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: I grew up on a ranch and have been surrounded by animals of all kinds all my life. I have a lot of experience with small to large dogs, cats and more. I also have experience administering medications. I have a 15 yo Maltese dog, a year old rabbit, and two roosters that are spoiled and like my own kids. I have had many animals over the years. They all get a ton of TLC, and so will your pet. I look forward to keeping, getting to know and loving your pet as mine. See you soon. I work night shift three days per week. Therefore, my schedule may vary but I would be able to care for your pet in the morning after work, and on my off days. I will be as flexible as possible to make sure I meet your needs. I will care for your pets in your home, or mine, per your instructions and their routine to ensure they are comfortable, and feel secure. I will also play with your pet outside and take them for walks if able to provide them with exercise they need, and to give them some additional attention. I can crate them as needed per your instructions, and clean up after them as needed.
About: I have taken care of dogs since I was a little kid, and theyâve always been under the most perfect love and care for so long. I also always make sure they are always happy and beyond. Usually I like to spend time with them and have fun with them a lot, such as playing with them. Usually Iâm good with dogs, even when approaching them. Itâs very important I understand more about the dog though so I can be friendly with it. I have also done a lot of dog-sitting for my friends who have dogs and cats, and usually their dogs and cats would love me and feel comfortable around me. Iâve also watched over my momâs friendâs dogs a lot throughout my teenaged years, and they would always end up being just fine and happy! Iâd play with them and give them the love and affection they deserve. Iâm currently a graduated student from high school who is going to Tulsa Community College for musical theatre and acting after the summer ends, while I also do work a part time job at a restaurant. But Iâll definitely be free a lot to spend time with a dog and play with them and watch them, or even walk them! I always enjoy hanging around dogs and even getting the chance to spend time with one and make one happy. Never will it ever become a problem for me to watch over one at any days of the week. And if it does that will be a rare occasion, but it always important Iâm given a week or 2 week notice! (Preferably 2 week notice) then I will definitely be more free. I take good care of my 4 cats in my home, by spending time with them, feeding them, playing with them, giving them love and affection, as well. Iâve also taken good care of my 2 dogs throughout most of my life before they passed away recently. Iâd always play with them, make sure they stayed well fed, and I always spent a lot of time with them, making sure theyâre fine. I would also dog-sit my friendsâs dogs and my momâs friendâs 2 dogs a lot as a teenager growing up, which I still sometimes do to this day. Even when not dog-sitting, at my friendsâs house Iâd always come off as friendly and nurturing to their cats and/or dogs a lot, and it would always work usually. But as long as the owners of the other cats or dogs tell me how theyâre like and how they take to new people approaching them, Iâll be just fine and be fully capable of approaching them well.

About: Iâve always taken care of pets whether they were mine, or someone who needed a sitter for the weekend! Pets are our babies as well! Iâm currently between jobs, and have more than enough time in my life right now, and would love to take care of your fur babies! We have 5 acres for them to play on! I have two of my own dogs, who are little social butterflies. They would gladly take on some new friends!
âOmni responded very quick, which was super helpful since I needed someone to check on my puppy dog so last minute. Thankful that my puppy got walked late at night/while it was dark out! Iâll be scheduling with omni again!â


About: Iâve had dogs my whole life and Iâve helped my family take care of dogs when they traveled. Now that Iâm in college, I would like to continue my passion for dogs by helping families in need of reliable and loving pet care. I will treat your pet like my own. Iâm in college at the University of Tulsa. I have classes Monday through Friday but lots of free time during the day between classes and on the evenings and weekends. I live at home with my parents and their dogs. I will need to care for my clients pets at their home. I will follow the clients instructions first and foremost. I will spend a lot of time with your pets walking, feeding playing fetch, petting them, etc. Iâm also happy to do household chores.
About: I resigned from a 14yr career I have been a technician and receptionist for veterinary medicine. SNHU student for anthropology currently online. I love all fur babies As I said before I'm currently an online student for anthropology I'm also minoring in psychology. So I can work on my school work around whoever I am working for schedule as long as I have Wi-Fi I'm good I currently have two dogs and four cats. My daughter used to say I was Dr Dolittle to all her friends although I'm not a DVM and never have been. I literally talk to them like they're humans and they understand what I'm saying
About: Iâve trained 3 dogs to be pet pals. I have had and cared for dogs my whole life. I have cared for puppies to senior dogs and have experience administering medication to elderly dogs. I am currently in college so I have plenty of time to care for pets! I am available to house sit or walk dogs as needed! I am able to crate dogs if needed and have experience dealing with multiple dogs. I also have experience with food aggression and other special needs.
About: I have experience with all types of animals, mainly dogs. I have three fur babies of my own, so I completely understand the feeling of guilt and worry when you have to leave them home. All of my babies are pretty big, so rest assured I am comfortable handling bigger pups. I have dealt with new born puppies and senior dogs, so I am able to meet all your needs. Relocating to Tulsa and looking to build up my Rover bookings again. I'm not currently working which leaves plenty of time for me to tend to your babies! Currently I do not offer any services in my home. I have four dogs that are adjusting to a new home. With that and the unpacking process, I do not feel that it is safe for your babies or mine.
About: Hello! Let me help you and your pet feel safe and secure. I've been a pet lover for years and now have the time to offer care on a larger scale. In the past I have fostered animals, primarily cats and dogs with the SPCA. During that time I worked with small and larger breeds of various personalities. I have the patience to work with dogs that may be anxious or shy, and dogs that are more rambunctious as well. I love learning about animals, and would even like to become a dog trainer. Let's connect! My schedule is flexible and open at this time. I can work mornings, afternoons, or evenings, and I'm always open to discuss what needs you may have. It's essential to build a relationship with the pet. You want the dog to feel secure, ensure that you can change behavior if needed, and pay attention so that they don't find themselves in trouble.

About: Iâve been taking care of animals for as long as i can remember! We got my childhood dog when i was 3 and I took care of him myself til he sadly passed at 15. I also have taken care of many different types of cats and dogs and have my own kitty named mikel! I recently quit my serving job, so iâm available everyday all day! Your pets deserve the best 24/7 care and Iâm here to provide that while your gone! Iâd appreciate a list of vets/vet phone numbers, favorite walking spots, and any other info or preferences! Iâd love to make your pets as comfortable as possible and help you relax while your gone knowing your babies are getting the best care!

About: I got my first dog in elementary school, and ever since then Iâve never had less than two pets at a time. I often bring home dogs I find on the street and take care of them until I can find them a suitable home. I have experience pet sitting dogs of both small and large sizes, and am willing to work my schedule around your pups typical habits. I currently have a very flexible part-time schedule and am also currently enrolled in online college courses. This gives me the ability to structure my day around your petâs needs. I volunteer with animals on Tuesday evenings, but if those times collide we can work it out. :) I do my best to over communicate if I notice anything going on with your pet that might be cause for concern. If there is no backyard thatâs okay, I am more than happy to walk pets multiples times a day. If I am staying overnight I usually do a thorough cleaning of the floors before I leave. I am willing to water plants, take out trash cans, scoop litter, etc.
About: hello, I am Amber I worked as a vet tech in a hospital now am full time vet tech student . I have always had a passion for animals, their care along with behavioral and rehabilitation. I am a mom. I have my own animals. Experienced and knowledgeable in what to do in most situations. Responsible, honest and reliable. I plan in the future to eventually become specialized in animal behavior and rehabilitation. I know these pets are more than pets to you and I will treat them as if they were my own. I look forward to meeting you and getting to know your fur children. Thank you for taking the time to read this. Have a wonderful day! I have a huge fenced yard, 3 well behaved md/LG dogs, 4 cats. We have a 13 yr old boy who also has a passion for animals. I have a baby on the way. I attend school for my licensee as a vet tech. I have my own animals to care for them is first nature. Careing for you furry friends will be a delight for me. Honestly I have only pet sit few animals both in my home. I treat them as if they were my own . However I am very knowledgeable on animal behavior.
About: I've taken care of all kinds of dogs since I was 13. I personally have 5 current pets right now. This includes 1 dog 3 cats and even a turtle. I got a degree to be a veterinarian assistant and worked in an animal clinic for almost a year. Right now I am a kennel attendant at a doggy daycare. Where required online training was required. We get a variety of different dogs. Ranging from small to large, young to old, even a few dogs with some medicine issues. I'm currently working part-time. In my free time, I take my son out for walks, so I can possibly bring dogs with me. I do have my own car for transportation. I'm available Monday and Tuesday anytime after noon, Wednesday and Thursday 11 am to 2 pm. Friday anytime before 2:00 p.m., Saturday early morning to 1 p.m., and Sundays free all day. I live in a neighborhood where there is a lot of strays, so when I walk my dog, I carry a spray shield, which is citronella and animal deterrent from Pet Safe. Working at a dog daycare, we get a lot of dogs with some type of medical condition. From clean Bulldogs folds to make sure dogs take their medicine when needed.
About: I have taken care of dogs and cats my entire life and currently parent dogs and cats of my own. Friends and family have relied on me to care for their pets while out of town, let out for bathroom breaks, and spend overall time loving their pets! I currently work full time however, I have availability every day during the day until around 3 pm as well as all day Monday, and evenings Tuesday and Sundays. I have experience with crating dogs as well as monitoring dogs of all sizes while taking on leashed bathroom breaks or bathroom breaks in a fenced in yard

About: I have taken care of dogs for over 5 years for 20 different families. I love dogs and have 2 of my own and have had many before. I have watched all kinds of breeds such as great danes, labradoodles, pit bulls, german shepard, belgian malinois, and many more. I also clean your house in the time you are away so you come home to a fresh home! I usually have classes in the more that I will go to and then come back right after, take the puppers on a walk or play with the kitties and make sure they are fed before class and in the evening, letting them out every hour or as needed. I care for pets like they are my own. I have 2 dogs and 6 cats , I have also had a bearded dragon that lived to be 7 years old. I always try to make them feel like my own and follow the instructions as best as possible.
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 teamâhere to help if you ever need someone to talk to.

Why Choose Rover?
Cashless payments
Book and pay through Roverâs secured platformâno cash or checks required.
Reservation protection
It doesnât happen often, but if your sitter has to cancel, weâll work with you to find a new sitter.
World-class support
Weâre 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
As of July 2026, there are 590 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 dogâs 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 dogâs walk begins.
The Rover Guarantee is Roverâs 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 Justiceâs 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:
- 96% of walkers can help with special care needs
- 96% 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 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.


