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

Over 70 pet parents in Winchester have booked dog walking
Winchester, Find top rated dog walking
About: I have always been passionate about helping and caring for people and animals. I have care experience with many breeds and types of animals, including dogs, cats, birds, rodents, reptiles, and horses. I adore dogs especially — their friendliness, loyalty, and energetic demeanor is contagious, and I love them so much for it! My dream is to rescue animals and help to find their forever homes. I will love and care for your pet(s) like my own. As for more about me, I am originally from Kentucky, and I studied music, specifically opera, all throughout college. I am a singer, actress, model, chef-in-the-making, fitness guru, social media influencer, artist, writer, and much more. I enjoy meeting new people and animals, and my greatest goal in life is to help as many others, human and animal, as I possibly can! I am able to check in as early at 9am, and as late as 9pm. I often have my children with me, and they either wait in the car or join us for walks in their stroller. I like to gather as much information from you as possible so that I can recreate your pet’s daily routine while you’re away! I enjoy giving animals the best, most comfortable and familiar experience as possible.
“We are so blessed to have found Maria to walk our dog, Aria. She's been walking Aria 3-4 times a week for a year now, and she loves Aria like she's her own. I could not speak more highly of her. We love, Maria!”

About: I have been caring of a variety fur babies since I was a kid. I have experience with working with both younger and older fur babies. I am currently working while coming my masters online in counseling so I do have flexibility with working overnights. If need more availability please contact me. I have a fenced area at my apartment complex for dogs if needed. I have a variety of treats and toys for cats if needed.
About: I am a certified professional dog trainer and was a veterinary assistant for over 8 years. I have over a decade of experience caring for animals large and small. I have ample experience caring for pets with mobility issues, incontinence, kidney disease, diabetes, anxiety, or other illnesses. I can provide gold standard care regardless of your pet's needs- including oral, topical, or injectable medications, subcutaneous fluid therapy, or just being a patient and calm friend to a fearful friend. I love and care for dogs and cats equally! I currently work a full-time 9-to-5 but have a somewhat flexible schedule within those hours. Early mornings, lunch breaks, evenings, nighttime checks, and weekends are all available options. If taking your pet out of the house, I like to have a fit check of your leash/harness or collar setup first. If your pet is known to be a "houdini" who can escape their gear, I may recommend alternatives and can help you with fitting your pet appropriately and/or bring a second form of containment with me (such as a slip leash used at vet offices) to ensure your pet's safety.

“Sloane is an absolute gem. She is conscientious, dedicated, and thorough. She takes care of our basket-case of a rescue dog several times per week and has been our savior from the ridiculousness of his unending energy and anxiety while we’re away. Her report cards are filled with humor and have us laughing out loud every time. Cannot recommend her enough!”


About: I grew up with three dogs, so taking care of pets has always been a part of my life. I genuinely enjoy being around animals, whether it’s spending time with dogs, visiting cat cafés, or stopping by the humane society to hang out with the animals there. I’m patient, dependable, and I’ll make sure your pets get the attention, care, and love they deserve while you’re away. Have also house and plant sat for people over the years and always enjoyed helping out. I work full time, so I have a consistent routine and know how to manage my time well. I’m available before and after work, on my days off, and can work with pet owners to make sure their pets stay on their normal schedule. I’m reliable, communicative, and committed to giving every pet the care and attention they deserve. I care for pets by following their normal routine as closely as possible and making sure they feel safe, comfortable, and relaxed. In a client’s home, I respect their space, keep doors secured, follow feeding and medication instructions carefully, and provide plenty of attention, exercise, and fresh water. I also like to send updates and photos so owners know their pets are happy and well cared for while they’re away.
About: Greetings, valued customers, my name is Jordan. I appreciate you viewing my profile to get to know me a little better. I kindly ask that you read my profile in ENTIRETY so you have a better understanding to determine if we are a great fit and for detailed scheduling information down below. I look forward to hearing from you and I'm delighted to be here for all your animal care needs. I have cared for fish, dogs, cats, parrots and other birds, bearded dragons, snakes, chickens, goats, bunnies, doves, mini horses, pigs, other farm animals, and other reptiles, amphibians and exotic animals. I have been offering animal care services for eight years, and I completely love and enjoy doing it. The love that animals have for humans is an incredible thing to experience. Caring for animals makes my life so much more meaningful, and I love doing it for people who need my services. Also, knowing that people need my animal care services, fulfills my passion for helping others in life. I love and enjoy being of service to others, and it makes me so happy to be able to do so. I'm currently working as an RBT (Registered Behavioral Technician) (I work with people with autism and help them better adapt to everyday life), and I work with Rover as a petsitter as well. If you contact me for a lenghty petsit, I am able to ask off work with no complications (with more than a 2 week notice), however if you are in need of a speedy petsit, I can work with your schedule (but I may have to work a few hours during the day on week days, with no complications). My Rover calender will reflect my availability will continually be updated. Please check the calender before reaching out. Thank you for your understanding. I prefer going to a client's house to take care of their animals in a familiar environment, along with a detailed list of instructions of do's and dont's for their pet. Instructions on animal care are to ensure the animal's safety when they are with me, without me needing to unnecessarily contact and bother the owner while they are away. Also, a general list of outdoor activities I can do with the pet is welcome. For example, if I can take the pet hiking, to the park, for walks, etc. Also, does your pet get along with other animals, children, or people well, and does your pet get car sick? These variables are essential information for me to know to ensure the best care while you are away. My passion is pets, and I want to ensure your pets are comfortable and safe with me, so I highly encourage more than enough information on caring for your babies. Please note if your location is 40 miles, plus, in distance from my Rover given location, I charge for milage, for the traveling/distance in the initial reservation contact message for meet and greets. I will send you a new quote to your initial request for these changes in price due to milage charges. Thank you for understanding this policy.
“Rachel is the first dog walker I’ve ever hired, and my first experience with Rover. She has been exceptional. SO sweet, great at communicating, and timely. She also spent an extra 20-30 minutes walking my dog (after communicating to see if it was ok), trying to track down a bandana that had fallen off. She has been a huge help to my family, and I can’t recommend her enough.”

About: After experiencing the tragic loss of my own cats due to a negligent pet sitter, I became deeply committed to providing the highest level of care for all animals. That experience taught me how vital it is to entrust pets to someone who not only understands their needs but treats them like family. I specialize in senior pet care, offering compassionate support for aging pets, including administering medications, managing health conditions, and providing gentle, tailored exercise routines. I also have experience training puppies, helping them develop good behaviors early on and ensuring they have the structure they need to thrive. My focus is always on building trust and creating a safe, loving environment for your pets, so they feel comfortable and secure when you're away. Above all, I aim to offer peace of mind to pet owners, knowing their animals are in caring, responsible hands. Available almost anytime in Lexington and surrounding areas contact in advance is recommended but we can take last-minute calls depending on the situation and what not. Also I work with you budget! I have a park near me and I do take my own dog to the dog park every chance I get via Lyft and plenty of toys for your fur babies!
About: Hi, I’m Claire! 🐾 Growing up, my house was basically a mini zoo—in the best way. At any given time, we had at least three cats, two dogs, and a rotating crew of fish, rabbits, and guinea pigs. I was raised on animal love and responsibility. Now, I bring that same lifelong care to every pet I meet. I truly treat your pets like they’re my own—with belly rubs, cuddles, playtime, and lots of attention to their unique needs. Whether your pup is high-energy or your cat just needs a quiet place to nap, I’ve got you covered. Your pet won’t just be looked after—they’ll be loved, spoiled, and safe. I can’t wait to meet your best friend! I work full time during the week, but come Friday, I’m all yours. I’m most available Friday evenings through Sundays, which makes me a perfect fit for weekend getaways, last-minute plans, or just giving your pet some extra love when you’re busy. With a lifetime of experience raising dogs, cats, rabbits, guinea pigs, and fish, I know how to tune into each animal’s needs and personality. Whether your pup loves a long walk or your cat prefers a calm cuddle buddy, I treat every pet like they’re part of my own family. Need someone dependable, loving, and experienced to care for your pet over the weekend? I’d love to help! In your home: I’m respectful of your space and follow your instructions closely—whether it’s meal times, favorite toys, medication routines, or little habits that make your pet feel most at home. I make sure they get plenty of attention and comfort while you’re away, so you can relax knowing they’re in good hands.
About: I’ve loved caring for my friends and family’s pets for many years, so now I would love to love and care for your pets as extra income I work full time M-F, often weekends I am available for overnight stays, or throughout the week on my lunch for a 30 minute walk I take care or your pets and your home like they are my own. I love animals but don’t have any of my own due to living in a small apartment so I would love to come visit yours!
About: Hi! I am a traveling healthcare professional working in Lexington looking to care for some fur babies! Depending on the distance I am available for overnight stays. I am available most weekends and some weekdays. I have 2 cats! I’ve had experience with dogs, cats, birds, small animals, fish, and some reptiles. I do work a full time job during the week. 12 hour shifts in Lexington. My weekends are available and weekdays will vary depending on my schedule. My cats are indoor. I do have one leash trained and we do take walks. One requires eye drops daily. 2 pet feedings per day as well.
About: I had cat and dogs my whole life and owners pets mean the word to them care and gentleness mean the word to them I love pets I am available every day if you need your pets taking care of at anytime of the day you can get hold of me and I make sure I am there If you have any requests for your lovable pets let me know I will do my very best to make them comfortable as possible at all times
About: My experience with dogs isn't just a hobby; it's a core part of my daily life. As a proud dog owner myself, I have years of firsthand, 24/7 experience managing everything that comes with a happy pup—from daily walks and feeding routines to understanding dog behavior and, most importantly, giving plenty of love and attention. I also have experience providing overnight care for other people's dogs. I know how important it is to create a calm, safe, and comfortable environment for a dog in a new space, and I'm committed to maintaining your dog's schedule to make them feel secure and right at home. I am currently a college student and I am looking to earn extra cash over my breaks when I am visiting home and I do have a lot of free time. When your dog stays with me, they are treated like a member of my own family. My goal is to be their "home away from home."
The median cost per walk for dog walking in Winchester is $18
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 4 repeat dog walking clients
FAQs for Dog Walking - Winchester
Frequently asked questions about Rover
The average cost of Dog Walking in Winchester is $20 per walk as of October 2026. Most bookings cost between $13 and $28 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 October 2026, there are 714 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:
- 91% of walkers can help with special care needs
- 95% can help with giving oral medications or injections
- 96% 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.

