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

Over 146 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.
“Just wonderful, haven’t been able to meet up yet,(work work work )however very wonderful communication and updates she comes to let my my pup out and give her a little energy release on my 12hr shifts. Quick responses and overall feelings of trust with a person coming into my home! She even makes sure to tell me what my cat was up to when she visits. Nothing but great experiences with her!”

“⭐️⭐️⭐️⭐️⭐️ A True Gem – Like Family to Us and Maximus! We feel incredibly lucky to have found Hannah—she’s not just a dog walker, she’s part of our family. Our dog Maximus is truly our baby (especially now that our kids are grown and out of the house), and knowing that Hannah cares for him with the same love and attention we do means the world to us. Hannah has been with us for over three months now, and in that time she’s become someone we fully trust with our most spoiled and beloved family member. She’s reliable, flexible with our crazy schedule, and always greets Maximus with affection and warmth. You can tell she genuinely loves what she does. Maximus absolutely adores her! She goes above and beyond to make sure he feels cared for when we’re not home, which gives us such peace of mind. We treasure Hannah and everything she does for our family. If you’re looking for someone who will love your dog like their own, look no further. She’s truly one of a kind.”

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: Available in evenings and weekends. I am reliable, responsible and always on time. I love all dogs and I appreciate all the quirks that come with their individual personalities. I have loved animals since I was young, and I volunteered for a pet shelter in the summer when I was younger. Although I am currently a cat owner, I love all furry animals and I have to greet every dog I meet on the road. I am looking for part time work and this would be a great opportunity to utilize my free time and my love for canines and kitties. I have three cats that are basically like my children, but I adore dogs and would love the opportunity to interact with them daily or weekly. I have free time on my work from home days as well as weekends to assist other dog/cat owners. I do not have a fenced yard, but I live in a community that has a lot of pathways and green space. Within my apartment, I can keep my cats separate if needed but happy to let the dogs explore and get comfy in my space. I am very courteous of other people's space and preferences.
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.
“Meghan is amazing! My 6 year old mini golden doodle never had a babysitter she didn’t know previously, and I was so nervous going out of town and leaving her. Meghan was so responsive and professional- I felt so much more at ease after talking with her! I got photos of their walk together and it made me so happy to see my dog having so much fun!”


About: I have been a pet owner for most of my life. I volunteered at the SPCA while I was in college, and I thoroughly enjoy interacting with animals. I will care for yours as I cared for my own! While my daughters are in school, my day is open! I can visit, walk, and play with your pet while you’re at work, so you won’t have to worry if they’re bored or lonely. I will come to your house to walk, feed, and/or play with your pet. We can discuss your pet’s needs at any time.

About: Hi! Paloma** 🐾 I’ve had dogs for year, three, in fact, over the course of my life. I recently said goodbye to my last pup, and while I’m not ready for a full time dog in my home just yet, I miss it all deeply: the walks, the game of fetch, the pure joy and love only a dog can give. I am not new to dog care, I’ve looked after many dogs over the years, but this is my first time doing it through Rover! I’d love the chance to give your pup some of that same love and attention while you enjoy a vacation, work trip or time away. I treat every dog like my own, patient, attentive, and always up for a good walk or a solid game of fetch. Looking forward to meeting you and your pup! I work 9-6 hybrid, Monday thru Friday with somedays being fully remote. I am home most weekends and spend my free time walking, doing arts and crafts or gardening. Peace of mind is definitely important when it comes to my fur babies, I know that first hand. I can send check in photos with every walk, treat and meal if that is what you wish. I like to also take them to the dog park in my neighborhood if they play well with others. 3 walks a day minimum will be provided unless more are required. I currently working on building a fence to m a backyard and should be completed but end of September!
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: Hello, pet parents! My name is Jessica, and I bring over 25 years of dedicated experience working with both dogs and cats. As a professional dog groomer for the past 15 years, I have developed a keen eye for pet care and well-being. At home, I share my life with a delightful trio: a standard poodle, a lovable pit bull, and a majestic Maine coon cat. Each of them has taught me unique lessons in care, patience, and the joy of pet companionship. Why choose me? • Decades of Experience: With 25 years of hands-on experience, your pets are in knowledgeable and capable hands. • Groomer’s Expertise: My grooming background ensures your dog not only gets a great walk but also some extra TLC, including coat checks and paw care. • Personalized Care: I understand that every pet is unique. I tailor my services to meet the specific needs and personalities of each furry friend. • Safety First: Your pet’s safety is my top priority. I am trained to handle various breeds and temperaments with care and professionalism. Let me provide your pets with the exercise, attention, and love they deserve. Book a walk today and see the difference an experienced and passionate pet professional can make! I’m a professional dog groomer with a flexible schedule that allows me to provide dog walks and drop-in visits throughout the week. I enjoy using my available time to give pets the exercise, attention, and dependable care they need while their families are away. Your pet’s safety and comfort are my priority. With 25+ years of experience caring for dogs and cats and 15 years as a professional dog groomer, I’m comfortable working with pets of many breeds, sizes, ages, and personalities. During drop-in visits, I can provide potty breaks, feeding, fresh water, playtime, and medications as directed. I also offer dog walks tailored to your pet’s individual needs.
About: I am a husky lover and owner who has spent most of my life taking care of dogs! I am 30 years old and have grown up taking care of beagles as well as pet sitting for family members and neighbors. Now, I currently have two huskies, ages 3 and 1. I enjoy long walks with my pups and lots of play time! On the weekends, I enjoy taking my dogs on long hikes, taking them to the dog park for some play time and even runs on the beach. My huskies are friendly with dogs their size and love making new friends. They also have spent time around cats and although they avoid playing, they do love other furry friends. My energetic attitude and love for animals makes me the best match for the job.
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: Looking for a trustworthy dog sitter? You've come to the right place! As a Critical Care Veterinary Technician, caring for animals is more than my career, it's one of my favorite passions. Your pet's safety, comfort, and happiness are always my top priorities. Whether your pup is energetic and loves to play, prefers a quiet place to relax, or has special medical needs, I'll provide personalized care tailored to them. I know how important it is to leave your furry family member with someone you can trust. That's why I'll treat your dog like one of my own, with plenty of love, attention, exercise, and cuddles while you're away. My goal is to make every stay as comfortable and stress free as possible, so you can enjoy your time away with complete peace of mind. I look forward to meeting you and your four legged best friend and becoming their home away from home! Rover is currently a fun side hustle, it helps keep me from buying more animals at the moment! I am available for meet and greets around your schedule. I currently do work full time as a critical care veterinarian technician at an emergency vet hospital 3 days a week. I was a large animal veterinarian assistant prior to transitioning to small animals! I grew up on a working ranch, so I can assure you your animals will be in great care! I try my best to be accommodating to last minute bookings and I can always adjust my prices to your needs! Daily updates are absolutely always included, I will always send pictures. I keep my phone on ring at all times so you can rely on me for a prompt answer. I take safety very seriously and will always accommodate to your pets needs.
About: I’ve taken care of dogs since I was a child. My family and I grew up with a family dog and then got a puppy in high school that we trained. Even would watch the neighbors pets when they went away. Most recently, I have watched/stayed with a dog when the family traveled. Love all animals, but especially dogs! I work from home and on my own schedule. I have the flexibility to take dogs on walks, bathroom breaks, and even stay with the pet when needed! Working for yourself has great perks when it comes to taking care of our lovely pets. I live in an apartment complex, but have sidewalks for walks. We also have two dog parks. I love staying active, so walks for me are enjoyable! I don’t have any pets of my own currently, so I love being able to love on others pets!
About: Im very excited to take care of your dogs! Ive taken care of animals since i was 11 years old! If you’re interested in me walking your dog message me and we can talk more about what youd like! im currently free almost everyday! im using this to make extra money and i dont have many plans coming up so it fits almost everyday! I can sit with your animals or do any extra thing that is asked! I can put them in the crate or other places if thats where they need to be.
About: Since the age of 8, I've cared for a variety of dogs and animals. As a dedicated animal enthusiast with extensive experience, I know the significance of finding the ideal pet sitter, ensuring your beloved pet receives the love and care they deserve. I am self employed and have an extremely flexible schedule. I understand that life can be unpredictable, and plans may change. I am reliable and flexible, accommodating your schedule to the best of my ability. If you need to make any adjustments to the agreed-upon schedule, I will do my best to accommodate your needs. Creating a good environment for your pets is essential for their overall well-being. I will create a warm and welcoming atmosphere that promotes their happiness and comfort. This includes providing stimulating activities, cozy resting areas, and plenty of love and affection. I am attuned to your pet's emotional needs and will ensure they receive the attention and care they deserve. In addition to providing exceptional care, safety, trust, and a good environment, I also offer regular updates and open communication. You can expect timely updates on your pet's activities, behavior, and overall well-being. I am always available to address any questions or concerns you may have, as I believe in transparent and reliable communication. As your pet sitter, my goal is to provide a stress-free experience for both you and your pets. With my commitment to optimal care, safety, trust, and a good environment, you can enjoy your time away knowing that your furry friends are in capable and loving hands.

About: I've taken care of multiple types of animals over the years! Dogs, cats, birds, bugs, reptiles, rodents, amphibians and fish! Much of my experience comes from working at PetSmart and owning most of these animals myself! I have 2 Rottweiler/Husky mixes, 2 cats, a cornsnake, 5 birds (Sun Conure, Green Cheek Conure, Cockatiel, and 2 Budgies!), 3 axolotls, one tank of Koi and Goldfish, and another tank of tropical fish! I currently work part-time at PetSmart as a pet caretaker! I have Thursdays off, but my work schedule doesn't normally get in the way. I always wait for an animal to greet me first to avoid stressing the pet out. I normally have calming chews and treats on me to try to encourage the animal that I am not a threat.
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?
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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 is $22 per walk as of November 2026. Most bookings cost between $11 and $27 per walk. On Rover, 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 November 2026, there are 814 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 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:
- 92% of walkers can help with special care needs
- 95% can help with giving oral medications or injections
- 99% 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.








