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

Over 2 pet parents in Winchester have booked dog walking
Winchester, 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 am available for all holidays, even on short notice. I'm also more than happy to check in on your kitty, scoop the litter box, and chat with your kitty while she hides behind the sofa. Lol I worked as a vet tech for about 10 years. I always felt like I had my dream job! I took care of older very sick pets, diabetic pets, pets that had chronic health conditions. Whatever special attention your beloved pet needs, I can provide that. There isn't much I won't do to keep your pets safe and happy! I think our pets are more precious and special than we could ever put a value to it! Just let me know what you need. I can come to your home as many times a day as you need. Or just stay there during the day....... whatever works for you. I work during the day, so if your pet has extreme separation anxiety, I might not be a good fit. But I am available for check-ins. I have a large chain link fenced yard and an automatic doggy door. This is not a "kennel". While your dog(s) are in my home, they will be part of my family. I will play with them, give them hugs, I will talk "baby talk" to them, cuddle on the couch with them while watching movies.

About: Hello!! I have two cats a beautiful Red Calico and a Siamese Mix as well as a Bordercollie Mix puppy. I have grown up with cats and dogs and would love the chance to help out the community! I am currently working part-time in this economy its hard to make it on one income, so why not do something you enjoy on the side? I have an enclosed back porch that all animals enjoy! My cats have a inside door to go in and out as they please and puppies go out for supervised play time.
About: I provide a large area to play and toys and activities to engage in for wonderful fun. I have plenty of places like trails to walk them.I groom everyday to keep maintenance and beauty. I give out lots of love and attention to make each feel special. I have had dogs for about 24 years and have provided care for some over the years. I know how to handle emergency situations when it comes to dogs. I have groomed many bigger dogs like great pyrenees and as small as yorkies. I have 1 dog of my own that is healthy and happy and are willing to make this love for my dogs as well as others, a full time job. I look forward to providing helpful services to you and your dog. I'm currently working part-time, so I'll have plenty of time to play with your pups and give them lots of attention to make them feel right at home I have a fenced in play area and a large farm for them to enjoy on leashed walks. I can easily crate your dog if needed if they need a safe place to adjust to the new environment.
“I am so thankful for Shannon! She gives my pup the quick exercise that she needs while I'm at work. She's very easy to communicate with and sends me great updates! My furbaby loves her walks with Shannon.”

About: I have grown up in a home full of dogs as long as I can remember. I have raised dogs as puppies well into their adult lives, and been blessed to be with them through their last breath. I cannot imagine a life without my pups! I will care for animals of all ages and be sure to treat them with as much love as I do my own. I am currently working full time - my availability will be before 7 AM and after 4 PM Monday through Friday. My weekend availability is completely open! I have two dogs of my own and I am currently fostering another pup whose parent is in the hospital. I am able to travel to your home to care for your pet and ensure their needs are met, whether that’s cuddling up and getting belly scratches or playing fetch!
“I can’t recommend Gabby enough as a dog walker! She’s absolutely fantastic with my pitbull, Mabel. From day one, it was clear that Gabby truly cares about dogs. Mabel is energetic and sometimes a little stubborn, but Gabby always knows how to keep her engaged and well-exercised. I love how attentive she is to Mabel’s needs—whether it’s adjusting to her mood or making sure she gets the perfect amount of playtime. Gabby is punctual, reliable, and incredibly professional. It’s so reassuring knowing that Mabel is in such great hands every time Gabby takes her for a walk. I truly appreciate how Gabby goes the extra mile, even providing little updates and photos of their adventures. If you’re looking for someone who’s kind, trustworthy, and great with dogs of all kinds, Gabby is the one!”

About: I am friends and families go to dog sitter for when there is vacations, or someone is busy. I have been doing this for family and friends for a couple of years now im currently college student and would love to watch over your fur babies! with me being in school and work i’m normally pretty flexible with my schedule as all my classes are early in the morning! I have a huge fence around my yard and two adorable fur babies if yours are needing some company. I will be able to watch over your dog at all times if needed.
“Mike was awesome! I received pics of Chaos walk and updates He was a good match for my strong dog.and handled him amazingly. I would definitely recommend for all dogs He went above and beyond for Chaos Thank u Mike”

About: I have been a dog lover since I was a small child. I was raised with dogs, cats, ferrets, fish- you name it! Lol. I actually own three dogs of my own! I have a 2 1/2 year old little girl named Aila and I am currently a stay at home mama. My husband and I take them on tons of adventures whenever we can and spoil them rotten. I have a lot of experience with all different kinds of breeds and have rescued most of the dogs in my life from local shelters and rescues. I have a lot of respect for animals and find them to be the most intelligent and resilient creatures. I adore being around them. I have dog sat many times over the years for people. I figured why not add some variety to my life! So, I decided to join Rover! 😍 I treat every pet that comes through my door, like my own. I provide fun extras too. When I board dogs in my home, on their last day they get treated like they are at a spa. Every dog gets a pup cup! I also spray them with pet deodorizing spray and give them a greenie so they go home smelling so nice. I have extra crates and dog bowls that are all thoroughly sanitized between dog visits. I usually just ask clients to bring a favorite toy and or dog bed if they want to. It helps with separation anxiety. If not I have lots of extra dog beds and dog blankets. People usually board their dogs because they can’t take them with them for work trips or vacations, so I like them to feel like they are on vacation too! I am currently a stay at home mama so I have a lot of availability including overnight pet sitting in my home. I can do anytime during the week and on weekends as well! I book a lot of clients over holidays too! My daughter also loves to help me care for the dogs. I have been teaching her about dog care and respect for animals since she was very young. She loves every second of it. She even helps me take them outside to play and helps me prep for feeding time too. She knows to respect animals and give them space when they need it. But to be honest what mostly ends up happening is she watches tv with them and they snuggle so much and have snacks :) I have a fenced in back yard in a very safe and dog friendly community. My dogs also love other dogs very much! We have lots of fun dogs toys and love to stay active. I can vary the activities we do based on your pets needs and wants!
About: Hi, I’m Sarah, a lifelong animal lover with years of experience caring for both dogs and cats! Growing up surrounded by pets, I learned early on how to provide the best care, love, and attention to furry family members. I’m the proud dog mom of two incredible pups: Stella, my energetic Labrador, and Hank, my playful Corgi. Raising them has given me firsthand experience managing high energy, playfulness, and ensuring their health and happiness. Alongside my experience with dogs, I’ve also cared for my father- and mother-in-law’s cat and my sister’s cats while she’s been away. These experiences taught me how to meet the unique needs of cats, from feeding schedules and grooming to providing a safe and comforting environment. In addition to my passion for animals, I have knowledge of basic medical care, including recognizing signs of illness, administering medication, and supporting overall health for both cats and dogs. Whether it’s playtime with pups, snuggling with cats, or maintaining routines to keep tails wagging and whiskers purring, I treat every animal as if they were my own. Let me help care for your beloved pets—they deserve nothing but the best! 🐾 Hey neighbors! As a full-time pet caregiver, I absolutely love what I do! I do have a wonderful pack of my own dogs to care for at home, which is why I truly appreciate advance notice for new bookings so I can coordinate everyone's schedules perfectly. 📅I am always happy to help out with morning, midday, or evening visits whenever things align! You can count on me to bring lots of positive energy and ensure your furry family members get all the love, undivided attention, and top-notch care they deserve! Can't wait to meet your pups! ❤️ Caring for my own pups, Stella and Hank, has taught me the importance of maintaining a consistent routine to keep them happy and healthy. They thrive on their set schedule, which includes two daily walks, either on my street or at the walking track near my home.We also spend quality time playing in the yard. My dogs love meeting and interacting with other animals, and I always ensure their time is filled with exercise, play, and lots of love.
About: I love volunteering at the shelter, helping foster when needed, and I love always having my own two babies to take care of, which is such a joy inside and out! Helping neighbors, friends, and family has always been easy for me! I’m currently working part time, so playing with your pups will be no problem for me! I am available anytime every other week, and available anytime before 5 am and after 5 pm on the other weeks! I also have free weekends as well! I have my own two little guys who I treat like my babies. They sleep with me, walk with me, go with me almost everywhere, and I make sure not only are they taken care of but also my clients. I can do as needed, and provide what my pet parents need and want! I have no hesitation for any pets, I love them all!
About: My name is Hannah, but I go by Mikki. I have had pets since I was 15 years old and they have ranged from cats, dogs, and the exotic! I have a serious love for all the different types of fur-babies and am a proud pet parent myself! I’m the purrfect fit if you love someone enthusiastic about animals and their care, someone who is strict with rules and restrictions, and someone who is flexible! I have worked in a pet boarding type facility in the past and carry much experience wrangling dogs of all sizes and in all group sizes, with all different types of personalities. I also have a dog and cat myself. My daily schedule involves me waking up and letting my dog out while preparing their breakfast. After they eat, we get some snuggles in until it’s time to go potty. Later on, it time for dinner and then a nightly walk 30 minutes to an hour after dinner has been served. That ends our adventure for the day! For Drop-Ins: I stop by for feedings and enrichment for between 30 minutes to an hour. I make sure they care squared away and everything is locked up before I leave. For Walks: It’s simple … we just go for walks. 30 minutes to an hour or whatever set path and time per appointment. For House-Sitting: I set a time for me to come over. I stay for the duration of the appointment set and bring my own necessities so that I don’t have to leave the premises. I stay within your home, where your babies are most comfortable, and provide them with company and a set schedule. Before I confirm a booking, I will ALWAYS set up a meet-and-greet. I need to be able to sit down with the fur-babies and parents so we can get a good view of the vibes and to see if I would be a good fit. These meet-and-greets are NOT OPTIONAL and refusal will result in a CANCELED BOOKING! Sitting should be a comfortable experience for pet, pet parent, and sitter. Checking the vibes and getting details is critical for success.
“Melanie took excellent care of our two puppies. They got a good walk and she played with them. She is dependable and trustworthy. She will always be our trusted caregiver when we are away.”
About: Hello my name is Shantella, I am available to dog walk and to pet sit. I have experience looking after dogs, cats, hamsters and rabbits. I am available to walk pets Tuesday-Friday. I can pet sit Monday- Sunday Please let me know if you have any questions about my availability I can care for pets in your home or mine. I have a fenced in yard, I have a 1 dog and 1 cat, I can take your pets on walks and follow care instructions provided.
About: My name is Luke, I am a CATCH Canine Trainer Academy certified dog trainer. I use positive reinforcement to encourage and maintain behaviors. I have always had a passion for working with dogs but after losing one of my rescues to cancer only 2 months after saving her my passion grew. This had inspired me to help owners and their dogs learn and grow together. I am a Co owner of a food truck which we are only operating part time. On the opposite days I have open availability to help support you and your current fur baby. I am unable to offer boarding for animals at this time. I am certified in pet cpr and first aid through ProPetHero by Pro Trainings
About: My name is Kayleigh and I absolutely adore animals! I’ve loved and took care of animals since I was 7 years old. I’m looking to become a veterinarian in the future. I’m going to college to become one! What will set me aside from everyone else looking to care for your pet is I will treat your animals like I treat mine & mine to me are family, meaning i will do anything I can possibly do to help your animals, care for your animals, and make them have a good time. I will constantly show them attention and affection. Whatever your dog needs I will definitely take care of it! I hope you guys pick me to love your animals. I am always able to work with anyone’s schedule. For boarding and daycare their is always someone at the house with your pets. Drop ins and house sits are very easy for me to accommodate my schedule around as well. I have a fenced in back yard, most of the time we could be inside playing with toys, snuggling, or we could be outside playing with my two dogs marley and mowgli. They will be supervised at all times. & i also send pictures just to ease the worries.
About: I have many years of caring for pets and ran my own kennel in Florida for about 13 years and was a Vet technician for 8years I’m available weekends and can also be on call if needed. I can also be available on some Wednesday’s and holidays I’m open to any times I will care for your pet as if they are my own fur baby and will provide what is needed to take the best care of your pet
About: When I was young I used to accompany my aunt to her pet sitting jobs, my favorite gig she had was taking care of three dogs: Harley, Kramer and Jax. Two Minature Schanuzers and a Jack Russell Terrier. My only recent sitting job was feeding, scooping litter, giving pets to 4 friendly felines and 1 cute dog named Luna. Luna had a 6 step feeding regiment and was at first very unsure of me being a new person, but I quickly gained her trust. I'm currently taking time off from working so I have complete open-availability. Monday - Sunday 24/7 365. If I'm needed and I don't have any withstanding appointments, I can be there. I have too many pets for a comfortable home-stay, but I'm always available for a quick visit or single day or multiple day visits. I could probably stay full time at someone's residence if needed. I always double, triple check that a key is hidden or placed well. I'm very attentive using doors, checking multiple times if I lock and watch the doors going in and out. I can follow very specific feeding or diet instructions if needed.
About: I’ve grown up with dogs, cats, horses, you name it. Animals are underrated as members of the family in my opinion and I just want to make sure any animal in my care is treated like family. I take care of my animals (two dogs and a kitty cat) daily and they have a pretty set routine, I would be working my schedule around their routine and working on my days off. I’m happy to drop in and check on your babies and give them love and attention on long work days. I know how stressful it is to be at work knowing your baby is alone at home and I’m happy to help!
The median cost per walk for dog walking in Winchester is $20
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?
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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.
Meet local walkers who will treat your dogs like family

1. Search
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Popular requests for dog walking - Winchester
Select a filter and find qualifying sitters offering dog walking.Sitters in Winchester average 2 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost of Dog Walking in Winchester on Rover is $44 per walk as of September 2026. Most bookings cost between $44 and $44 per walk. 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 September 2026, there are 85 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 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 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 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 sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a 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.

