Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 19 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 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: 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.
“Nicole’s been walking our large energetic dog for a couple months now. She communicates really well and is very active walker! We are always quick to recommend her. She has a very flexible schedule and always sends multiple pictures.”
“Cynthia was amazing- she went above and beyond the call of duty. It’s obvious that she loves animals. It stormed all weekend while we were gone, but she was very careful to make sure that our dog was comfortable. Thank you, Cynthia.”
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.
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 have had a lot of experience taking care of pets! I live on a farm when I am not at college so I know how much care and love animals need! I just recently got a new puppy and I love to care for him! I am currently a student/athlete at Valparaiso University. My schedule is pretty open and flexible and i’m always open to adjusting when I need to! I don’t not currently have a job so i’m usually available whenever! I love spending time with animals! I am very loving and caring. I enjoy going on walks and getting exercise! I able able to care for any type of dog or cat!
“Alycia is so caring and attentive toward my dog. She’s also flexible. When the weather turned too cold for a walk, she pivoted and spent time tiring my pup out with toys in the house to make sure he got to get energy out. We feel so great knowing that we have her checking in on our dog while we are at work!”
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.
“Alli accepted a week before when another sitter cancelled on me …she was so professional booked a meet and greet right away. She took such good care of my babies (I have three and two are older seniors - and one active puppy!) she took amazing pics and never worried about them she is AMAZING”
About: I’ve been a pet lover, especially dogs, my whole life. I’ve had many dogs over the years, small and large breeds. I love them all! I’ve been a teacher for years and am transitioning to retired life. Let me care for your pup while you work. I’m retired from teaching and want something meaningful to do. I love doggies and will help yours stay healthy and happy with frequent walks. Let me help you! I will use your approved leashes or harnesses to keep puppy safe on walks in your area. Dogs will receive walks, supervision and encouragement from me.
About: Over the years I have taken care of so many different kinds of animals. Personally, I’ve had three bunnies, a hamster, a fish and currently have a dog. I’ve learned that pets make life more fun and interesting! I’m currently working part time, so I am available most days. I am usually flexible and I am willing to frequently communicate with you about your pets needs. Pets often have to be at home alone, so I love getting to brighten their day! I think it’s important to give them love and attention because they deserve it and need it!
About: I love all animals all the time, and currently have one pit mix of my own. I’ve been taking care of children, pets, and plants my entire life, and truly enjoy it. I’ll love your pets like they’re my own! I recently moved back to town, and now returned to Rover as a side gig, so I have no recent reviews. I have a very flexible schedule, I’ll work with you! My dog (Bobo) is very high energy, so I’m used to finding ways to keep a dog’s mind stimulated with games and training, and giving plenty of outside/exercise time. I will adapt to whatever each individual pet needs though, including caring for senior or less energetic animals.
“Love that Patricia did a meet and greet prior to our first walk today and my dog immediately fell in love with her. He tends to be a little standoffish with strangers but immediately acted as though they had been friends forever. Patricia walked him today, was kind enough to check on a few things for me, and let me know how he did. I look forward to many more walks with Patricia! Thank you”
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
“This is the second time I’ve hired Amber for dog walking and just like the previous time, she did a great job, She’s very skilled with my senior dog and her visits are usually the highlight of my dog’s day. She’s reliable and efficient, with great communication through the Rover app. I highly recommend Amber!”
“Mason is a very nice guy and Charly took to him right off the bat. Mason took some great photos while they were walking around the neighborhood. I'd recommend Mason to anyone wanting a friendly and caring walker”
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 grown up around pets and taken care of dogs, cats, and rabbits. I’m currently in college and don’t have a part time job, so my schedule is mostly free. I am currently working part-time as a babysitter, and I go to university in the fall and spring, keeping me close to the area at all times. My schedule is very open, so I will be able to spend adequate time playing with and giving attention to your pet! I treat all animals with love and respect, just as I would treat my own. I am flexible, being able to provide care for your pet and open communication for you!
“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.”
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
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 near you
Select a filter and find qualifying Winchester sitters!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 $16.65 per walk (as of July 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 July 2026, there are 2,585 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.
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