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: Im home 24/7 so you need a sitter dog, walker im there 😭 all I do currently is take care of 4 dogs. Always make sure they get their walk so they stay fit, I never over feed, make sure they get their outside play time and nap time I am on it. I currently have plenty of spare time so im very free everyday to go on walks, play take care of a dog whenever needed. Currently do that right now with my own little weiner army all I do all week is take care of dogs. I have 4 small weenies who love to dig and play in the big back yard and i take them on walks every day or every other day depending on their energy. They do mostly love to sleep throughout the whole day and dig.
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 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: Hello, my name is Belinda. I have been a fur mom for 10 years and I truly love spending time with dogs. I’m able to give your dog all the attention needed, and they would never be unattended. Feel free to bring their favourite toys or let them choose from our selection.I have a large gated backyard that your dog will enjoy. All dogs will get plenty outdoor time. My days start early, so drop off and pickup times are pretty flexible. I’m not currently working, so my full time job would be caring for your pet! Flexible schedule and I offer extended stays as well. Only sitting at home I’ve got experience with it all! I’ve also administered medication to dogs of all ages and sizes. lover of all pets, young and old, big and small. ( I DONT ACCEPT PITBULLS). And for allergy reasons I don’t accept CATS We can do walks, hikes, swimming, even to a play day at the park. I Live on the west Side in a house with a fenced yard and friendly neighbours!
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 live in a house in French Valley with a fenced in backyard. I have a 10 lb chihuahua mix named Gigi, a goldendoodle named Pinto Bean and a black cat named Clark. We're a family of four with two small children. About this sitter: I'm Heather. Im a California transplant originally from Illinois. I've volunteered for many different animal shelters over the years including Animal Welfare League, Kauai Humane Society and an exotics animal shelter called Animals For Awareness in Palos Hills, IL where I worked with exotics animals like ferrets, sugar gliders, skunks, wallabies, an alligator and a lynx. I've also held part-time receptionist positions at veterinary clinics and worked as a professional dog-walker. I definitely believe that having a dog as part of your family enriches your life in a way that extends beyond the spectrum possible for most human relationships. Jane Goodall is a huge inspiration. I'm a stay at home mom with two small children so we're home all the time and can customize to our guests needs. Walks can be arranged. Each animal has different needs so we aim to be very flexibleand ready to customize depending on each guest's needs. We have a cozy house with a big yard for the dogs to play in. Pets are welcome on the couch.

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: 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: 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: 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 taken care of all kinds of animals! I have grown up around dogs and have had a dog for most of my life. I am also a behavior analyst, so I have a little bit of background in terms of reinforcement systems :) I work fully remote from home, so I am home everyday. This makes it super easy to care for whatever you may need for that day. Recently said goodbye to my senior dog that I had for 13 years, so now it is just one 6 year old pup. She is spayed and loves to play, A LOT. We have a fenced yard and a lovely neighborhood for walks. She is an inside dog, so yours would be too. I have an extra medium sized crate for use as well. She is a lil princess of the house, we are very dog-centric here! We also have a 1 year old, so if your dog doesn't do great with kids or you're unsure, we are probably not the sitter for you.
About: I’ve walked my old neighbors’ Labrador Retrievers regularly a few years ago, walking them both at the same time sometimes. Also I am an excellent dog trainer and dog whisperer. I can walk your dog anytime between 11AM and 5PM Mondays through Thursdays and anytime between 11AM and 3PM Fridays. I can walk your dog for up to 45 minutes at a time, just provide water and poop bags for your dog please. My dog is staying at my Mom’s house out of town. She gives him breakfast in the morning and dinner in the evening. She and my brother take him on 3 walks total per day.
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 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.
“Mark and Carolyn are excellent dog borders caring, flexible and very professional the only people I would consider using for my baby. If you’re looking for inexpensive but the best quality these are the guys to use. Thank you again Mark and Carolyn and I look forward to seeing you again soon.”

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.
About: I will be available during the holidays. Please let me know your dates and needs and I will be happy to work something out. Had dogs all my life and cared for them in all sorts of situations; medications and therapy walks. Monitored them after surgery and held them down for medications they hated. Walked them, ran with them, biked with them and laid down with them. I enjoy animals and I want to spend as much time as I can with them. I will CARE for your pets. They will have fun while I am there. When I had my dog I had a fenced yard with a doggie door for access to the house. I sat with him during thunderstorms and took care of him after ACL surgery. We played ball three times a week or more. He endured my short lived biking phase. He loved the convertible and hated the sedan. I think of him every day.
The median cost per walk for dog walking in Winchester is $25
Dog parents share their Rover experiences - Winchester
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 - 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.


