dog treats for when they don’t fully trust me because trust is important for me and I want to make sure they know I’m not a threat and just a friend I’m currently working a full time job so I am only available to watch doggy’s on Tuesdays and Wednesdays unless I’m needed longer I can accommodate Safety and trust are my number 1 priority, it’s important to me to let doggy get to know my scent and on day one I mainly focus on letting them know I am a friend rather than a caregiver so they know they can trust me and get excited when they see me
About: I’m a stay at home mom of an older child who now has the time to help my neighbors care for their fur babies! I have had dogs all my life and grew up on a dairy farm. I am truly an animal lover and feel like life isn’t complete without a furry companion to love. Currently have one 10 year old Jack Russell Pomeranian named Charlie bear who has medical needs and two cats! Big kitty and applesauce. Charlie needs medicine for seizures so I feel comfortable with administering medications. I would love to be able to provide you with the comfort in knowing your animals are well cared for and looked after while you’re at work, vacations or other activities! I’m a stay at home mom of an older child that has a lot more flexibility than before. I can be available most times during the week. My house is geared towards my animals. The cats have a catio and tunnel all around the backyard so they can be outside. My dog goes on walks twice a day in the park but mainly prefers to be in my lap.
The median cost per walk for dog walking in Winchester is $25
Dog parents share their Rover experiences - Winchester
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- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
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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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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 - Winchester
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester average 3 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost of Dog Walking in Winchester is $23 per walk as of October 2026. Most bookings cost between $22 and $29 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 3,471 sitters on Rover offering Dog Walking across Winchester. 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. 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 , 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 Winchester 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 , 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winchester. On Rover:
- 88% of walkers can help with special care needs
- 91% 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 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 .
walkers on Rover set their own , 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.

