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

Over 105 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.
“We’ve hired Kim a few times to feed and walk our dog. She is very reliable and friendly and takes great care of our dog. The Winchester community is lucky to have someone like Kim to look after our pets :)”

“Lisette is great with my dogs! We have an older dog that she comes and walks and he loves it. We also just got a puppy and she has been coming over in the middle of the day to take him and our older dog on small walks and it’s been great!”


About: I’ve taken care of dogs and cats of all sorts. I grew up with small, medium, and large dogs as well as indoor and outdoor cats. I’ve also grown up caring for animals from a variety of backgrounds- fosters, rescues, you name it. I genuinely love spending time with animals and since I can’t have one of my own this seems like a great way to connect with pets and offer my services. I’m happy to come meet any animals in advance to make you more comfortable. I currently work remotely 90% of the time so this gives me a lot of flexibility to walk and take care of animals during work day hours if needed. I’m very good with following whatever directions will make you and your pets feel the most comfortable in your homes and out on walks.
About: I’ve loved animals my whole life, and I’ve had the pleasure of living with, and pet sitting for multiple cats and dogs. I’ve done both kitty and dog meds, so if you have a high maintenance fur child like me, I’ve got you covered!! If you trust me with your fur baby, I promise I will love them as much as I love my own!! I work from home, so I have a lot of flexibility. Mornings are more difficult for me, but I can definitely work with you to find what’s best for the pets! My own pets are high maintenance, so I am definitely able to work with your pets needs. I crate my own dog, and give both my dog and cat meds and supplements. I don’t have any human children so my pets are my children. I will give your pet the love, attention, and care I give my own!!
About: I have always had a deep love and affection for animals, and I am lucky enough to have three fur babies of my own. As a pet owner, I understand the importance of finding someone reliable and trustworthy to care for our furry friends while we are away. That's why I am excited to offer my services as a pet sitter. I promise to treat your pets with the same love and care that I give to my own dogs, and will make sure that they are happy and comfortable while in my care. Whether it's walking, feeding, or just providing some extra TLC, I am dedicated to making sure that your pets are well taken care of. If you are in need of a responsible and caring pet sitter, I would love the opportunity to be of service. My husband and I both work from home so we are able to provide bathroom breaks, cuddles and attention all day long for our fur guests. For drop in visits we can come during our lunch hour and right after work! I am able to provide food, medications, love, cuddles, time outside, play time, and make sure they are taken care of to the fullest extent during their visit with my family.
“My dog is very cautious around new people and Shaghayegh has been wonderful with him! She has taken time to get to know his quirks and listened carefully to all recommendations and instructions I have given her in regards to and how to deal with his shyness. She clearly loves dogs and really makes an effort to make their experience enjoyable when they are with her. I highly recommend her!”

About: I have had dogs my whole life and I have had a cat for the last 7 years. I am very good with animals and I love them very much. I have also babysat my own dogs when my parents go away as well as my aunts cats, and my neighbors dogs and cats. Since I've had many animals in my life, I know how to take care of them and I know how to tell what they need. I am in college but have many hours throughout the days that I am available and I am also free most nights (though I would need notice incase I make plans with friends) I am available all day on Mondays, available from 11-2 and after 5:30 on Tuesdays and Thursdays and available all day besides 2-4 on Wednesdays and Fridays. I am also available all day on weekends I would just need to know in advance due to plans. I will offer your pet lots of love and will do whatever is best for your pet! I can easily crate your dog and I love long walks and would be happy to go on one with your pet.
About: I’ve been dog and cat sitting since elementary school, starting with walking my cousins' dogs and caring for them while they were away. I also have extensive experience with feline care, spent hours socializing with friends' cats, and dropped in to feed them when owners were out of town. I work from home and set my own schedule so I’m available for dog walks and cat drop-ins every day of the week from morning through afternoon. When caring for pets I like to follow exact instructions for feeding, potty breaks, and playtime since all pets have their own quirks. I always ensure the home is secure, clean, and locked up before I leave.
“Sherry took our menagerie of dogs and cats in stride when she arrived and she handled my dog Duncan with ease during the walk. She obviously loves animals and my dog, who is sometimes shy with strangers, immediately liked her and will be happy to see her the next time she comes. I highly recommend her if you need a good caretaker for your pets.”

“Thanks Alyssa. Ever since my Wife, his Mommy, passed away in April, his eating and pooping has been off sometimes. We both miss her. When it's hot he will plop down in front of the fan because I turn it on low for him...lol Thanks for taking care of my boy.”

About: Hi, My name is Reina, I recently retired and love to care for pets. I have a lot of time and dedication to care for yours. Flexible with schedules. I am currently retired, so I have a lot of time to play and properly care for your pet. I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours. I have a fence yard and a very clean environment.I do not have pets anymore since my sweet dog passed away.I am ready to give the same kind of love and attention to yours.
About: Thank you so much for taking the time to view my profile☺️ I am a stay at home mom looking to fill her days with some four legged lovin, i am usually available due to me being at home so being available would typically not be an issue! I am VERY well experienced in caring for dogs and cats. I have cared for a variety of animals ranging from senior animals that require round the clock care, to week old puppies needing constant feeding and cuddles, ive cared for sick dogs needing medication, and ive cared for energetic dogs needing someone to run around and tire them out! I have loved and owned dogs my whole life and now that i am an adult i love them even more! My kids share that same love for animals, and we promise to love your sweet baby and treat them like our own🥰 I care for animals full time, so i’m very flexible when it comes to availability! Im always willing to make things work and find a way to help you in caring for your pet! Safety is my number one priority ALWAYS! I will always make sure your pet is safe, happy, and comfortable! I always make sure doors and windows stay closed to prevent an escape, im very diligent in security! I do not have a completely fenced in yard, so i will always make sure to securely walk your dog.
About: 5 Acres, Pool, Large PRIVATE HOME PROVIDING POOCH PAMPERING SECOND TO NONE. Dog boarding, pet taxi, walking or house sitting I do it ALL!! I have over 20 years experience with all sizes and breeds, serving Franklin, Clarke & Western Loudoun Counties in Virginia and Innwood WV. Give your baby a luxury vacation while you are away, a great day-care experience while you work or shop or I’m happy to care for your pet in their own home. Pet taxi service to/from my house, to your vet or groomer is also one of our services. Schedule a meet and greet to come see for yourself. WHY I LOVE DOG SITTING My parents raised Collie's and my first dog was Lady, I was 18 months old! So I have always had dogs, a house just isn't a home without a pup! I have owned, fostered and rescued dogs all my life. I have experience with all breeds, from Great Danes to Yorkies, I have done it! I love dogs, pamper them but give them the boundaries that make them feel secure. SERVICE AREA I am located in a large home with a pool and fenced in backyard in Clear Brook Virginia serving Winchester, Purcellville, Round Hill, Berryville, Bluemont, Hillsboro, Lovettesville and the surrounding areas. We can arrange pet taxi service to/from our home at an extra charge. CALL FOR MORE INFORMATION I’m happy to provide many references from past clients, give a phone and/or in person interview. All boarding clients must complete a meet & greet prior to booking. MEDICATION AND SPECIAL ATTENTION I am trained in administering oral medications and injections. Pet care is my full time profession, I’ve dedicated the past 20 years to watching clients pups so they can work, vacation or travel without their fur babies suffering from separation anxiety, or stress. I have unparalleled experience providing love & attention to my boarders, keeping them happy & safe overnight (or longer) while their family is away. Our pet taxi service can come pick up your baby to start their stay with us or provide excellent transport if your pup has an appointment at the vet or the spa.
About: I have taken care of sick elderly dog. Friends and family rely on me to take care of their dogs or cats or other pets. I have had experience with farm animals. I have taken care of my pet rabbit everyday. I’m open to cats or dogs or any other types of pets, even snakes, I actually love snakes. They’re so cute. I’m a freshman in college, and I am taking a path to becoming a veterinarian. Currently I will not be available, but for me school ends on May 10, so after that I will be home for summer and be available 24/7. We only have a pet bunny, so we built her a hutch that has little side doors and a top that opens up and you can reach her. She has a little house inside the hutch where she can sit inside when it’s cold outside, it’s filled with straw.
About: What sets me apart from other sitters is my lifelong experience with animals, having grown up with dogs and cats in the country. I provide compassionate care for senior pets. My joyful, hardworking, and caring nature for animals ensures each pet receives the personalized attention and love they deserve. I am a flexible and reliable pet sitter available anytime with advance notice. Ready to provide loving, attentive care for your pets whenever you need! I provide attentive care in my clients' homes. For outdoor time, I use a leash to ensure safety and proper exercise. Your pets will receive personalized attention, love, and regular activity.
About: Life is Good with pets! I have been providing professional pet care services for dogs for over 5 years. I have always had different dogs in my life from childhood to adulthood. I’ve seen how happy my own pet is from taking him on regular walks and I am excited to provide this same experience for other pets. I have a large, fenced yard in a semi-rural neighborhood, and I enjoy taking dogs on nice long walks. Pets are allowed on furniture to snuggle and I am also happy to crate train pets, if preferred. I am currently working from home, so I have most of my time to give attention and love to your pet. I am happy to provide these services at all times. I have plenty space and a fenced yard for your pet to play or simple go on potty breaks, if needed. The services requested will be depending on the customers offer :)
About: I have traveled across the USA for housesitting and love it, I continue to do so when my schedule allows. I love the company and exercise. I will treat your animals and your home as my own🐾 Hello there! I'm Elizabeth, and I am a trustworthy house/pet sitter. I have an international e-commerce business which I started in 2006, that my team runs in South Africa, I enjoy just being able to travel around and seeing the different states in the USA. I understand the importance of finding someone reliable to take care of your pets. As an experienced house/pet sitter/walker, also a self homeowner, animal/ pet lover, I will treat your pet like my own. I love animals. Your pets will be in good hands with me, as I am dedicated to providing them with the care and attention they deserve. If you are in need of a reliable and responsible house/pet sitter, feel free to message me to discuss your needs further. I would love to provide you with peace of mind while you are away from home. Or just need an extra hand. Because I travel for business I don't currently offer dog/pet sitting from my own home or house. I can stay in or do drop in visits and walks. I have done this throughout the USA in different states, it has been a great adventure.
About: I have been animal sitting for almost 9 years now, starting when I was in high school. I have experience in animal care for multiple species, energy levels, behaviors, ages, and health needs. No task is too big for me, my biggest job was being a sitter for a family of 10 dogs, and a pig! I worked at a nonprofit animal rescue where I learned more about how to care for cats and dogs, and how to gauge their personalities, and energy levels. I am passionate about animal happiness and satisfaction. Right now, I am completely free. I have a car and a valid drivers license. I just moved back home after hiking for 4 months on the Appalachian trail, while walking I had lots of time to think about my passions, and of those are animal welfare, care, and personally staying active and fit! I have two personal dogs, one of which is a senior in hospice care, out of respect for him, I am not taking animals into my home right now. However, any type of drop-ins or house-sitting is on the table. I take direction seriously and can provide medical care, activity, play, feeding, or anything else that is needed for your beloved animal!
About: Hi! My name is Samantha, and I have over 6 years of experience caring for dogs, cats, and even reptiles of all ages and personalities. Animals have always been a huge part of my life, and I treat every pet like they are my own. I currently have two dogs and a cat, so I understand the importance of patience, structure, and lots of love when caring for pets. My home is pet-friendly and safe for boarding, and I also offer in-home pet sitting so your pets can stay comfortable in their own environment. Since I have open availability, I am able to provide flexible scheduling, last-minute bookings, and consistent care when you need it most. Whether it’s walks, drop-ins, overnight stays, or extended care, I’m always available and committed to making sure your pets feel safe, happy, and loved while you're away. I look forward to meeting you and your furry (or scaly!) family members! My schedule allows me the flexibility to fully be with your pets if I am boarding or need to drop in. When your pets are with me I like to make sure we’re having fun! Safety and trust are my top priorities when caring for pets in my home or in a client’s home. I provide a clean, calm, and secure environment while following each pet’s normal feeding, walking, and care routine. Pets are always supervised, introduced safely to my animals if needed, and kept comfortable and stress-free. I also provide regular updates and photos so owners feel confident and at ease while they are away.
About: Every neighborhood ive lived in neighbors have come to rely on me to treat their pets as well as i would take care of my own family. I love any and all breeds and people call me the dog whisperer haha but joking aside i truly love these animals and would love to car for yours. I make sure that they feel comfortable get exercise and have ample bathroom breaks the same way i treat my own 3 fur babies at home. Any regiment you want me to follow i will follow to a T. and the best part is there is no breed too big; if you know me the bigger the head the bigger the love haha. But my small babies are always just as important. I am currently a stay at home mom so school hours are wide open and despite a few week day evenings being booked, overnights are highly available. In my home we have a fenced in backyard and 3 dogs who all have their own amenities including bowls, beds, toys, cages, and the more. My dogs are family to the fullest and are treated as such. it fits in between kids activities, errands, and school. It allows me to be flexible in what is needed. I just love meeting new fur babies ! My three dogs spend a lot of time inside it is just what is comfortable for them. I also have a fenced in backyard that they do enjoy.
The median cost per walk for dog walking in Winchester is $20
Dog parents share their Rover experiences - Winchester
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.
How to book dog walking

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 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 of Dog Walking in Winchester on Rover is $22 per walk as of October 2026. Most bookings cost between $9 and $27 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 October 2026, there are 810 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 , 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 , 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 .
Yes, you can find walkers who have experience with handling special pet needs in Winchester. On Rover:
- 92% of walkers can help with special care needs
- 94% 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 .
walkers on Rover set their own , 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.



