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

Over 20 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.
“Alli did an outstanding job of watching our dog for a week. She was always on time and left us great notes after each walk. Most importantly, our dog was calm and happy when we got home - a true sign that our dog was perfectly cared for. We’ll use Alli from now on.”

About: I am a very pet oriented person, having had cats and dogs in my life since I was small. I am empathetic to when pets need extra reassurance and attention and make sure to go the extra mile to make my furry friends feel comfortable and well cared for. I am currently working part time which enables me with a lot of flexibility and free time to meet your pet care needs. Chances are great I will be able to accommodate your pet visit or pet sitting schedule needs so feel free to reach out and let's get acquainted! I prefer to care for pets in their regular home space to limit their stress. I will be careful to follow all instructions and prefer written instructions for pet care and any light home care needs you have.

About: Through my life I have experienced taking care of family pets, from the puppy stage to crossing the rainbow bridge. I often think I love animals more than people. I am currently working from home part time with flexible hours, so I can play with and cuddle your fur babies as much as they want. I can board, pet sit or just walk your dog weekdays or weekends day or night. I have a fenced in yard with one senior dog. I can crate a dog up to 40lbs. We can go for walks if desired.
About: I am a lifelong cat lover with over 20 years of experience ensuring cats of all ages are well cared for while their humans are away. I currently have two cats of my own, and previously cared for a senior cat who lived to be 19. During each 30-minute visit, I will: - provide fresh food and water (and clean up afterward) - scoop the litter box - brush/comb your fur babies - provide playtime and companionship - fulfill additional requests as agreed upon My goal is to keep your cats happy and relaxed so you can have complete peace of mind while you are away. I work from home full-time, so I can visit your home during the time you request. If you choose boarding at my house, I am available for them all the time. I have spare room for your cats if you choose to boarding. Your cats will have a safe and quiet room with window view by themselves.

“Jennifer was able to help me out on a last minute request to walk my dogs as I had to leave town. She walked both my dogs on a short notice and was great with them. Will book again!”

About: As a performer who travels the world by sea, I know how comforting the love of an animal can be and while I’m away I miss that connection so much! I have loved, snuggled, and pet animals around the world and while I’m back on land I would love the opportunity to give your pets the same attention! I’ve had dogs my whole life and grew up in a home full of furry friends. My parents volunteer with Duo Dogs, so our house has always been a revolving door of puppies and big dogs alike. Two of our English Labs are especially sensitive to fireworks and thunderstorms, so I’m no stranger to calming anxious pups with patience, love, and a gentle hand. Whether it’s a walk around the block, a game of fetch, some cozy snuggle time, or maybe it’s your turn to get out and see the world, I’m here to keep your pets happy and cared for while you’re away. My schedule is wide open during my time home-so don’t hesitate to reach out and let’s set something up! Since I am taking a land break, my schedule is very open! I enjoy my time at the gym, but other than that I don’t have many routine commitments. Your pet’s safety and comfort are my top priorities. I offer care in your home where your pet feels most secure and relaxed. I always follow your instructions closely, respect your space, and treat your home with care. You can trust that your pet will be loved, safe, and well looked after while you’re away.

About: I have grown up with dogs of all sizes and breeds. I’ve dog sat for family, friends, and neighbors. I’ve helped train my family’s dogs in the past so if there are any reinforcements or cues necessary on walks I’m more than capable of helping to keep a routine! I’m currently full time graduate student, but I have some free afternoons with plenty of time to walk your pets! I am also flexible to do drop ins for potty breaks and evening feedings. I do not have any pets but I can help care for your pet with walks! If there are specific needs your dog requires such as to be crated after walks I am more than willing to follow any directions for making sure your pet is safe and comfortable!
About: I used to pet-sit. Worked at a day-care a while ago. I've worked and interacted with all types of dogs. I enjoy what I do. I actually get really excited when working with dogs. I know they're a lot to handle sometimes but I feel like they're great fun to work with and they always make me feel better. My favorite types of dogs include Boxers, Miniature Schnauzers, Miniature Pinschers. I like all dogs of all shapes and sizes. I am really into playing fetch with dogs. I also don't mind playing with rope toys. They might tear my arms off but hey! It builds character! I'm very easy-going and I feel like with dogs you have to have a great sense of humor and enjoy the trade in order to work with them. I hope you consider me for some of your services. I look forward to chatting with you over the phone, internet, or in person! Also, I have a sweet little Mitten cat (her name is Mittens). She's a blue tortoise cat with these little white Mitten paws. My father has a black Maltese poodle named Beau... The sweetest dog in the world. I used to live with him and we were the best of friends. We still are. But we just don't see each other as much. That's who you see me with in my photos. I have pretty much open availability. I am comfortable doing overnight visits and morning/afternoon/evening walks. I'm currently in the process of trying to build clientele so I'm more flexible now than I might be in the future. But my long-term goal is to make this a full time 8 hour day. The 8-hour schedule block will entirely depend upon demand though. Whether it's broken up into different times of the day with a break in between or a full 8 hours non-stop, entirely depends upon when clients need availability. The number one most important thing about pet care is communication though. Between the owner and me. The sooner we know things, the better. Your pet's safety, comfort, and routine are always my top priorities. I currently provide care exclusively in my clients' homes because I believe most pets are happiest and most relaxed in their own familiar environment. Staying in their home helps keep their routine consistent, reduces stress, and allows me to focus entirely on giving them the attention, affection, exercise, and companionship they deserve. I'll also treat your home with the same respect and care I would my own. Whenever possible, I love to schedule a meet-and-greet before the booking begins. It's a great opportunity for us to get to know each other, for your pet to become comfortable with me, and for me to learn about their personality, routines, favorite activities, quirks, medications, and anything else that helps me provide the best possible care. I firmly believe that in pet care, overcommunicating is always better than undercommunicating. I'd much rather ask one extra question than make an assumption, and you can expect prompt responses, regular photo and video updates, and complete transparency throughout your time away. While I would be comfortable offering boarding in the future, I currently choose not to because I share my home with a beloved cat. My decision isn't out of concern for her behavior—it's simply because I don't want to bring unfamiliar dogs into her space. By focusing exclusively on house sitting, I can give your pets individualized care in the environment where they feel safest and most at ease, while ensuring every animal in my care is comfortable, secure, and happy.
“Alycia has been great with my dog. He was reluctant to walk with new people after being home with me all summer, but Alycia was very patient and worked on building his trust over their first several days walking together. Alycia is patient and reliable. She provides great updates about how my dog is doing while she is with him. We feel very happy to have found her to help us with daily walks!”

About: I have experience from working at Kennelwood for 2 years and volunteering at the Humane Society. I've always cared and loved for animals and connected to them deeply. I am a college student so most of my freetime is in the afternoons and on weekends. Please understand if I need to study or do homework! I will respect any boundaries you put in your own home. I would be happy to play with your furry friends and make them feel loved even when their owners are gone.
About: I have two dogs in my own and have taken care of numerous different breeds in my neighborhood, along with family and friends. I enjoy taking walks and enjoy spending time with all types of dogs I am currently unemployed for the past 20 years I’ve been raising my kids. Looking for a job! I have a very flexible schedule. I love spending my time with dogs. Make sure they are happy and loved. Feed and make sure they get enough food, water and affection. Most of all exercise love and safety
About: We’ve loved meeting all kinds of dogs through Rover, whatever breed or size, and we’d love to spend time getting to know your furry friend through walks, cuddles, and just being together! We’ve had several dogs over the years from an 11 lbs. Schnoodle to an 80 lbs. GSP to now Oliver, a 50lb. mix of many breeds. (However, he can go two-doors down to my father-in-law‘s house if our furry friends don’t get along.) We hope to meet you soon. Amy currently works mostly from home with a very flexible schedule. We get up around 6AM in the morning and stay up until about 10PM. We’d love to get steps in by taking your pet for a walk! Carl also often stops home throughout the day. Wehave a screened in back deck and also a fenced in area below that is shaded. Your pet can find the perfect place to relax and enjoy, weather pending!
“Fantastic experience! I was worried about leaving my dog so soon after moving him in with me but Cynthia was very caring, attentive to all my concerns and left awesome updates. Will have her back!”


About: Ive been an emergency vet tech and helping hand for 6+ years. Ive had animals my entire life & adore them so much I made a living off keeping them safe & healthy. Your loved ones will be loved in my home & heart. I work long hours but that means I have more days off to help you out. 3 days out if the week i have off & can accommodate your oets here in my home or stop by your house for potty breaks/walks. My yard is fenced in, my animals are very friendly, my teenage son loves animals & hopes to follow in mom's footsteps in vet med.
About: I have always had dogs growing up. I have done fostering and cared for many pets with sitting. I am home to be able to care for your fur baby and let out for frequent potty breaks, playtime, hugs and walks. I am reliable to be here for your pet needs while you are away. Again when I have them, they get my 100% attention. I can be around to take care of all their needs. My home has availability to have more than 1 dog if they are relaxed dog friendly or I mostly do 1 dog at time. Everything is discussed upfront and happy to have any meet and greet. I will go by rules you have at home to ensure it will be same here. IE. Crate, on furniture or no furniture. What foods needs and be sure to follow that all.
About: I’ve lived with my dogs for around 10 years. I take them for walks, feed them when my family needs some help. I have a big dog and a medium sized dog! I don’t have any professional experience but I take care of my dogs often. :) I’m a student at Mizzou, so I will typically be busy until 3pm when I’m in Columbia. When I’m back home in Ballwin over breaks, I should typically be free at all times. I can’t have pets in my home, but in others home I am able to give walks, play with animals, and do anything that’s needed! I love taking care of animals and I’m super careful with them.
“Sam is amazing! She did a great job taking care of my dogs and let herself available even I needed a sitter last minute. Appreciate her a lot and the love she gave to Olaf and Kirby! Will definitely recommend her to other furparents.”

“Excellent. Reliable. Loved our puppy. Went above and beyond. I highly recommend Amy and will use her again as much as needed. She is an asset to your company. I was very pleased with Amy and rover. Very approachable and flexible. She is a keeper for sure !!”
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
Charles was AWESOME! I’ll recommend him everytime.. booked walking for my dog and it was my first time ever hiring a dog walker or using Rovr. I love the updates and communication and photos of my pet. I felt at ease and comfortable. I knew my dog was in good hands. Great service!

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.
Meet local walkers who will treat your dogs like family

1. Search
Browse profiles of walkers near you who offer dog walking
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Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
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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 for Dog Walking in Winchester on Rover is $17.76 per walk (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .
As of August 2026, there are 2,557 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 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.
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. On Rover:
- 93% of walkers can help with special care needs
- 97% can help with giving oral medications or injections
- 97% 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.






