Dog Walking Winchester
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
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: Hi, I’m Sarah! I’m 18 and I’ve loved animals for as long as I can remember. I grew up with dogs and cats, and I currently have four dogs and one cat of my own, so I’ve always been around animals. I work at a dog daycare in Lawrence, where I get to work with all kinds of dogs. I help with playgroups, feeding, medications, and making sure everyone is safe and doing well. I’m also comfortable with cats, including cats that are a little shy or like to keep to themselves. I recently graduated high school and just started at JCCC. I’m taking my prerequisites there and hopefully will eventually transfer to K-State and continue working toward my goal of becoming a veterinarian! My boyfriend, Cameron, is 20 and helps me with pet sitting. He loves animals too and has a lot of experience with them. He helped train our German Shepherd from a puppy and grew up with several cats, so he’s comfortable around both dogs and cats. I just like to let everyone know that Cameron may come with me for visits or overnight stays. We both really enjoy being around animals and will take great care of your pets while you’re away! I work Tuesday through Friday from 7:00 AM to 6:00 PM, but I’m available before work, during my breaks, and after work. So I am able to check your pets every 4-5 hours. I also have full availability on weekends and Mondays. I do my best to be flexible to meet your pet’s needs !! When I’m caring for your pet in their own home, my goal is to keep their routine as normal and stress free as possible. Whether that’s feeding, walks, playtime, medications, or plenty of cuddles, I’ll make sure they get the attention and care they deserve. I know how important it is to trust someone with your pets, and I treat every animal as if they were my own! I’d love the chance to meet you and your pets! Feel free to reach out with any questions or to set up a meet and greet.
“It was truly a pleasure to have Alyssa walk our girls on a regular basis. She's responsive, flexible, but above all, reliable. We thank you for being an outstanding Rover!”
About: I’ve worked professionally in animal welfare for two years. I’m a certified pet sitter for both dogs and cats while also being pet first aid and CPR certified as well. I’m also fear free certified. I’ve owned my own dogs and cats for the last 10 years! I currently work part time in animal welfare. I’m able to come to your home Tuesday, Thursday or Friday anytime in the afternoon after 12:30. I can come to your home and walk your dog for fresh air and exercise or I can do a pet visit where I check on your dog/cat! In the comfort of your home I can let a dog out to their yard, feed/water cats or dogs, play time etc
About: Animals have always been a huge part of my life. I grew up caring for dogs, cats, horses, goats, chickens, and turkeys, which gave me hands-on experience with animals of all kinds from a young age. Over the years, I’ve cared for dogs for family, friends, and neighbors, gaining experience with everything from puppy potty and crate training to feeding, walking, bathing, administering basic care, and providing lots of love and attention. I’m comfortable with pets of all sizes, personalities, and energy levels, and I treat every pet like they’re part of my own family. I'm currently working part time, so I have plenty of time within my days to love and care for your fur babies while your're unable to! I have a fenced yard with lots of other friendly dogs that are always eager to have another playmate! Between crate training, potty training, or walks with your pup I am able and willing to do it all!
About: I’ve been loving and taking care of animals all my life. I’ve loved them since I was a baby. I try to save every stray! I’m retired and looking for something to do that brings me joy and this is it. I’m available anytime during the day and the evening I will be caring for pets in other peoples homes but I have a fenced yard for my babies but monitor their time in the heat and cold.
About: I was always around a dog as a child and grew up knowing what they wanted, when to go outside, when to feed them and make sure they were played with. They can be unbelievable friends and I think they keep our lives actively expanding. I like to work part time and do the dog sitting when ever it's needed. It can be a random cases and I'm more welcoming to act on immediate services needed. I male sure the pet doesn't get into anything. For example: The trash can, anything chemical on the floor and make sure before they come over...if dog is being watched from my home. I make sure to clean up vacuum and make sure it's an very clean environment. Only feed them what pet owners advise me to give their dogs.
About: I have been dog and cat sitting since middle school, so 8 years now! I live in Oklahoma and go to school in Kansas and do Rover in both for half the year. I have a bigger dog and smaller cat of my own at home, but not in Kansas. I volunteer at the Lawrence Humane Society and love all types of animals! I’m currently in school but am available most hours of everyday. I don’t have many other obligations during the weekdays so I am very flexible with timing! I am willing to work with whatever the owner would like. I am definitely willing to spend the night if necessary and can let out however often you would like.
About: My sister runs kennels of all types of animals, i’ve gained so many experiences from her to bring proper care to your (fur) children ! i currently work part time as a barista, and i love animals so much so why not fit them into all of my free time! i have a big fenced yard that we keep clean, i have big pet beds and 3 different watering stations at my house. I am very good at reading animal language and have a certain knack for taking care of animals!
About: "If you can look at a dog and not feel vicarious excitement and affection, you must be a cat." ~Terri Guillemets Love dogs (and animals in general, but dogs especially.) I have been around them my whole life and wouldn't want it any other way. I come from a large, mostly rural dwelling family, my grandma had 11 kids 2/3 of which have at least 1 or more dog(s) including my mom. I've always had my own and/or lived with roommates/friends/family, that have/had dog(s) in every house I've lived from day 1 to the present. Although I can't say I've taken care of every breed out there (doubt that many people can) I have definitely seen my fair share of mutts and purebreds alike; from Corgis to Chihuahuas, Danes to Dobermans, Lhasa Apsos to Shar Peis, and even a couple of wolves (3/4 mixes) as well as a few rodents, cats, reptiles, arachnid and birds. Big or small I love "em all, but if you forced me to pick a favorite I'd have to go with the affectionate yet intimidating Perro de Presa Canario. In short, if either by choice or necessity you find yourself in need of a caretaker for your 4-legged (or more) companion(s), know that I would be elated for the opportunity and you can be assured that their health and well-being will invariably be at the forefront of my mind in all that I do while they're in my care. Thank you for taking the time to read this and I look forward to hearing from you soon. "Lots of people talk to animals.... Not very many listen, though.... That's the problem." ~Benjamin Hoff, The Tao of Pooh
About: My family has had dogs, cats and fish my whole life. I often watch them when my parents are out of town and I have dog and cat sat for family & friends for years. I have helped a friends family with their cattle and pigs, but am not as experienced with livestock outside chickens. I’m currently available 7 days/wk I work as a server in my pleasant so whoever I’m staying with ideally should be able to go 6-8hrs between potty breaks! If I have 2 weeks or more advanced notice I can make arrangements to be able to check in more frequently. o o o o o o o o o o I love interacting with the pets and getting to see them get more comfortable with me. I am very comunicative and willing to ask questions.
About: I’ve been taking care of animals for over 15 years now! I currently have a dog named Hunter and a cat named Harrison! I love animals, so I will make sure your fur baby gets all the loving! Friends and family have relied on me for years, so you know you’re in the best of hands! I currently teach school at an elementary school so I am available anytime after 4:30 during the week! I promise your fur baby will get lots of attention! I make sure everything in the home is neater than when I came in. If the animals make any messes, I always clean it up. I treat the owners home with care and respect.
About: I’m an active adventurous person ready to play with the dogs or take them on walks. I have helped family, friends and neighbors watch their dogs, whether it be just a check in or a week at a time! I work as a phlebotomist in my other times, help family and create crafts for my page! Seeing as I have a cat of my own, I make sure to put her into my daily schedule and make time for her to play with her and her as well as make sure her litter stays clean and her food and water bowl stay full! My cat is an indoor cat. Although she is aloof, she still loves to come cuddle and I always make sure that her food and water bowls are full, her litter is clean and her medicine is taken
The median cost per walk for dog walking in Winchester is $18
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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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Meet local walkers who will treat your dogs like family
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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
As of October 2026, there are 501 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 walkers who have experience with handling special pet needs in Winchester. On Rover:
- 93% of walkers can help with special care needs
- 100% can help with giving oral medications or injections
- 98% 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 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.
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